From there, videos and photos cascaded from sites like The Shade Room and TMZ that claimed to show the NBA player cheating with multiple women. Khloe later confirmed these reports and forgave Thompson ( though she did not forget ), but nearly one year later, the couple has been hit with yet another scandal.
It's been widely reported that Thompson cheated on Khloe again with a close Kardashian confidante: Kylie Jenner's best friend, Jordyn Woods.
If you've been following the couple's three-year relationship, you'll know that Thompson's reputation has been hazy from the get-go. Here's the full timeline of his rumored infidelity.
Thompson and Khloe began dating while his ex-girlfriend of two years, model and blogger Jordan Craig, was pregnant.
Thompson and Craig were together for about two years , from 2014 to 2016, butit's unclear exactly why they broke up. Neither have addressed their relationship since, and Craig never commented on his relationship with Khloe, which sparked in the summer of 2016 after a successful blind date.
"When Khloefirst started dating Tristan, her family questioned if it was a good idea. There were several concerns, including that he is another basketball player and also that his ex was pregnant," an unnamed source told People . "It took a while for the family to accept Tristan. They were worried that Khloe would end up heartbroken."
"I feel like Khloe always dives into relationships and puts her whole heart into everything," Kim told DeGeneres.
Shortly after Thompson and Khloe went public with their relationship, sources claimed that he was a cheater with an existing "side chick."
The site cited a source who claimed that Thompson and Craig broke up because of his "cheating ways."
Khloe has never publicly acknowledged the birth of her boyfriend's first child. And while the new father did not acknowledge the birth on social media, he did post a photo of himself and Khloe together on Christmas, two weeks later.
"Merry Christmas & Happy Holidays from me and mines, to you and yours," he wrote.
About two weeks after the news broke that Khloe and Thompson were expecting their first child together , he was filmed fooling around with two other women.
Just before the birth of True Thompson, TMZ published a surveillance video that was reportedly taken back in October when Khloe was three months pregnant of Thompson appearing to cheat on her with two women at a hookah lounge outside Washington, DC.
The video was recorded on October 7, 2017, the night before Thompson and the Cleveland Cavaliers played the Washington Wizards.
Once Khloe confirmed her pregnancy in December 2017, Twitter was aflame with the allegation that Thompson had cheated on his pregnant ex with Khloe.
Although the rumor had obviously been floating around social media for months, it didn't seem to gain much traction until Khloe's pregnancy was confirmed.
"OK but he cheated on his pregnant ex with u so what makes u think he won't do the same now," one commenter wrote on her announcement post.
Twitter user @rosechocglam also expressed disdain that Thompson had rarely if ever acknowledged his son Prince on social media, "but was happy to pose for a pregnancy announcement with Khloe."
"Jordan andTristanhad split already when he met Khloe, so he didn't desert her at all, and they're actually pretty good friends still, all things considered," the source told the site.
On Tuesday, April 10, nearing Khloes due date, photos and videos surfaced of Thompson with another woman in New York City.
The alleged encounter was caught on video, which the Daily Mail published. The unnamed woman who filmed it told the site,"I was there and he was on the table right next to us with a group of friends and one girl who he was obviously making out with all night."
Meanwhile, the "Revenge Body" creatorhad been nesting in Cleveland as she awaited the arrival of their daughter.
"Tristan has been consistently cheating onKhloe. He's a serial cheater. And there will be more women to come out of the woodwork," a source told People . "[Family and friends]are heartbroken forKhloe. They didn't realize how deceptive Tristan could really be."
Thompsons ex reacted to the news on social mediashortly after reports of his infidelity broke.
While fans flooded Craig's social media with comments like "you won" and "Karma's a b----," she seemingly took the high road with a message on her Instagram story.
"If you respect yourself and you respect others, you would never make light of the misfortune of anyone, nor would you feel indemnified when it comes at the expense of others," Craig wrote. "Wishing peace for everyone."
Other people close to Thompson were apparently less than shocked about the news.
"None of his friends are surprised by this and they all know he cheats," one source told Us Weekly . "Most of his friends and people in his circle also cheat and don't think there's anything wrong with it."
Despite the cheating rumors, Thompson was with Khloe for the birth of their daughter.
Khloe revealed that their daughter is still taking Thompsons last name.
" Our little girl, True Thompson , has completely stolen our hearts and we are overwhelmed with LOVE," Khloe wrote. "Such a blessing to welcome this angel into the family! Mommy and Daddy loooooove you True!"
"She has one foot out the door but is also holding on to the fact that her and Tristan can make it work," the source told the site. "She hasn't given up on him yet, but also hasn't really been focusing on their relationship. When they see each other, it is all about the baby and parenting together. Khloe has fallen in love with him all over again, watching him be a dad to True, but [she also] knows she needs to really take a step back and make the right decision."
Kim seemingly confirmed the allegations during an interview with Ellen DeGeneres.
In an interview that aired in full on Monday, April 30, DeGeneres asked Kim what she thought about "poor Khloe."
"I think everybody was heartbroken for her. I mean, literally days before she gives birth, her boyfriend is seen on video cheating. And, uh, you have opinions about that?" DeGeneres asked.
"I'm gonna keep it cute and keep it classy and not talk too bad I'm gonna try not to say anything so negative 'cause one day, True is gonna see this," she told DeGeneres, but went on to reiterate that the situation is "just so messed up."
DeGeneres also asked if Khloe and Thompson are "still trying to make it work."
"I think she's not thinking of anything, I think she just wants a clear head and just wants to be alone with her baby and figure that out," Kim said. "She wanted to have some alone time with the baby and figure out what her next steps are. I think, it must be so hard to have your heart broken and fall in love all in a day or two, all happening at the same time ... she's gonna get through it."
Kris called the cheating scandal "unexpected."
"It's your daughter and she's about to have a baby," DeGeneres said. "Then that video comes out of him ... you must have been furious."
"I'm there to support my kids no matter what happens," Kris said. "I just do the best I can, just like anybody else would for their family ... we're a force to be reckoned with.
"Khloe is amazing. I'm so proud of that kid.I get choked up because she's such a good mom and honestly I get so emotional.She's just concentrating on that, just being a mom, her baby, and I think that's what her sisters are doing as well. She's so excited about motherhood."
Khloe and Thompson remained a couple.
Khloe finally spoke out about criticism of her decision to stay with Thompson.
Although Khloe had posted a number of cryptic quotes and messages since the birth of her daughter, none were explicitly commenting on her relationship with Thompson until she responded directly to a fan who called her a "hypocrite" for staying with him.
"You have no knowledge of what goes on in our household or the enormous rebuilding this takes to even coexist," Khloe responded. "I'm proud of my strength. I appreciate your opinion and I hope you hold that same opinion to everyone else who has stayed in situations."
The fan claimed that she just feels "protective" of Khloe and that she doesn't want "some lame breaking [her] heart again."
"I love you for that and girl trust me don't I understand!!! I appreciate you," Khloe replied.
The new mom also hit back at a headline from the Daily Mail, which suggested that a recent dinner with Thompson was "VERY tense."
"You make up anything!! I actually had a great night," she wrote on Twitter. "It was a large birthday dinner for friends and as a new mom IM TIRED AF!! Being out past 10pm is not where I'll have the most energy these days."
Khloe has since directly addressed her boyfriends alleged infidelity.
"I'm not acting as if Tristan didn't cheat. I'm saying the story about marriage and anyone insinuating that they know what we speak about privately is 'crap,'" she wrote. "Not upset by commenters. Not upset by anything. Only pointing out when blogs create stories for you all to believe when it's just simply untrue."
On February 19, 2019, reports surfaced that Khloe and Thompson had split because he had cheated on her again with a close friend of the family.
According to Lee, a Hollywood Unlocked contributor was also at the party and witnessed Woods sitting in Thompson's lap, the two getting "touchy feely," and staying together overnight.
"That happened, that's a fact. And I don't wanna hear nobody trolling Khloe, talking about, 'It's a Kardashian curse. It's Khloe's fault.' No. If a n---- ain't s---, he ain't s---," Lee says in a video posted to the Hollywood Unlocked Instagram account. "And the fact that Kylie your best friend was at the house doing all that? Get her out now. And get him out, too."
What's more, Khloe and her best friend Haqq appeared to confirm Lee's account. Both commented on the post with approving messages. Haqq even wrote, "STRONG FACTS."
Haqq also commented on another video of Kylie's daughter Stormi saying "bye" repeatedly, with a caption that jokes about Kylie evicting Woods from their shared house.
"These hoes ain't loyal," Haqq wrote.
For what it's worth, Khloe has not posted a photo of or with Thompson on Instagram since the birth of their daughter. Khloe, Kylie, Kim, and Kourtney all still follow Woods on Instagram. Haqq unfollowed Woods on Tuesday night.
Representatives for Khloe Kardashian didn't immediately respond to INSIDER's request for comment. INSIDER will keep this post updated with any new developments.
