1. Mary Portman

Mary was a long-time patient of Bailey's. She survived the hospital shooting by playing dead and proceeded to help Bailey take care of Charles Percy in his final moments. And then Shonda Rhimes kills her; she let her survive all that and then she just kills her off without an explanation.

2. Henry Burton

We all should have seen this coming; he had a chronic tumor condition. That didn't make it any less painful when he was ripped from our lives. The fact that Christina was the one operating made it 100x worse.

3. Denny Duquette

Watching Izzy lose the love of her life was one of the hardest parts of the show to watch. Denny was an amazing character; seeing Izzy cling to his lifeless body was gut-wrenching. And then, Shonda brings him back, but only so that he could be Izzy's angel of death; it was a true tragedy.

4. Jimmy Evans

Alex's father was made out to be terrible when he stumbles into the ER and reunites with Alex, it makes his death so much worse. And to add insult to injury the reason he died was because Shane had a meltdown while operating. This led to a lot of unresolved emotional issues for Alex and a tragic death for his father.

5. Francesca "Frankie" McNeil

Frankie is from a family that came into the hospital thinking they needed a heart transplant for one child and found out they also needed it for another. But of course Shonda Rhimes has to make it difficult and there can only be one heart and Christina Yang has to choose which kid gets it. She gave it to the child she thought had the best chance at surviving and even though she tried to help Frankie, it was futile. This scene left everyone in tears.

6. Tommy Peterson

Tommy Peterson was born 3 months too early which resulted in his being put in the NICU. His premature birth caused many complications, and after a few weeks he died in the arms of his mother while Alex disconnected the machines that had been keeping him alive. All Grey's deaths are terrible, but the death of a baby was worse than any other.

7. Harold O'Malley

Harold O'Malley was brought into the hospital for a broken clavicle and treated by Callie, but when he complained of stomach pains, it was discovered that he had cancer which had spread to just about everywhere. After awhile, Harold eventually died from multiple organ failure while in the presence of his family. Watching him get taken off of life support and slowly die in front of his children was one of the saddest moments.

8. Susan Grey

While compared to most deaths, this one was not nearly as tragic as many others. What made it so terrifying was that she died from something most of us experience quite often. She died from the freaking hiccups.

9. Jen Harmon

Jen Harmon's death was perhaps one of the more unexpected ones; she originally came in because she ran over her husband's foot only to collapse on arrival at the hospital. Turns out her pregnancy was causing her issues and she had an aneurysm--which Derek of course fixed--and then she was in the clear. Or so we thought because shortly after that, she went back into surgery and Derek proceeds to remove most of her brain in an attempt to save her, but only the baby survives which makes it all the more devastating.

10. Bonnie Crasnoff

No one can forget this episode in which two people were impaled onto a pole in the wake of a train crash; one of them being Bonnie Crasnoff. Her and a man were both stuck on the pole and after assessing the situation, it was determined that he was more likely to survive the removal and therefore she asked Derek to tell her fiancé goodbye for her. When they removed the pole in the OR, the doctors abandoned Bonnie to work on the man because he had a better chance at living; except Meredith Grey. She only stopped CPR when Bailey called time of death and forced her to--it was a horrific scene.

11. Jessica Smithson

There is nothing worse than when a show kills off a child--it doesn't happen a lot in Grey's but when it does it is terrible. Jessica was a young girl who had Tay-Sachs and at the age of 6 she was nearing the end of her time; her father brought her to the hospital and was insisting they needed more time so he could get her to Mexico for an experimental treatment. Jessica's dad was stuck in a delusional state in which he thought they still could go to Mexico and so Bailey acted as the main form of comfort for Jessica. Bailey layed with Jessica and rocked her like she does with her own son until her father realized this was it and took over.

12. Madeleine Skurski

Madeleine thought she had the stomach flu--to her surprise it turned out to be a wide-spread cancer that was incurable at this stage. Madeleine was a math teacher and upon her diagnosis, her primary concern was not herself, but how she would break the news to her students. Her devotion to her students made her death all the more heartbreaking because it clearly affected them.

13. Emile Flores

Emile was admitted to the hospital after the roof of the restaurant he worked at collapsed on Valentine's Day. He bribed Karev to put him next to another patient--Mrs. Banks. Emile discloses to Karev that he had fallen in love with Mrs. Banks years ago when she had started coming to the restaurant, and then she had started to bring her future husband with her. Emile had never told her his true feelings, but she happened to overhear when he told Karev which was good because Emile died shortly after. Unrequited love and death are two things that when paired together are a recipe for tragedy.