Grey’s Anatomy’s All-Time Saddest Deaths: It’s Tears for Years on the 10th Anniversary of McDreamy’s Passing

When we tuned into the “How to Save a Life” episode of Grey’s Anatomy on April 23, 2015, we had no idea what we were in for, no clue that original cast member Patrick Dempsey was going to be killed off as Dr. Derek Shepherd after 11 seasons. (The actor still had a year left to go on his contract.) But even if we had been forewarned, we still wouldn’t have been adequately forearmed against the emotional roller-coaster ride that the hour held in store.

One minute, it appeared that McDreamy was going be fine, just fine. Maybe rumors of his imminent death had been greatly exaggerated, we wishfully thought. Maybe it was all but a classic Grey’s Anatomy misdirect. But then the next minute, the neurosurgeon’s car had been rammed into by an 18-wheeler, and Meredith Grey’s beloved husband had been rushed to a subpar hospital where he’d subsequently perish.

We, along with Mer and everyone who adored Derek, were gutted. Behind the scenes, however, it wasn’t necessarily such a sad occasion. In Lynette Rice’s How to Save a Life: The Inside Story of Grey’s Anatomy, former executive producer James D. Parriott said that “there were HR issues” with Dempsey. “It wasn’t sexual in any way. He sort of was terrorizing the set. 

“Some cast members had all sorts of PTSD with him,” he added. “He had this hold on the set where he knew he could stop production and scare people.”

Perhaps the actor’s departure was the silver lining to the dark cloud that was the demise of his popular character. (Dempsey reprised his role in Season 17 when a comatose Mer encountered her late spouse on what fans dubbed her “COVID beach.”) On the anniversary of Derek’s passing, scroll through the below ranking of the long-running drama’s most impactful deaths.

25

Jessica Smithson

greys jessica smithson

Photo : ABC screenshot

We still get a lump in our throats just thinking about the little girl whose father was desperate to get her to Mexico for an experimental treatment to save her life. When Bailey finally forced him to hold his daughter as she slipped away, we damn near died along with her.

24

Bonnie Crasnoff

greys bonnie crasnoff

Photo : ABC screenshot

When the pole connecting this Season 2 patient to fellow train-crash victim Tom Maynard was removed, making the hospital her last stop, we were the real wrecks. And don’t even get us started on the bittersweet message that she had Derek deliver to her fianc… Too late. Sniffle.

23

Mary Portman

greys mandy moore

Photo : ABC screenshot

Though the patient that This Is Us’ Mandy Moore played made it through Gary Clark’s Season 6 shooting spree unscathed, she stunned her husband, Bailey and us along with them when she simply didn’t wake up after routine colostomy bag reversal surgery the following season.

22

Reed Adamson

greys reed

Photo : ABC screenshot

Speaking of Gary Clark’s reign of terror, this Mercy West transplant had no sooner made the mistake of telling him that she was a surgeon, not a tour guide, than he’d put a bullet in her head and left her body behind to be found by bestie April.

21

Olive Warner

greys olive mary kay place

Photo : ABC screenshot

Richard’s Alcoholics Anonymous sponsor had accepted her imminent demise and was ready to go in Season 14. Trouble was, Richard wasn’t ready to let go of his dear friend, played by Mary Kay Place — and neither were we, it turned out.

20

Chloe Yasuda

Rude Awakening (Season 21, Episode 7)
We were as devastated as Mika when she regained consciousness following a devastating car wreck with her cancer-stricken sister, only to be informed by Bailey’s stricken expression that Chloe hadn’t survived.

Photo : ABC screenshot

Mika’s beloved kid sister had just endured her first round of chemo in Season 21 when a car accident with her drowsy sib left her with injuries from which she wouldn’t recover. And as sad as that was, Mika’s reaction upon learning that Chloe hadn’t pulled through — see above — was even sadder.

19

Kyle Diaz

greys kyle wilmer valderrama

Photo : ABC screenshot

“Faster, Jo! Faster!” we cried. But alas, she didn’t get to the gallery in time to keep Stephanie from seeing as her musician boyfriend, played during Season 12 by Wilmer Valderrama, passed away on the operating table and was pronounced dead by Amelia.

18

Susan Grey

greys mare winningham

Photo : ABC screenshot

Sure, we felt bad for Thatcher when he lost his second wife during Season 3 of what started as just a case of chronic hiccups. But we felt a hell of a lot worse for Meredith when she told him that Mare Winningham’s sweet character had passed, and in response, he slapped his daughter.

17

Heather Brooks

tina majorino greys

Photo : Courtesy of ABC

We still wish that Tina Majorino’s Season 10 exit hadn’t been so “shocking”: If the erstwhile “Mousey” hadn’t been electrocuted following a superstorm, by now the actress might have returned to slip into the lab coat that had accidentally been made for Heather despite the fact that she never got to complete her internship.

16

Elena Bailey

bailey mom elena greys

Photo : ABC screenshot

We’ll never listen to “My Girl” the same way again — not after hearing the tear-stained rendition of The Temptations’ classic that Bailey sang to her beloved mother in Season 17 as she lay dying of COVID.

15

Dylan Young

kyle chandler dylan greys

Photo : ABC screenshot

It was with red eyes and heavy hearts that we watched in horror as Kyle Chandler’s Bomb Squad Guy was blown to bits during Season 2 after calming down Meredith enough to remove an explosive device from a patient.

14

Craig Thomas

greys william daniels

Photo : ABC screenshot

Though Cristina argued endlessly with her old-fashioned Mayo Clinic mentor, played by William Daniels, she came to care deeply for him. So when he suffered a heart attack while performing an operation during Season 9, we were as gutted as she was.

13

Diane Pierce

diane dies greys

Photo : ABC screenshot

We knew that Maggie’s adoptive mother was dying. Yet that did nada to lessen the blow when she stopped doling out life lessons (“Be a little slutty”) and quietly slipped away during Season 13 as her daughter was painting her nails.

12

Adele Webber

<h3>15. Richard and Adele</h3>
<p>Thanks to the Webbers, to this day, we can't hear "My Funny Valentine" without tearing up. Luckily, when it gets played a lot, there's usually chocolates around.</p>

Photo : Courtesy of ABC

Richard’s first wife died off screen during Season 9. However, Grey’s still made sure that we felt the full impact of his loss when the new widower pictured himself and his missus dancing to “My Funny Valentine” as he watched Bailey and Ben on the floor at their wedding.

11

Thatcher Grey

Photo : Courtesy of ABC

Before Mer’s estranged father died in hospice in Season 15, he made peace with her as best he could by thanking her for the gift of time that she’d given him along with part of her liver. “I just wish,” he added ruefully, “you and I could have shared it.”

10

Ellis Grey

Photo : ABC screenshot

After Meredith died in Season 3, she bumped into her mother in sort of a dimension between life and the afterlife. “You are anything but ordinary,” the elder Grey said before sending her daughter on a journey back to the other side — a journey she herself would never make.

09

Andrew DeLuca

Photo : ABC screenshot

Meredith spoke for us all in Season 17’s midseason premiere when she told her onetime significant other that she’d miss him if he stayed on the other side. But stay, he did. After being stabbed by a sex trafficker, he succumbed to his injuries and reunited in the afterlife with his beloved mother.

08

Doc

Photo : ABC screenshot

We were already in tears when Mer and Derek made the heartrending decision to put down their (and Addison’s) ailing dog in Season 2. But then Mer refused to let Finn dispose of him like garbage — instead, she and Derek would bury Doc near the trailer — and we completely lost it.

07

Samuel Norbert Avery

Photo : ABC screenshot

Lives don’t come much shorter or more painful than that of Jackson and April’s son. Owing to osteogenesis imperfecta, the baby’s bones began breaking in the womb during Season 11, so labor was induced at just 24 weeks. When the newborn died soon after, a part of his parents went with him.

06

Henry Burton

Photo : ABC screenshot

Teddy never meant to fall in love with Scott Foley’s patient; she only married him to get him on her insurance. But by the time he expired during a Season 8 tumor resection, not only was she crazy about him, so were we.

05

Denny Duquette Jr.

Photo : Courtesy of ABC

By the hardest, Jeffrey Dean Morgan’s charmer had gotten — and survived — his Season 2 heart transplant. He even had warm hands afterwards! But he’d no sooner gotten Izzie to say yes to his marriage proposal than he’d thrown a blood clot and given their romance the unhappiest of endings.

04

Lexie Grey

Photo : ABC screenshot

But… but… Lexie and Mark were supposed to get married and have kids. They were meant to be. She’d agreed with him on that. “Meant to be” was even the last thing she said… before succumbing to injuries sustained in the plane crash with which Season 8 ended.

03

Mark Sloan

Photo : ABC screenshot

Not cool, Grey’s. Not cool. The show let us think that McSteamy was gonna be OK after the plane crash, only to let him slip into a coma during Season 9 before being taken off life-support and leaving behind a crazy-hot corpse.

02

George O’Malley

Photo : ABC screenshot

We never saw it coming. In Season 5, George was on his way to become a trauma surgeon in the army when he leapt in front of a bus to save a woman. Afterwards, he was so unrecognizable that he might’ve died a John Doe, had he not traced a telltale 007 in the palm of Mer’s hand.

01

Derek Shepherd

Photo : ABC screenshot

After McDreamy spent a beautiful day saving lives during Season 11, his car was rammed by a semi, and Dillard Medical Center botched his treatment. “It’s OK,” Mer told her husband after he was taken off life-support. “You go. I’ll be fine.” And she was. But at the time, we weren’t sure we ever would be again.

Related Posts

The Newest Season of ‘Grey’s Anatomy’ Is Finally Coming to Netflix

If you don't own a Hulu subscription and were just waiting for the moment when Grey's Anatomy would finally become available on Netflix, you will be glad…

A Failed Backdoor Sitcom Pilot Helped Launch a Grey’s Anatomy Star’s Career

Before Eric Dane became known as the charismatic, handsome Dr. Mark Sloan (a.k.a. "McSteamy") in Grey's Anatomy, he got his start in a much humbler, short-lived TV…

Sandra Oh Reveals If She Watches Grey’s Anatomy Reruns 11 Years Since Cristina Yang Left The Show

Sandra Oh revealed whether she follows Grey's Anatomy after having played the key character Cristina Yang for 10 seasons. Oh left the medical drama at the end…

Sandra Oh Reveals Whether She Ever Watches Grey’s Anatomy Reruns

Don't expect Sandra Oh to be cuing up old episodes of Grey's Anatomy in her free time. The award-winning actress, who starred as the beloved Cristina Yang…

Grey’s Anatomy Season-Finale Recap: Explosions in the Sky

At this point, I should be immune to surprises when it comes to Grey’s Anatomy. I mean, this is the show that blew up Kyle Chandler in the…

‘Grey’s Anatomy’ Is Just So Bad Now

I bailed on Grey’s Anatomy for maybe 12 or 13 seasons, but I returned at the end of the 19th season and continued watching through seasons 20 and 21….