The Vampire Diaries Universe may have come to a (seemingly temporary) end with the Legacies finale, but the love and adoration for bad boy Damon Salvatore remains as strong as ever. Damon's appeal lay in his role of being the perfect antihero and the redemption arc that he went through after he got together with his lady love Elena.
However, before becoming a likable character, Damon made some questionable decisions and choices. It's easy to forget that he was cruel, harsh and absolutely ruthless when he had to be, especially in the earlier seasons of The Vampire Diaries.
Made Elena Turn Her Humanity Off
One of Jeremy's more permanent deaths was Elena's undoing. Damon tried to help her in the worst way possible: by telling her to flip off her humanity switch in order to deal with the tidal wave of grief that overwhelmed her.
This was a terrible piece of advice to give since Elena was a new vampire, filled with bloodlust (more than an older vampire) and nobody could have predicted what she would have done. She burnt down her brother's body in her parents' home, which she regretted a lot later on.
Crashed Into The Grill To Make It To The Other Side
The plans to foil villains on TVD could get quite elaborate and farfetched, and Damon's plot to kill the Travelers by crashing into the Mystic Grill in his car was the most ridiculous. Not only did he kill himself but also Elena, and he depended on a fragile Other Side and an overworked Bennett witch to bring him back to life.
The worst-case scenario happened, and he and Bonnie got stuck in a Prison World with Kai, who did unspeakable things to the gang once he made it out.
Snapped Jeremy's Neck In Front Of Elena
As a character, Damon was unpredictable and impulsive, especially in season 2. He was weak-willed and couldn't handle the simplest rejection from Elena, which led him to drop all restraints and snap her brother's neck, right in front of her.
This was an unforgivable act by the elder Salvatore, and he stayed on everyone's bad side for a while after doing so. Ultimately love won over and Elena forgave him, but his decision to kill his crush's brother would not fly in today's day and age.
Forced Elena To Drink His Blood
Respecting boundaries and ethics was never Damon's strong suit, so it was no surprise that he overstepped his bounds by imposing his will upon Elena. Her choices meant nothing to him, and he seemed to think he knew what was best for her.
When Elena's life was threatened by Klaus, he forced her to feed on his blood, which meant that if she died, she would be reborn as a vampire, which was a fate that Elena hated to have thrust upon her.
Abandoned Enzo In The Fire
For the most part, friendship was never Damon's cup of tea, yet he made some unlikely pals along the way. Trapped as an Augustine vampire, the only person who helped him keep it together was Enzo, and it was with Enzo's sacrifice that Damon was able to get strong enough to overcome the society.
Still, when it came to his life or Enzo's, Damon chose to leave his only friend in a burning cage, and ran away by turning off his humanity switch so that he didn't even feel remorse for his actions.
Refused To Transfer The Mark From Stefan
Stefan was wronged by both Valerie and Damon, who knew how to lighten his load by transferring Rayna's mark from the Phoenix sword to a family member. However, though Damon first volunteered, he then refused to take on the cursed scar for his brother, which was a great betrayal.
Stefan had given up his life and happiness countless times, like going Ripper with Klaus, to save Damon's life, but the one time he had to reciprocate the favor, it took him two tries to do it.
Fell For Katherine's Seductions
Damon fell for Katherine's charms not once, but twice. In 1864, he was enchanted by her beauty and vampiric nature, so he dedicated his heart and soul to her, but she only used the brothers as her getaway car and let them get shot, and thus turn into vampires.
Despite this, Damn waited almost a century to bring Katherine out of the tomb that she wasn't in, and he thirsted for her love. When she finally did meet him, he again gave in to his feelings and she only hurt him by telling him she never loved him.
Turned Bonnie's Mother Into A Vampire
Bonnie and Damon had a long and complicated story, but when they hated each other, Damon went ahead and traumatized her by turning her mother into a vampire so that Esther could stop channeling Bennett witch power from the women.
Bonnie was a cooperative and helpful friend, who always went out of her way to make life better for her friends. Therefore, it was extremely unfair to take one of her few family members, especially after she had just connected with her, and make her supernatural.
Killed Sarah Salvatore's Mother
Murder was a part of Damon's life, but slaughtering a pregnant woman was not his finest moment. His victim was Zach Salvatore's partner, pregnant with the next in the Salvatore line, and Damon thought it was acceptable to kill a lady with child.
He would have also killed the baby, Sarah, had Stefan not rescued her and given her a good life. Until the time Sarah was protected, she was fine, but being exposed to Damon led to her demise too.
Used Lexi As Bait
Few other things rankle as much as Damon's trickery with Lexi. Stefan's best friend was a spunky, fun vampire who audiences loved. Just as fans were getting to know her, Damon used Lexi as bait in his ploy to pretend he wasn't a vampire, so that he could get on the Founder's Council.
So, Damon staked her in the heart as he looked her in the eye, and ended her undead life to make himself look like a trustworthy ally. This alienated him from his brother and Lexi fans equally.