Derek Shepherd

"Yes or no. In or out. Up or down. Live or die. Hero or coward. Fight or give in. I'll say it again to make sure you hear me. The human life is made up of choices. Live or die. That's the important choice. And it's not always in our hands."

- Derek Shepherd

Derek Shepherd was an attending neurosurgeon and board director at Grey Sloan Memorial Hospital. He was married to Meredith Grey and they have two daughters, Zola and Ellis and a son, Bailey.

Early Life
Derek spent most of his life prior to his arrival in Seattle in New York City. As a child, Derek had no hair products, so he had a large afro, acne, a weight of 110 pounds, and played the saxophone in the school band. He was raised by a single parent, his mother Carolyn, along with his four sisters: Nancy, Kathleen, Liz, and Amelia. Like Derek, all four of his sisters are doctors. His father owned a shop when he was younger, and one day two robbers approached him and demanded that he give up the watch his wife Carolyn had saved tirelessly to buy for him. When he refused, the robbers shot him to death, with Derek and his younger sister Amelia bearing witness to his death while hiding in the closet. This event forms a large part of Derek's moral compass, and consequently may have inspired him to become a surgeon to help save lives. As a result he is especially cynical when treating criminals and feels that they do not deserve any compassion from him.

Derek's childhood best friend was Mark Sloan, who came from a wealthier but emotionally deficient background, and was like a second son to the Shepherd family.

Derek used to ride a motorcycle, but after an accident that gave him a scar, he stopped doing so.

Derek went to Bowdoin College in Maine for his undergraduate years. He then attended Columbia University College of Physicians and Surgeons with Addison and Mark. During his medical education, Derek was taught by Richard Webber.

Leaving New York
After Addison cheated on him with Mark, Derek left his private practice in New York and accepted Richard Webber's offer to come work for him at Seattle Grace Hospital with the possibility of becoming the Chief once Webber retired. Derek became aware that Burke was in the running too, after he was hired. His sudden move to Seattle made him a curiosity to the other doctors as he gave up a well-established and respected practice in New York.

Becoming the Chief of Surgery
While Richard was getting treatment for his alcoholism, Derek became Chief of Surgery. The job required more paperwork and less surgery than he thought, which led to his resignation.

Shooting
Gary Clark was a grieving widower whose wife was taken off of life support. He blamed the doctors who had taken her off of life support. He attempted a lawsuit against the hospital but had no case. Still grieving heavily, he went on a shooting spree at Seattle Grace Mercy West. He killed Dr. Charles Percy, Nurse Vivian, Dr. Reed Adamson, and 8 other people, including 2 security guards. He also shot Alex Karev, Owen Hunt, and Derek Shepherd, along with four others who were injured, but not killed. The stress of witnessing his shooting caused Meredith to miscarry. Derek coped with the traumatic experience by speeding. He was arrested multiple times for speeding, which led to Meredith leaving him in jail overnight. He quit his job as Chief of Surgery, having intended to do so for some time as he realized he preferred to be in the O.R. instead of doing administrative work. He told the psychologist Dr. Andrew Perkins that the shooting gave him the courage to step down and quit. After getting arrested prior to Cristina and Owen's wedding, Meredith told him about her miscarriage and begged him to stop making her worry with his speeding.

Alzheimer's Trial
Inspired by Meredith's mother's disease, Derek decided to try and find a way to cure Alzheimer's. He initially selected Alex to work with him on the trial, but Alex couldn't handle how depressing it was, so Derek asked Meredith to work with him instead. When Richard started to get worried about Adele's mental condition (he knew she had Alzheimer's), he asked Derek to have her put into the trial. She did not get into the trial because her Alzheimer's has not progressed far enough yet, which was shown by a testing. Eventually, she did get put into the trial because of her rapidly progressing disease. Meredith switched the envelopes to make sure Adele got the active agent and not the placebo and in doing, so she tainted the trial. Meredith would have been punished for her actions, but Richard stepped in and took the blame, knowing that she only did what she did because she wanted to help Adele. The trial data was sent to another doctor to continue the work and Derek was blacklisted by the FDA.

Hopeless Cases
Derek came to Seattle with a reputation as a gifted surgeon who had a penchant for taking on "hopeless" cases and highly complex procedures that are often passed on by his peers. After being blacklisted by the FDA for the Alzheimer's trial incident, Derek resumed taking on impossible cases. He took Lexie under his wing and they worked on those cases together.

Plane Crash Aftermath
After having to smash his left hand with a rock to free it from plane wreckage, Derek's hand was severely injured. Many bones were broken and there was significant nerve damage. Callie was able to fix his hand, with the help of the donation of a nerve from the leg of Derek's sister Liz.

The President's Brain Mapping Initiative
Not much time after promising Meredith to take a step back to take care of the kids so she could shine, Derek teamed up with Callie to create robotic limbs that could move through mind control. Derek developed special sensors that had to be inserted in the skull in order for the robotic limbs to work. Upon Owen's request, Derek sat down with guys from the President's brain mapping initiative as they expressed interest in using his sensors for their project too. On top of denying them the rights to his sensors, Derek told them they were approaching their project all wrong and set them in the right direction. Later that day, Derek was called by the President, who asked him to join his brain mapping initiative.

Derek accepted the offer and started working with his new colleagues from his office at Grey Sloan Memorial. He kept contact through video calls. He was shown to be of great value to their project when they bent the rules when he stated he'd quit if they wouldn't let Callie continue to use the sensors too. Initially, Meredith resented the fact that he didn't keep his promise to take a step back, as now she had to take a step back to take care of the kids. As he became more and more important, occassional business trips to Washington D.C. were required. Luckily for him and Meredith, his sister Amelia decided to stay in Seattle, thus being able to take over his service, so that he could brain map to his heart's content, and help them take care of the kids, giving Meredith the time she needed for her career. When Derek returned from one of the trips to D.C., he had met the President, who was so interested that he wanted to make the meeting a weekly thing. He offered Derek a permanent position at the NIH and an attending position for Meredith at James Matheson Hospital, so Derek could do the actual brain mapping work himself.

Meredith initially wanted to join Derek, but Cristina told her that even though Derek is dreamy, Meredith is the sun, not him. Meredith then decided to stay in Seattle as that's where she grew up and started her family, and she didn't want to be a trailing spouse like her father was to her mother. Derek didn't really understand why, as there'd be nothing she couldn't do in D.C. that she would be able to do in Seattle. However, he decided that Meredith and the kids were more important to him and he turned down the job, even though Meredith didn't ask him to.

This rendered him bitter and angry all the time, as Meredith wasn't happy with his choice, never showing that she was supportive of his decision. He pressured Meredith to make the most of her career to make up for the sacrifice he made, which she soon grew tired off. During a heated argument, he compared her to her cold mother, resulting in a radio silence between the two. He also constantly butted heads with Amelia, who took over his job as Head of Neurosurgery. He tried to get his old job back, but later apologized for that. She understood that he gave up a once-in-a-lifetime opportunity, but didn't think that was reason enough to take out his anger on the people around him.

Meredith and Derek only managed to speak to each other in "time-outs" regarding Maggie, whom they discovered to be Meredith's half-sister. He threw a dinner party, but he and Meredith got too wrapped up in a sexual encounter after months of denying him sex to make it in time. While he started to keep himself under control at home, he still had difficulties at work. When a woman spilled Amelia's secrets about her drug abuse history in the hospital, he simply took her case when the woman requested another doctor for her parents rather than supporting his sister and defending her. In the evening, he admitted to Amelia that he lost himself, not recognizing himself anymore. He wanted to do right by everyone around him, but he only ended up hurting them. He was angry and miserable all the time and didn't know what to do with himself anymore. Amelia said that that feeling is what they call rock bottom.

Derek later butted heads with Meredith over a case. She suspected that he did that because of their latest fights. He acknowledged to Richard that she had every reason to think that, but he assured him that it wasn't the case. They both recognized Ellis in Meredith, this time in the sense of the ambitious surgeon. Throughout the day, a personal assistant of the President's came back to Seattle to offer him the job again, but he refused again. The situation resulted in his biggest fight with Meredith just yet, with him stating he was done compromising himself for her. She replied he did, making her feel his pissiness and resentment all day. He explained that was because she never showed support for his decision, instead trying to prove all the time that he made the wrong decision. His recent behaviors made it clear for her that she had proven it, as he couldn't be happy anymore, diminishing everyone around him. "I gave up everything!" he yelled, once again expressing how important the brain mapping initiative was for him. Meredith pointed out that he was the only one keeping him down, as she never asked him to stay, and stated he should've gone do D.C., which he replied was still an option. He took his phone and called the President's assistant, this time accepting the job. He assured Meredith he was really going to leave, and walked off to pack his stuff.

Time in D.C. and Return
Derek went to the airport, and right before boarding the plane, he had a phone call with Meredith. They agreed to stop fighting and try to make it work, as neither of them wanted their relationship to end. He went to D.C. and started leading the Brain Mapping Iniative, aided by research fellows. He took an interest in a side project of one of these fellows, Renee Collier, and encouraged her when she felt stuck, eventually even starting to help out with her research. Renee started to develop a romantic interest in him, which ultimately resulted in a kiss between the two. Derek stopped it, saying he loved his wife and didn't want anything else than what he had with her. He quickly left the lab to board a plane to Seattle to go see his wife, forgetting his phone and keys in the lab. At that time, Meredith called him to talk about her day, and Renee picked up the phone, thinking it was Derek calling with another phone. Renee didn't know what to say after answering and hung up, leaving Meredith to think that Derek was cheating on her.

Death
Not long after his return home, Derek was on his way to the airport for one last trip to D.C. when he witnessed a car crash on a remote road. He immediately leaped into action, saving four people from the wreckage before the emergency officials arrived to take the patients to Dillard Medical Center. Derek returned to his car and began to pull out to turn around when his phone suddenly rang. Leaving the car sideways in the middle of the road, he began reaching for the phone, not noticing an approaching semi, which crashed into the side of his car. Derek was then taken to Dillard where the doctors began examining him. Conscious but unable to speak, he knew that he needed a head CT, and begged in his mind for the doctors to also realize this, but to no avail. Derek was rushed to the OR, but by the time the doctors figured out what was going on and managed to bring in a neurosurgeon (whom they had to wait for over an hour after paging him), it was already too late and Derek was pronounced brain dead. Not long after, Meredith, whom the police have brought to the hospital, signed the papers to take him off life-support. She then sat with him as he died, holding his chest and telling him "You can go" as he let out his last breath. Interestingly, he continued to narrate in his mind up to almost the very end, even after losing consciousness (and possibly all brain function) -- at one point saying to the attending physicians "It's too late." "You're too late." We are left with the feeling that at some point an ethereal consciousness had taken over where his physical brain was no longer capable.

Personality
Although he is sometimes annoyed by his overbearing mother and sisters, he is nonetheless aware of their closeness and has no doubt that all four of his "very girly" sisters would be at his bedside if he were ever hurt or sick. He said that he chose surgery as his specialty for the quiet escape and solace of the O.R. His profound hurt over Mark’s affair with Addison back in New York is compounded by his view of Mark as his brother, the one constant male influence in his life since the death of his father as a child. Probably due to his own background and experience of growing up in a large, happy family, he was much more open to meeting Meredith's "long lost" half sisters than she was. He had to encourage her to accept Lexie Grey and Maggie Pierce into her life. He took Lexie under his wing and she saw him as the "big brother" she never had.

Contrary to the lifestyle his salary entitled him to, Derek preferred the simple life and lived in a trailer, much to Addison's horror and everyone else's bemusement, prior to moving in with Meredith. He tried to eat healthy despite his hectic schedule and irregular hours and enjoyed being in nature, especially fishing.

In contrast to the easy going Mark, Derek tends to brood. After working on Jen Harmon, who died on his O.R. table, he spent several weeks hiding out in his trailer. He also tends to hold grudges, as shown when he brought up Addison's affair in a heated argument with Mark and the fact that he still has lingering anger over his father's murder.

Derek tends to have high and exacting standards, sometimes yelling at interns and residents for not meeting them. Although charismastic, his reputation has been known to intimidate the newcomers. However, he is also liked by interns and residents due to his willingness to teach and allow them hands-on experience in his surgeries. He dislikes the competitive "dog eat dog" attitude displayed by some of the residents and has been known to threaten severe consequences or throw out residents and interns who try to get in on his surgeries through such means.

At Seattle Grace, he managed to stay friends with Addison, even after their divorce, and was friends with Preston Burke, but was left without friends when they both left Seattle Grace Hospital. He was broken up with Meredith, Bailey didn't want to have a drink with him, and the Chief said he didn't drink. With nobody to talk to, Derek started to talk to Mark again, and they slowly began to rebuild their friendship and soon enough became best friends again. After getting back together with Meredith, he became friends with her housemates and friends, primarily Cristina, Alex, Izzie, and George. They were initially antagonistic towards her as they thought she was sleeping with him to get into the O.R. but they quickly accepted him after getting to know him. Derek befriended Owen Hunt due to his relationship with Cristina, Meredith's "dark and twisted sister". After a rocky start to their working relationship, they shared a mutual respect for one another and sometimes hung out with Mark, especially when they have "girl problems".

When Richard began slipping back into the state of a severe alcoholic, Derek was adamant on Richard seeking treatment for his condition, even if it meant jeopardizing Richard's career in the process. When the hospital board learned that he'd begun drinking again, they presented to him the option of retiring. Derek, on the other hand, stood by the plan that Richard enter a rehab program, sober up, and return to his position as Chief of Surgery. While still in denial of his predicament, Richard accuses Derek of forcing his problems out into the open so he could get his hands on the position as Chief. While Derek admitted that he did want the job, he still stood by the plan of Richard entering rehab so that Richard could eventually return as Chief. In Richard's absence as chief, Derek assumed the role temporarily.

Addison Forbes Montgomery
Derek married his medical school girlfriend, Addison Montgomery in 1994, and the two began their residencies, studying under Dr. Richard Webber. Following residencies and fellowships, Derek and Addison quickly became very successful in their respective fields. They appeared to lead an affluent lifestyle, owning both a Manhattan brownstone overlooking Central Park and a home in the Hamptons, as well as running their own private practices. However, their success and busy workloads put a strain on their marriage, and the two grew apart; the emotional distance eventually drove Addison to cheat on Derek with his best friend, Mark. Derek himself admitted that he was never around. After discovering Addison in bed with Mark, Derek declared the marriage over and relocated from a private practice to Seattle Grace Hospital, accepting a job offer from his former teacher, Dr. Richard Webber, as Head of Neurosurgery at Seattle Grace Hospital and trading in the brownstone for an Airstream trailer on 40 acres of rural property on Vashon Island.

Meredith Grey
Soon after arriving in Seattle, Derek met his future wife Meredith Grey at a bar and went home with her for a one-night stand, only to discover the next day that she was a new surgical intern at the hospital. Although she initially rejected his advances as inappropriate due to their working relationship, Meredith eventually agreed to date Derek, although he failed to tell her about his marriage. His charismatic, charming personality and good looks earned him the nickname “McDreamy” among Meredith and her friends. However, their fledgling relationship came to a sudden halt when Addison arrived in Seattle for a consult upon Richard Webber's request. Addison had also brought divorce papers, but made it clear that if Derek was willing to give her a second chance, she wanted to give their marriage another try. Derek struggled over his choice, but ultimately, his sense of obligation to his marriage vows won, and he left Meredith to return to his wife.

After a 17-day vacation, Meredith and Derek saw each other for the first time since Burke and Cristina's wedding and they both met Meredith's half-sister, Lexie. Later, Derek pulled Meredith aside to ask if their relationship was over, and she said it was. However, they ended up kissing and having "break up sex". They later said that their relationship consisted of S&M (sex and mockery) only. Derek, thinking about his addiction to have sex with Meredith, told her that he wanted more; he wanted to marry her and have kids with her, to build them a house and have them settle down and grow old together. He wanted to die in her arms when he was 110 and he wanted them to have a lifetime. Meredith, as she was, said she needed time and walked away, but they continued to have sex. Throughout this, Cristina helped Meredith with her relationship and tried to help her find out what she wanted.

Meredith asked him to live with her, which he agreed to, saying she was flighty like a deer and that they would take baby steps, showing he would show her all the patience she needed. He wanted to force Alex and Izzie to move out, but Meredith didn't, telling him they were her family. However, he said they could stay and that, once again, he would wait until she was ready. When he discovered her mother's diary, he had a conversation with Mark, where his friend asked him about the trailer. He answered that he was more likely to be kicked out by the end of week, so he keeps the trailer, but she wanted him to stay, so he lends her his trailer so she can read the diary with Cristina, stating that she needs a place where she can be alone.

Sydney Heron
Although Derek and Sydney were physically close, they weren't yet emotionally close or in an actual relationship. After Derek went on a pity date with Sydney Heron, Meredith was concerned about him dating other women, so she announced to him that she didn't want him to see other women, and even if she wasn't enough for him right now, she was trying and was scared that she would lose him.

Rose
She told him not to say anything yet, so he was unable to tell Meredith that he had just kissed Rose, a nurse who he'd been getting to know and flirting with over the last few days. When Meredith discovered that he had kissed Rose, their relationship ended.

Derek began to date Rose and Meredith entered into therapy with Dr. Wyatt. While Derek appeared to be happy in his relationship with Rose, it was clear to those close to him, namely Mark, that he wasn't. Derek delayed sleeping with Rose and after finally doing so, he admitted to Mark that he had been thinking of Meredith the entire time. Everything finally came to a head when his and Meredith's clinical trial finally saved a life. He tried to find her to celebrate the good news and eventually located her on his land. She had built a house of candles and told him that she was now "all whole and healed" and that while she hadn't forgiven him, she wanted them to be "extraordinary together rather than ordinary apart." They kissed before he left to break up with Rose. Rose was angry at him over the break-up, accidentally stabbing him once with a scalpel in the middle of a surgery, which led her to transfer departments.

Familial
Family is something that is very important to Derek. His decision to work on his marriage was based largely on his sense of obligation to Addison as his family, the woman with whom he shared "eleven birthdays, eleven Thanksgivings, and eleven Christmases". The choice was not as simple as Derek had anticipated, and he found that he still had very strong feelings for Meredith, even as he tried to repair his marriage to Addison. Shortly before Christmas, he confessed to Addison that Meredith had not just been a fling, but that he'd fallen in love with her; Addison was willing to wait it out, although the situation was complicated further when she and Derek took in Meredith's dog, Doc. Although Derek eventually admitted that the problems in their marriage were partially his fault, his love for Meredith continued to make him emotionally distant from Addison.

When Meredith began dating Finn Dandridge, Doc's veterinarian, Derek became so withdrawn and consumed with jealousy that Addison confronted Derek about his ongoing infatuation with Meredith, and even asked Meredith if she was sleeping with Derek. At a hospital-sponsored prom for the chief's dying niece, Derek and Meredith's emotional affair reached the point of no-return. After a heated argument in an exam room, Derek and Meredith had sex, but before they could discuss the implications of their actions, Meredith was called away to deal with Izzie, whose fiancé had just died. The next day, Addison found Meredith’s panties, which had been left in Derek's tuxedo jacket, and pinned them to the hospital bulletin board, while Derek went to Meredith's house and professed his love to her for the first time. Their reunion, however, was not immediate.

Initially, Derek felt immense guilt over the breakdown of his marriage with Addison, and went to the hotel room where she was staying to apologize. Instead, he was appalled to find out that Addison, in a drunken stupor, had called Mark in New York to fly to Seattle for a "trans-continental booty call". To Derek's disdain, Mark decided to take up a position at Seattle Grace in a bid to woo Addison back. Although he and Addison acknowledged the end of their marriage and began divorce proceedings, Meredith was less certain, and decided to date both Derek and Finn before making a decision between the two. While they were dating, Meredith was admitted for an appendectomy, and Finn's concern for her during her illness led Derek to reconsider his pursuit of her. As she recovered from surgery, he told Meredith that he was walking away, freeing her to be with Finn, whom he considered "the better guy". Meredith, however, had already decided that Derek was "the one" for her, and broke up with Finn. She kept the break-up from Derek for another week, and made the unfortunate timing mistake of telling him just after Addison had confessed that she and Mark had not just been a one-night stand, as she had led Derek to believe, but had actually lived together for two months after Derek left for Seattle.

Nancy Shepherd
Meredith's introduction to Derek's family was no less problematic; she stopped by the trailer one night to talk to Derek and discovered a strange woman lying across Derek's bed and Derek, wearing nothing more than a towel and a very startled expression. She would later learn that the woman was Derek’s sister, Nancy, but the explanation of the misunderstanding did not make Meredith any more appealing to Nancy, who continuously referred to Meredith as the "slutty intern". Derek defended Meredith, leading Nancy to acknowledge Derek's feelings for her, but Nancy encouraged her brother to take some time to figure out what he wanted rather than worrying about the women in his life.

Following Nancy's advice, Derek asked Meredith for time to take some space for himself, and then embarked on a very brief camping trip, which only cemented his desire for Meredith. He found her in the very place they had first met—Joe's bar—and they agreed to start their relationship over from the very beginning. While their newly resumed relationship was happy to begin with, Derek and Meredith began to grow distant after she almost drowned. As the distance between them grew, Derek was tempted to accept a drink from a woman he met at Joe's during Burke's bachelor party, but ultimately refused. The next day, he admitted meeting the woman (who unbeknown to both, was Meredith's half-sister Lexie) to Meredith and confronted her over her level of commitment to their relationship. He told her she was the love of his life, but asked that she end the relationship if she was not equally committed. Meredith did not address the issue, and instead focused her energies on Cristina's wedding, leaving her relationship with Derek uncertain. After Burke left Cristina at the altar, Meredith made an announcement to the guests that seemed to imply she had given up on her relationship with Derek as well: "It's over … so over." When Meredith asked her intern to call all four of Derek's sisters to ask for a donor nerve, it is revealed that Nancy still refuses to speak to her and hung up on her.

Kathleen Shepherd
Kathleen is Derek's older sister. Not much is known about their relationship.

Amelia Shepherd
Amelia is Derek's youngest sister. When she was younger, she stole her brother's prescription pad and overdosed. When Derek found her, she was out cold. He performed CPR for a while until an ambulance arrived. She was clinically dead for 3 whole minutes, but was able to be resuscitated. From then on the siblings drifted apart and became estranged.

When Derek got shot, Amelia went to Seattle to see him in hopes to restart their relationship. He didn't want her there and made comments on her past with drugs, but before she left for LA again, he talked to her on the hospital parking lot. For the first time, they talked about their father's death and the memories they shared. Derek said that he couldn't call her and tell her he was hurt because ever since their father had died, he had sworn to protect her. He didn't want her to know that pain even exists. They reconnected and their relationship was better ever since.

Amelia visited for a second time when she wanted him to help her with the brain tumor of Mason's mother, that was killing her. It was shortly after she got out of rehab again, so Derek told her she should give up on that impossible task because she was too fragile. Amelia didn't listen and practiced with Lexie to perform the surgery fast enough to not kill Erica right on the table. Finally, Derek gave in and agreed to help her because he was sure she would never give up. They later successfully performed the surgery and further bonded over the experience of giving a young boy his mother back.

Shortly before Cristina left, Amelia came once again to see her brother in Seattle, announcing she was now engaged to James. She decided to stay for a while, sometimes scrubbing in with Derek. She was seen having arguments with her fiancé and it turned out she wanted to stay permanently. Amelia became head of neurosurgery, taking Derek's job, because he wanted to leave for Washington anyway. Before he actually left, they fought a lot in the OR, both not dealing well with the reversed situation of her being his boss. It even came down to him being unclear to Owen about her drug history, so that she almost got fired. He apologized, admitting he wanted his job back.

When he eventually returned from DC, he didn't fight his little sister anymore. Derek was okay with taking her orders but Amelia was still suspicious, as she was convinced he wanted his old job back. Their relationship was better than ever despite him only being "second place".

One night, they had a conversation about their father again, as they had lost two men who were shot that day. Derek checked on Amelia to make sure she was okay. They sat down and talked about things, her eventually admitting that she was falling in love with Owen. And that she was scared. He reassured her and was totally okay with the idea of her and Owen.

On the car on his way to DC, before he had the accident, Derek had a call with Amelia. She was doing surgery on a car crash victim with April and Bailey and they talked about him not making it to his flight. The reception got bad and the last thing he said to her was "Amy, are you there?". It would be the last thing Amelia would ever hear her brother say as he died shortly after.

She struggled in the aftermath of Derek's death and would crack morbid jokes about him. Her grudge against Dr. Penelope Blake over her brother's wrongful death drew a wedge between her and her sister-in-law. Meredith wanted to move on and teach Dr. Blake to learn from her mistakes, while Amelia was still vengeful and mistreated her.

Carolyn Shepherd
His mother came to see him and meet Meredith. To begin with Meredith was nervous and attempted to be the bubbly happy 'Izzie-like' girl that mothers love, including a high ponytail complete with scrunchie. However after talking with the true Meredith for only a short while, she told Derek that she was the "good one" and gave him the ring his father wanted him to have for the "one". After accepting the ring, he began to plan a proposal to Meredith but worried that she still might not be ready. But when she mentioned their own future children in passing, he knew that she was ready for marriage. He told Mark he was going to propose, who told Richard Webber, Owen Hunt, and Callie Torres, but kept it secret from Meredith. Everyone suggested a grand proposal so he planned an elaborate one involving roses and a giant teddy bear. However an emergency call from Addison meant he had to abandon the proposal. After the death of Jen Harmon (a death he blamed himself for) and learning that he had lost more patients than those he had saved, he became depressed and returned to his trailer after lounging on the couch for several days. He began to drink a large amount and refused to return to work.

Richard informed Meredith about Derek's intention to propose and the ring leading to her going to confront Derek at the trailer. He pushed her away saying that she is "a lemon" and that she has just been waiting to get him out of the house. She tells him that she knows about the ring and he shows it to her before batting it into the woods and telling her to go. After being chastised by Richard, Meredith went to see Derek again. Derek asks her whether she would still love him if he wasn't a Dr. Meredith answers no, explaining that Izzie has cancer that has spread to her brain and he is one of only 20 people in the world who could save her. She couldn't love him if he wouldn't help her. Derek returned to the house and attempted to propose to Meredith but she refused him. He started work again, operating on Izzie. Just before the surgery, Meredith showed up with his ferryboat scrub cap and he asked her to marry him again but she turned him down.

At the end of her shift she was waiting for an elevator. After being guided by the chief to the right one, she found a clean-shaven Derek waiting for her. The elevator was decorated with scans of all the surgeries they did together. He recounted the stages of their relationships as they played out during each case. Lastly, he showed her the post-op scans of the different lives they have saved over the years, and, of course, Izzie's brain. "You got me into the OR," he told her. "If there is a crisis, you don't freeze, you move forward. You put the rest of us to move forward because you've seen worse, you've survived worse, and you know we'll survive too. You say you're all dark and twisty; it's not a flaw, it's a strength. It makes you who you are. I'm not gonna get down on one knee, I'm not gonna ask a question. I love you Meredith Grey, and I want to spend the rest of my life with you." She told him that she wanted to spend the rest of her life with him and they kissed.

As Izzie received treatment for her cancer, Meredith allowed her to plan the wedding for Derek and herself, in which Izzie took great joy in. However, on said wedding day, Izzie began to see Denny again and Bailey and Derek looked into the cause of this hallucination. They discovered another tumor, too small to be seen normally and too small for Derek to operate safely on. With the news of Izzie dying and her previous comments about spending her life with Alex, Derek and Meredith decided to give their wedding to Izzie to give her the happiest day of her life. Meredith and Derek intended to get married at city hall but found they had no time due to Izzie's surgery and the John Doe patient. So they chose to get married by writing their vows on a post-it note. They stated that they'd love each other, even when they hated each other; that they would never walk away and that they would care for each other when they were old, senile and smelly. The John Doe patient turned out to be their friend George.

Even with their fellow colleagues arguing the two were not actually married, Meredith and Derek viewed themselves as married. They consummated their marriage everywhere, including the kitchen and stairs, and referred to themselves as married. When Meredith chose to donate part of her liver to Thatcher, Derek demanded to be allowed in the OR, stating, "that's my wife you're cutting into." Eventually, they married each other legally, as it facilitated them adopting Zola.

Later, Meredith gave birth to a baby boy named Derek Bailey Shepherd, to be called "Bailey" after Miranda Bailey.

Career
Professionally, Derek is regarded one of the best neurosurgeons in the world. His services result in two million dollars worth of annual revenue for the hospital. He is a "tumor junkie" and has performed numerous complicated, risky procedures, including a stand-still operation, two double-barrel brain bypasses, and separation surgery for adult conjoined twins. One of his colleagues and patients Isaac once commented that the reason he came to Derek to take his spinal tumor out was because Derek, upon seeing his scans, was inspired rather than defeated. His confidence was shaken slightly when his surgery to repair a gunshot injury on a colleague, Preston Burke, resulted in Burke’s hand developing a tremor, but Derek remains a competent and skilled surgeon who has not forgotten the importance of compassion and bedside manner when dealing with patients. He is liked by his patients and their family members as he has a way of putting them at ease.

Derek's professional life hit an obstacle when Richard Webber announced his plans to retire. Derek had originally been promised the chief position when Richard offered him the job in Seattle, but was surprised to find that the position had instead been offered to Preston Burke. When word got out about Richard's retirement, Addison and Mark joined in the race for chief. Eventually, Webber came to a decision. He offered the Chief position to Derek, but Derek declined it and instead encouraged Richard to stay on as Chief.

Derek's confidence took another blow when he accidentally clipped an aneurysm on a pregnant woman during surgery, remarking that it was unlike him. While Addison is in Seattle tending to her brother, she consults, and Derek suggests a risky procedure, despite knowing nothing of the procedure or its risks, feeling immensely guilty over clipping the aneurysm and will do all in his, or Addison's, power to keep her alive. Unfortunately, she dies later in surgery, upsetting her husband, who calls Derek a murderer in his grief. This sends Derek into a depression. Later, at a deposition, he learns more of his patients have died than survived, which Meredith reasoned was because he often took seriously ill patients who were at their wits' end and had come to him because no other surgeon would operate on them. Nonetheless, he walks out of Seattle Grace.

While in his depression, pushing Meredith away and being almost constantly drunk, Bailey sends Callie and later Owen to try and bring him back. Derek, however, talks to both of them and makes them feel depressed over those who they have "killed", prompting them to start drinking with him, until Richard comes and shouts at him, telling him he is in a much better position than he was. He is promoted to Acting Chief of Surgery, after the Richard is forced into rehab to keep his job. After Derek orders a patient to be taken off life support against her husband's wishes, the husband returns to the hospital and searches for Derek, shooting several surgeons on his way to him. The shooter eventually finds Derek and shoots him, forcing Richard to take over as interim Chief during Derek's absence from work. Derek returns and immediately quits as Chief, admitting that he hates the job and just wants to go back to being a neurosurgeon. He later tells the counsellor that he had wanted to quit for a long time and the shooting prompted him to finally make the decision.

Over the course of his career, Derek has been the lead surgeon on two clinical trials. The first was initiated by Meredith—publicized as "The Shepherd Method", it is the injection of a live virus into a brain tumor as treatment. The second clinical trial was for the development of a cure for Alzheimer's, which he was able to fund through his earned Phillip's Grant. Derek was then blacklisted by the FDA after it was revealed that the trial was tampered with. The trial was carried on by Carl Baumann in Phoenix.

After the plane crash, Derek wasn't able to perform surgery for a while. During this time, he was teaching residents and helping Callie Torres with her trial on better prosthetics. The work on this trial led him to the development of brain sensors, which caught the attention of the president of the United States. The president requested him for a brain mapping project and gave him the opportunity to run it.

Notes and Trivia

 * He played saxophone in his high school band. He also plays guitar.
 * He has a scar on his forehead from a motorcycle accident.
 * He had a thing for ferry boats.
 * He was often seen as extremely protective over his sisters, especially Amelia.
 * Derek had five kinds of scrub caps, his favorite of which depicts ferry boats.
 * He had a high risk for liver cancer, prostate cancer, baldness, and heroin addiction.
 * In season one, Derek's lab coat did not show the post-nominal letters of F.A.C.S.
 * In Almost Grown and These Arms of Mine, there are scenes that show Derek wearing his "Chief of Surgery" lab coat, despite no longer holding the position at the time.
 * In Flight, Cristina tries to keep everyone conscious, but it's shown that Derek is asleep and dreaming about ferryboats, as his response to Cristina is "boats".
 * Before surgery, Derek often said "It's a beautiful day to save lives, people. Let's have some fun."
 * In Save Me, Derek revealed to Meredith lots of things because he hadn't opened up, My mother's maiden name, Maloney. I have four sisters. I have, uh, nine nieces. Five nephews. I like coffee ice cream, single-malt scotch, occasionally a good cigar. I like to fly fish. And I cheat when I do the crossword puzzle on Sunday. And I never dance in public. Um, favorite novel, The Sun Also Rises. Favorite band, The Clash. My favorite color is blue. I don't like light blue, indigo. The scar right here on my forehead, that's why I don't ride motorcycles anymore. And I live in that trailer. All this land is mine. I have no idea what I'm gonna do with it. So that's it. That's all you've earned for now. The rest you're just...just gonna have to take on faith.
 * Derek claims he never understood Cristina and Dr. Burke's relationship.
 * In Here Comes the Flood, Derek mentions that he is a pain specialist. In subsequent seasons he is shown to be a "tumor junkie" who takes on difficult brain or spinal tumors.
 * For Swedish viewers, he is known as Dr. Drömprins, meaning Dr. Dreamprince.
 * He missed his father every second of every minute of every day.
 * His father was never mentioned until Wish You Were Here.
 * His father used to own a shop.
 * Derek's ID badge stated his department was surgery until the merger with Seattle Grace Mercy West Hospital, and then it was updated to state his department as neurosurgery, although there were some scenes that still show his department as surgery.
 * He thought that chewing gum while performing an autopsy is disgusting.
 * In a sense, Derek often rooted for the underdog. He mentored both April Kepner and Heather Brooks, who at the time he mentored them were not very popular at the hospital.
 * He liked to have 16 towels in the O.R. Meredith reveals that it was to support his arms.
 * Derek's last thought was, "It's too late".
 * Derek was one of the "Grey Sloan Seven".
 * Derek was one of the "Seattle Grace Five".
 * He walked all his sisters except Amelia down the aisle on their wedding days.
 * He made $2,000,000 per year.

Notable Episodes
These episodes are Derek-centeric or otherwise very informative about his life.
 * Save Me
 * Who's Zoomin' Who?
 * Give Peace a Chance
 * Flight
 * Going, Going, Gone
 * Only Mama Knows
 * How to Save a Life

Memorable Quotes

 * (to Meredith) If there's a crisis, you don't freeze, you move forward. You get the rest of us to move forward. Because you've seen worse, you've survived worse, and you know we'll survive, too. You say you're all dark and twisty. It's not a flaw; it's a strength. It makes you who you are. I'm not gonna get down on one knee. I'm not gonna ask a question. I love you, Meredith Grey, and I want to spend the rest of my life with you.


 * (to Meredith) I am your knight in shining whatever.


 * (to Meredith)  I am calling post-it, Zola, Bailey, the tumors on the wall, ferryboat scrub caps. I thought D.C. was everything. I was wrong. You... you're everything. I love you and I'm not going to stop loving you. I can't live without you. I don't want to live without you, and I'm going to do everything in my power to prove it.


 * Meredith is the best mother a child could have. She loves Zola and she loves me, and if she has any flaws, it's that she loves people so much she will do anything for them.


 * (to Richard) Breakthroughs don't happen because of the medicine. Real breakthroughs happen because someone is scared to death to stop trying.


 * [narrating] Yes or no. In or out. Up or down. Live or die. Hero or coward. Fight or give in. I'll say it again to make sure you hear me. The human life is made up of choices. Live or die. That's the important choice. And it's not always in our hands.


 * Trust is hard for surgeons. We're trained from day one to believe that the only person we can trust is ourselves.


 * That's how you stay alive. When it hurts so much you can't breathe, that's how you survive. By remembering that one day, somehow impossibly, you won't feel this way. I won't hurt this much.


 * You're the love of my life. I can't leave you. But you're constantly leaving me.


 * We have survived an unusual number of bad things.


 * (to Ellis) You broke her. You called her ordinary. You told her time and time again that nothing she does is ever good enough. Every good thing Meredith has done is despite you. She may not survive this. That's on you. That is on you!


 * Life is short. So now I think less and just do.


 * (to Addison) There was a time I thought you were the love of my life. Things change.


 * Don't McDreamy me!


 * (to Richard) I loved her enough to walk away.


 * (to Meredith) I wanna marry you. I wanna have kids with you. I wanna build us a house. I wanna settle down and grow old with you. I want to die when I'm 110 years old in your arms. I don't want 48 uninterrupted hours. I want a lifetime.


 * We can talk about our feelings. It's just that most of the time we'd really rather not.


 * I am a human being, I make mistakes. I'm flawed. We all are.


 * Here's the truth about the truth. It hurts. So we lie. We lie to ourselves because the truth freaking hurts.


 * Derek: I'm not gonna die, I promise.
 * Meredith: Good, because that would be the worst breakup ever.


 * You can expect that I'm gonna show up, even if I yell, even if you yell, I'm always gonna show up.


 * I'm someone you need to get to know to love.


 * Stay here. Don't move. Wait for me.


 * Meredith: - You're sexually harassing me!
 * Derek: I'm riding an elevator.


 * It was the first surgery we ever scrubbed in together on. Our first save. Right here is a cerebral cyst. Tough save, but we did it. I kissed you in the stairwell after the surgery. And this right here is where Dr. Bailey kicked you out of the surgery, because she caught us in your driveway, in my car. And right here, this is a seven hour craniotomy. You held the clamp the entire time, never flinched. That's when I knew you were gonna be an incredible surgeon. Beth Monroe, made our clinical trial a success by surviving. You talked me into putting her under. That's when I knew I needed you. And this is today, post op head CT of Izzie Stevens. You see that? Right there. Tumor free. Because of you. You got me into the OR. If there's a crisis, you don't freeze, you move forward. You get the rest of us to move forward. Because you've seen worse. You've survived worse, and you know we'll survive too. You say you're all dark and twisty. It's not a flaw, it's a strength. It makes you who you are. I'm not gonna get down on one knee, I'm not gonna ask a question. I love you Meredith Grey, and I wanna spend the rest of my life, with you.

Appearances
Derek Shepherd Derek Shepherd Derek Shepherd