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Floyd Mayweather Spotted Yachting With Possible Ex-Girlfriend Who Sued Him

Originally posted on KO on SI | By Grant Young | Last updated Aug 31, 2025 5:44 PM ET

While retired boxing legend Floyd "Money" Mayweather earned his global game and staggering bank account balance through his undefeated fighting career (which included 15 major world championships across five different weight classes), there's no question that Mayweather's infamy has been increased by his many endeavors outside of the ring.

Whether it's through legendary parties and club events, legal cases, beefs with other famous celebrities, insane wagers on sporting events, or rubbing elbows with other pop culture icons, Mayweather has a unique knack for remaining in headlines, despite not having fought in a professional bout since beating former UFC two-division world champion Conor McGregor in 2017 to improve his record to 50-0.

And Mayweather is finding himself at the center of attention again after a viral video of him spending time with what could be a past flame has gone viral on social media.

Floyd Mayweather Potentially Seen With Ex-Girlfriend on Yacht

When he was at the prime of his boxing career nearly a decade ago, Mayweather was dating Shantel “Miss Jackson” Jackson.

The couple were together after meeting in 2006 and ultimately broke up in 2013. Since then, Jackson moved on to begin dating rapper Nelly, but that pair has also since broken up.

However, a recent TikTok post by user @yachts_life that was posted on August 29 shows what many believe to be Mayweather and Jackson on Mayweather's yacht together. This post has gone viral, causing some to speculate that the couple could be back together.

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A post shared by What's The Word (@whats._.the._.word)

However, it must be noted that there's no clear indication that this is indeed Jackson with Mayweather. And many comments on the initial TikTok are suggesting it definitely is not her (while others are saying that it is her). Therefore, there's no way to know whether this actually is Jackson, unless one of the two sides confirms it.

If this is Jackson in the video, seeing her back alongside Mayweather on his yacht is raising eyebrows. Ultimately, only time will tell whether this couple is truly getting back together.

Mayweather and Jackson's Messy Split in 2013

This couple broke up in 2013, which prompted Jackson to file a lawsuit against Mayweather one year later, "seeking damages and alleging invasion of privacy, assault, battery and defamation," according to the Los Angeles Times.

Ultimately, Jackson dropped the case in 2021, and reports suggest that the two sides settled the dispute privately.

This article first appeared on KO on SI and was syndicated with permission.

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