When Tristan Thompson first started dating Khloé Kardashian in 2016, he already had a reputation for being a player. In fact, it has been speculated that the athlete began seeing the reality star while he was still in a relationship with his ex-girlfriend, Jordan Craig, who was pregnant with their son at the time.
However, Khloé Kardashian and Tristan Thompson had since claimed that even though Jordan Craig was carrying his child, the athlete was single when they first started dating. Just two weeks after Khloé Kardashian announced she was expecting her first child, he was filmed with kissing two women at a hookah lounge outside of Washington, DC.
Though many thought Khloé Kardashian would have called it quits from Tristan Thompson right then and there, the pair’s relationship remained intact with the Good American founder eventually moving to Cleveland, where the athlete was playing basketball.
While it seemed like Tristan Thompson and Khloé Kardashian’s relationship was as solid as ever, things quickly went downhill when the footage of him getting cozy with the two women went public, just hours before the reality star was due to give birth to their child.
Even though the situation was rather messy, Khloé Kardashian seemingly overlooked her boyfriend’s slip-up and forgave him. But in February 2019, Tristan Thompson’s unfaithful ways proved to be the final straw for the reality star as she broke off their relationship for good after learning of his alleged hook up with Kylie Jenner’s former BFF Jordyn Woods.
Since his first cheating scandal caused a massive media storm, Kris Jenner decided to take matters into her own hands to ensure that Tristan Thompson would never cheat on her daughter again.
Following the birth of the former couple’s daughter, True, in April 2018, it was reported that the Kardashian matriarch made the athlete sign a contract requiring him to put $10 million in a trust fund for his new baby with Khloé Kardashian, whenever he was caught cheating moving forward.