8 of Tristan Thompson's Cheating Scandals and Flirtationships – From Khloé Kardashian to Sydney Chase

Tristan Thompson started appearing in headlines left and right when he began dating Khloé Kardashian in 2016. Criticism soon emerged as fans noticed that their relationship overlapped with Thompson's past romance with Jordan Craig, who he reportedly left for the Keeping Up With the Kardashians star while she was pregnant with their child.

As rumors still bombarded his relationship with Kardashian, he dismissed the claims in July 2019 and clarified that they were both single when they met.

"The negative comments that are constantly being directed toward her are unnecessary," he said in a tweet. "She does not deserve all this backlash for my wrongdoings. Both Khloè and Jordan have been nothing but great mothers to my kids."

Kardashian also addressed the speculations in a separate social media post in which she disclosed that they met after the NBA star chose to go on a blind date with her.

TMZ released the October 2017 footage it obtained showing Thompson kissing two women at a Washington, D.C., hookah lounge. The incident was only made public in April 2018 while he was dealing with another cheating scandal involving Lani Blair.

Amid the hookah lounge scandal, Thompson found himself in another cheating scandal while he was with Kardashian when the Daily Mail released video footage taken during his night out at the PH-D Rooftop Bar. The clip also captured him seemingly kissing Blair.

Page Six soon released photographs of the strip club worker arriving at Thompson's hotel room.

Kylie Jenner's "former" best friend Jordyn Woods became part of Thompson's cheating spree when they were caught kissing at a house party.

Woods addressed the issue on the March 1, 2019, episode of Red Table Talk, saying she should have gone home after the party.

"Never once was I giving him a lap dance, making out with him, sitting all over him," she said. "It's just we're all together; we're in a group. Never once did we leave the public area, go to the bedroom, go to the bathroom ... I was drunk. I was not tipsy – I was drunk."

She admitted that they did kiss at one point but clarified it had no "passion."

Thompson and Woods broke up after the cheating scandal was made public.

Due to his past cheating controversies, Thompson failed to control everything when he was slammed after having a night out with a mystery blonde in Texas.

TMZ soon clarified that the woman was his manager Julia, and the outing was nothing special.

Thompson faced one of his biggest scandals yet when Maralee Nichols sued him over the paternity of their then-newborn son, but the Cleveland Cavaliers player hit back with his own documents saying that their relationship was only based on s--.

"I met Tristan in 2020 at a party at his home in Encino, California. He told me he was single and co-parenting," Nichols told Us Weekly. "I would never have gotten involved with Tristan if I thought he was in a relationship."

She insisted that she had no idea that Thompson and Kardashian were back together.

In 2021, Thompson was linked to Sydney Chase, who claimed they hooked up earlier that year.

"He told me he was not in a relationship anymore, so I said OK," she told the "No Jumper" podcast. "We talked, we hung out multiple times, we went out together, everything."

The father of four sent a cease-and-desist document, alleging that the Instagram model made "false and defamatory statements."

After laying low, Thompson was spotted hugging a new mystery blonde woman outside the Universal Appliance and Kitchen Center. No further details were released afterward.