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All Of Tristan Thompson's Alleged Flings & Side Chicks: Jordyn Woods, Sydney Chase, More

Jul. 7 2021, Published 3:29 p.m. ET

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Between Tristan Thompson's baby mamas, alleged flings, secret hookups, one-night stands and NBA career, one thing is for sure — the athlete sure knows how to multitask.

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Thompson has been making headlines for years over his past relationships with Jordan Craig and Khloé Kardashian — not to mention all of the alleged side chicks he apparently hooked up with while dating both ladies.

Speculation surrounding Thompson's loyalty in relationships arose when he was accused of cheating on baby mama Craig with Kardashian while Craig was pregnant with the former couple's son, Prince. The athlete and Craig dated for two years before they called it quits in 2016. Following their split, the 29-year-old gave birth to the former flames' son in December of that year.

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Meanwhile, Thompson already moved on with Kardashian, news that made headlines in September 2016. Despite the cheating rumors, the reality star and Thompson enjoyed the honeymoon phase of their relationship, announcing in December 2017 that Kardashian was pregnant with her his baby.

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(Kardashian and Thompson also addressed the cheating claims in 2019 after Craig alleged, per court documents obtained by Radar, that the NBA player's public relationship with Kardashian was damaging to her pregnancy. The Boston Celtics player insisted via Twitter that he was "single" when he pursued his romance with Kardashian, a claim the Good American co-founder doubled down on via her Instagram page at the time.)

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And while Kardashian was preparing to welcome the couple's first child together, Thompson was hit with a slew of cheating accusations just days before the arrival of the on-again-off-again couple's daughter, True.

At the time, the nine-month pregnant mama was at home in Cleveland while Thompson was with the Cleveland Cavaliers in New York. The father-of-two was seen arriving at his Manhattan hotel with a mystery woman who was identified as Instagram model Lani Blair.

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According to Page Six, the two spent four hours at his five-star hotel before they went to the private members club Soho House in the Meatpacking District. They were reportedly seen returning together at around 5 a.m. the following morning. Hours later, Blair was seen leaving the hotel at 8 p.m. in the same clothes she wore out the night before while clutching an overnight bag.

Online footage also circulated of Thompson and Blair appearing to kiss at NYC rooftop hotspot PH-D before they headed to the Soho House. Shortly after he was seen taking Blair back to his hotel, footage of Thompson allegedly cheating with two women at a Washington D.C. hookah lounge went viral. The footage, obtained by TMZ, was from October 2017, when Kardashian was three months pregnant.

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Two days after Thompson's cheating scandals made headlines, Kardashian gave birth to the couple's daughter on April 12, 2018.

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Despite a few bumps in the road — given that Thompson was accused of cheating on Kardashian twice while she was pregnant with their baby — the coparents managed to make their relationship work. However, drama plagued the couple once more when Thompson was seen kissing Kylie Jenner's ex-BFFL Jordyn Woods at a party.

And while his second cheating scandal appeared to be the last straw for Kardashian, as they called things off shortly after news broke of his make-out sesh with Woods, the mother-of-one took her baby daddy back last summer.

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Kardashian may have been hoping that third time's the charm when it comes to Thompson finally being faithful. However, he came under fire once again when Instagram model Sydney Chase claimed in April that she had a sexual relationship with Thompson after he and Kardashian reconciled in August.

According to Chase, the duo “talked … hung out multiple times … went out together, everything," because he allegedly "told [her] he was not in a relationship anymore." However, she said she cut things off with the 30-year-old when she found out he was actually spoken for.

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After making the shocking allegations on Adam22's "No Jumper" podcast, Chase doubled down on her claims in a TikTok video, adding that Thompson actually reached out to her twice since finding out about the interview, which aired April 22 but was filmed on April 8.

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Chase — who claimed that Thompson had “a peek-a-boo d*ck,” implying that he is uncircumcised, during the interview — also alleged the NBA star sent her dirty texts and told her Kardashian wasn't his type. In light of the scandalous claims made by the young model, Thompson's lawyer sent her a cease and desist, telling Chase to show these alleged messages or keep quiet.

However, the drama doesn't stop there. Last month, Thompson's alleged baby mama, Kimberly Alexander, started going after Thompson and Kardashian via social media, insisting that Thompson take a second paternity test because the first was allegedly tampered with by the powerful reality star family.

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Her social media tirade comes after the serial cheater filed a libel suit against her last year for continuing to drag his name through the mud and claim he fathered her son, despite the DNA test results. Kardashian's lawyers also sent Thompson's accuser a cease and desist after she admitted to fabricating alleged messages sent to her from Kardashian.

After receiving her second cease-and-desist letter from the former couple, Alexander shared a photo to Instagram of her son's birth certificate, which showed that her son was born July 6, 2015. Alongside her Instagram Story post bashing Thompson, Alexander alleged he cheated on his baby mama Craig, writing: "[Tristan] knows the date and is scared it will show he was a cheater once again!!!"

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Despite all the accusations made against her man, Kardashian remained by Thompson's side — until now. The famous couple called it quits last month, just hours after it was reported that the pro athlete attended a L.A. party where he was seen going into one of the rooms with three girls and a guy.

OK! reported that the group stayed in the room "for at least 30 minutes," and Thompson was seen looking like a mess when he returned to the party. News of Thompson's questionable night out comes on the heels of Kardashian revealing that she "wants more children" with her baby daddy despite his past cheating history.

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