All Of Tristan Thompson's Cheating Scandals, Explained

In Elite Daily’s It’s Complicated series, we dissect the biggest celebrity drama to find out what happened in front of the camera, behind the scenes, and everywhere in between. In this piece, we look at Tristan Thompson’s complicated relationship with infidelity.

Khloé Kardashian and Tristan Thompson's relationship has been an especially tumultuous one. Navigating romance as a celebrity is no easy feat, but Kardashian’s reality TV star status meant all of the pair's ups and downs played out on television as well as the internet. Unfortunately, many of the "downs" stemmed from reported (and some confirmed) infidelity on Thompson's part. The pair has gone from seemingly blissfully happy to broken up in a matter of hours on multiple occasions, and it seems Tristan's reported wandering eye is often the cause.

While the pair is currently broken up (reportedly due to infidelity), you never really know where these two could end up. Even in the face of Thompson’s transgressions and the public’s peering eyes, they’ve always found their way back to each other. For example, a few weeks after their June 2021 split, they were spotted at a birthday party for LeBron James’ wife, Savannah Brinson, on Aug. 28.

Despite Thompson’s less-than-stellar track record as a boyfriend, his track record as a dad is much more impressive. In spite of all the drama with Kardashian, he’s remained a constant presence in True’s life through the years. Regardless of what happens in the future, all of Tristan Thompson's cheating scandals are a lot to digest.

August 2016: Thompson Dates Khloé While His Ex, Jordan Craig, Is Pregnant

When Thompson started dating Kardashian in the summer of 2016, rumors flew that the relationship overlapped with Thompson’s relationship with Craig, who Thompson dated from 2014 to 2016. Seeing as Craig was pregnant with Thompson’s first child when Thompson and Kardashian first hit it off in August, fans assumed he was two-timing Craig with Kardashian. Craig gave birth to her and Thompson’s son, Prince, in December 2016, when Thompson and Kardashian were already four months into their relationship. However, Thompson insisted he never cheated on his pregnant ex and was fully single when he began dating Kardashian.

Thompson took to Twitter in July 2019 to clear up the rumors that had been festering for years. “When I met Khloe, I was SINGLE,” he told his followers on Twitter in a July 31, 2019, tweet. “The negative comments that are constantly being directed toward her are unnecessary. She does not deserve all this backlash for my wrongdoings. Both Khloè and Jordan have been nothing but great mothers to my kids.”

Even Kardashian spoke out about the matter, and her statement was aligned with Thompson’s. “My truth is: I met Tristan because HE CHOSE to go on a blind date with me. A mutual friend set us up. After going on some dates, Tristan told me that he had an ex that was pregnant,” Kardashian said in a lengthy post on her Instagram story. “Obviously, I was reluctant about us continuing to date or start a relationship,” she continued. “He pleaded with me that the relationship was over long before we met. He had me talk with his most inner circle. He showed me physical proof (correspondence between the two) and had me on calls with his lawyers to prove his point. His best friends, business associates, and even his mother told me, him and his ex were broken up before we met.”

As for Craig, she said the timing of Thompson’s new relationship was devastating. “Every day several articles were published worldwide mocking my new unfortunate reality and my pregnancy would now become one of the most popular gossip headlines due to the woman Tristan was now publicly dating during my pregnancy,” she said in court documents obtained by RadarOnline in June 2019, which claimed she faced pregnancy complications due to Thompson’s cheating. “Tristan insisted he would change for our family, and tried to get back together on numerous occasions," she added.

October 2017: The Hookah Lounge Incident

In 2018, TMZ obtained old surveillance footage of Thompson seemingly motorboating and kissing two women at a Washington D.C. hookah lounge. At the time the video was released (and when it was taken in 2017), Kardashian was pregnant with True, so it wasn’t the best look. The incident was made public in April 2018 around the same time another cheating scandal involving Instagram model Lani Blaire went viral. Thompson never addressed the footage from the Hookah Lounge directly. Elite Daily previously reached out to Kardashian and Thompson's teams for comment on the hookah lounge scandal.

April 2018: A Weekend With Lani Blaire

Thompson was caught up in another cheating scandal while dating Kardashian in April 2018 when the NBA star was spotted out with strip club worker Lani Blaire. In video footage obtained from a night out at the PH-D Rooftop Bar by the Daily Mail, they appeared to kiss. Later in the night, Page Six reported Blaire was seen arriving at Thompson’s hotel room at the Four Seasons.

According to Page Six, the pair spent the whole weekend together, also stopping at Soho House. At the time, Kardashian was about to give birth to True, so she understandably never addressed the situation on social media.

Blaire never directly addressed the situation either, but she did make it clear she wanted to put it in her past. As she told Us Weekly on her birthday in June 2018, "I’m not even thinking about that right now. I just want to go inside. Have a good time. Have a couple drinks."

February 2019: The Jordyn Woods Kiss

Undoubtedly the most talked-about of Thompson’s cheating scandals was his rendezvous with Jordyn Woods. Keeping Up With The Kardashians fans knew Woods as a longtime family friend to the KarJenners. While she was tight with all the sisters, she was ride-or-die besties with Kylie Jenner, so the discovery she and Thompson kissed at a house party in February 2019 was the ultimate betrayal.

Woods opened up about the night on Red Table Talk on March 1, explaining that she regretted putting herself in that situation. She explained,

I should have gone home after the party. I shouldn’t have even been there ... Never once was I giving him a lap dance, making out with him, sitting all over him. 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. But I was not beyond the point of recollection. I know where I was. But on the way out, he did kiss me ... No passion, no nothing.

The incident drove Woods and the KarJenners apart, and Khloé shaded Woods publicly online for not addressing the situation with her directly. “Why are you lying @jordynwoods??” she tweeted after Woods claimed on Red Table Talk that she wasn’t the reason for the couple’s split. “If you’re going to try and save yourself by going public, INSTEAD OF CALLING ME PRIVATELY TO APOLOGIZE FIRST, at least be HONEST about your story. BTW, You ARE the reason my family broke up!”

As for Thompson, he and Kardashian called it quits after the scandal broke, and he was exiled from the family for a time, but not forever. It was more than a year before they would reconcile in August 2020, but his kiss with Woods was discussed for much of 2019 and tainted public perception of their relationship even further. Thompson never directly addressed the cheating scandal with Woods. Elite Daily previously reached out to Thompson’s team for comment, but never heard back.

December 2020: A Mystery Blonde Mixup

In December 2020, Thompson, once again, made headlines when he stepped out to dinner with a mystery blonde in Boston on Dec. 13. Fans instantly chalked the situation up to another instance of infidelity, but not so fast. TMZ eventually reported the woman in question was his manager, Julia. TMZ’s sources said there was “nothing romantic about the dinner,” so all the hoopla was for nothing.

April 2021: Sydney Chase Speaks Out

Thompson was implicated in a cheating scandal again in 2021 when Instagram model Sydney Chase claimed she hooked up with Thompson earlier this year during an April 22 appearance on the No Jumper podcast. She claimed Thompson told her he was single, even though that wasn’t the case. "He told me he was not in a relationship anymore, so I said OK," she said. "We talked, we hung out multiple times, we went out together, everything."

Thompson vehemently denied Chase’s claims, however, and took legal action against her. In a cease-and-desist obtained by Page Six, the NBA star claimed the comments Chase made were “false and defamatory statements.” Still, reports claim the couple’s most recent split was due to “betrayal,” so it’s hard to know how much a part the Chase scandal did or didn’t play in the breakup. It’s also possible the split came after a separate incident enitrely. Their most recent decision to call it quits came after reports which said Thompson was seen entering a bedroom with three women at a party in Los Angeles on June 17.

In August 2021, Thompson and Kardashian are seemingly still separated, and it seems like it could stay that way (although the pair are seen out together regularly).