Damon's 5 Most Evil Moments On 'TVD'

Damon Salvatore has always been something of an antihero, emphasis on the anti. He's the bad boy Salvatore brother. He's the dark to Stefan's light. He's amazingly sexy but with a bit of a sadistic streak. In Thursday's "Man on Fire," yet more of Damon's dark past came to light — but not for him. We already know that he left his BFF Enzo for dead and then turned off his humanity to cope, but it turns out he wronged Enzo in another big way: He killed the love of his life, Maggie.

Damon lives (or, you know, whatever vampires do) in shades of gray and Maggie's death proved it. Did Damon kill her? Yes. Absolutely. But it was self-defense and he had (to this day) no idea who she was to Enzo. Stefan and Elena are keeping the dirty deed a secret from Damon for now, but he has to figure it out sooner or later… especially since Enzo died at Stefan's hands tonight and seems pretty set on haunting his old buddy.

In honor of Damon's unshakable bad behavior, let's look back on five of his most diabolical, evil and just plain cringeworthy moments over the years.

5. Torturing Mason Lockwood.

Poor Tyler Lockwood. No one who loves him (and isn't named Caroline) is allowed to live. One of Damon's early acts of torture was directed at Mason Lockwood, Tyler's uncle who tells him about the Lockwood curse. Damon's acts of torture are never easy to watch, but Mason really gets put through the ringer. Gag.

4. Abandoning Enzo.

This one sets off a whole chain of evil and bad news bears for everyone involved. After bonding for years as prisoners in the Augustine experiments, Damon and Enzo work together on a plan to escape. It's Enzo's plan and Damon only gets to run lead on it out of luck. Then, when the time comes, Enzo is too weak to help himself escape and Damon has to choose between a sure thing to get himself out or risking it all to help Enzo escape too – but risking death or recapture to do so. Damon turns off his emotions and bolts, leaving Enzo for dead (if only he had, you know, actually died).

3. Killing Aaron Whitmore.

When Elena dumps him in Season 5, Damon takes a big leap back to the dark side, joining his old buddy/current frenemy Enzo on a refreshing killing spree that starts with Aaron Whitmore. They stage a car accident, lure the kind-hearted and helpful Aaron out into danger and then brutally murder him. Elena would not be pleased, Damon.

2. Killing Jeremy Gilbert.

Yeah, this is pretty much the worst and it's hard to believe Elena even forgave him for it. Luckily, Jeremy is virtually unkillable, which is impressive since he's one of the few characters on the show who isn't officially immortal.

1. Staking Lexi.

Sorry, Jere, but this is the worst one by far. It still pains me to think of Lexi's death. And her reappearances in flashbacks and ghosty episodes have been some of the best moments of the show. Caroline and Stefan are cute platonic besties, but they don't hold a candle to the awesomeness of Lexi and Stefan. She was gone far, far too soon. RIP, Lex.

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