Top 15 Things You Didn't Know About Floyd Mayweather's Relationships

Love him or hate him, Floyd Mayweather Jr. knows how to grab headlines. He is the most accomplished boxer of the last 20 years and one of the greatest fighters of all-time. With 49 fights and 49 wins, he is one of the few boxers to retire undefeated. Mayweather won 15 world championships and annually ranked as the highest paid athlete in the world.

However, as much as some people love Mayweather inside the ring, they hate him just as much outside the ring. His personality has been known to rub many the wrong way and even some boxing aficionados are quick to call him out for not taking on all challengers. Then there are the legal issues Mayweather has faced in his career ranging from domestic violence against women to charges of battery. Even 90 days in jail wasn’t enough to satisfy some of his dissenters as he appeared to be unapologetic after the jail stint.

Outside of the ring, and the courthouse, Mayweather is also known to be quite the womanizer. The list of women he’s been with, or been rumored to have been with, is quite extensive…and famous. Never married, Mayweather has enjoyed the bachelor life for the last 20 years and he hasn’t shied away from the publicity that comes with it. Some of the rumored romances have been simply that: rumors, and we will separate fact from fiction. Here are the 15 things you didn’t know about Floyd Mayweather Jr.’s relationships.

15 Mayweather’s Ex-Fiancee Didn’t Care That He Slept Around

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In 2013 Mayweather had a Showtime documentary which detailed his day-to-day life leading up to a fight. At the time he was dating “Miss Jackson” and the aforementioned quote about Mayweather sleeping around was presented to Miss Jackson. Her response?

“I’m not the jealous type…I just feel like when you have that type of relationship where you can be open and honest, I just think it helps the trust and it helps keep things new and fresh. So it doesn’t bother me and it’s never bothered me.”

Well then…I’m sure there were many men who wish they had a Miss Jackson in their lives after hearing that quote. Floyd and Miss Jackson didn’t last as a couple but we at least know what was NOT a reason for their breakup!

14 Floyd Spent 90 Days In Jail For Battery Of An Ex-Girlfriend

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Josie Harris accused Mayweather of battery in 2005 but did not press charges. However, five years later she again filed a police report against him for battery and proceeded with the charges. Mayweather was initially charged with four felonies and four misdemeanors. He ended up pleading guilty to one charge of misdemeanor battery and pleaded no contest to two counts of misdemeanor harassment. Mayweather was sentenced to 100 hours of community service and spent 90 days in a Las Vegas jail.

But the squabbles did not stop there for the former couple. In 2015 Harris sued Mayweather for $20 million after he told Katie Couric that she was on drugs in a nationally-broadcasted interview. He also said that he was just trying to hold her back during their altercation in 2010 which led to Mayweather’s prison stint. Harris is also working on a book about abusive relationships and she’s hoping that it can serve as a source of inspiration for women under similar circumstances to find the strength to escape these situations.

13 Contrary To Popular Belief, Floyd Never Dated Chilli

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In 2010, Mayweather appeared on the VH1 show “What Chilli Wants” which starred Chilli from the group, TLC. That sparked rumors that “Chilli wanted Floyd” but both denied that anything romantic went on between the two and both say that they are just friends. Chilli: “I am always going to be cool with Floyd. That’s my boy. I love him. He loves me. We did not have anything romantic going on.”

So Chilli just wanted a friendship with Floyd and, apparently, that’s what she got. Floyd has been romantically linked with many…many women but Chilli from TLC is one name we can cross off the list. Even if you're not dating Mayweather, you'll probably still be treated to some luxurious gifts. He seems to look after his people.

12 If You Break Up With Mayweather, He’ll Take Back All Of The Gifts

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Apparently all of Mayweather’s romantic relationships are conditional and come with a catch. He will lavish you with all of these gifts and possessions, but if you break up, then he’ll take back everything he bought you. Shantel Jackson AKA Miss Jackson (who may or may not be nasty) found that out the hard way. After dating Floyd for about four years and receiving countless gifts including cars, jewelry, and clothes; the two of them broke up and Floyd retained possession of all of the gifts. Apparently Floyd keeps all of the gifts in his name so if a situation like this arises, he can legally repossess everything. The man obviously knows about contracts from boxing for over 20 years so he essentially has “his women” sign contracts so he is in control of everything.

11 Floyd Gave One Of His Girlfriends A Custom Rolls Royce

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One of Floyd’s side chicks, who goes by the name Bad Medina, was the recipient of a brand new Rolls Royce for her birthday. The car was imprinted with “BADMEDINA” on the front and back and came courtesy of Fusion Luxury Motors. There’s no word on how high Ms. Medina is on the Floyd girlfriend scale but she seems to be close to the top as she’s also been spotted taking selfies with Floyd’s daughter. Medina was also one of many females who were invited to Floyd’s 40th birthday party last month though apparently wasn’t able to snag a red carpet picture with him judging from her Instagram. When Mayweather isn’t calling out Connor McGregor or flaunting his wealth on social media, he’s posting links to Medina’s website so apparently she has a job to fall back on if this little fling with the world’s highest paid athlete doesn’t work out.

10 Floyd And Jerry Buss Both Dated The Same Girl

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But not at the same time…we think. Dr. Jerry Buss, the former owner of the Lakers, was known to go after women one-third of his age. One of those women was Liza Hernandez who has posted numerous pictures of her and Buss together on her Instagram account. Buss passed away in 2013 but since then Hernandez has rebounded with one Money Mayweather. They were spotted boarding one of Mayweather’s jets together and have labeled each other their #ManCrushMonday and #WomanCrushWednesday. Mayweather also apparently bought Hernandez a Bugatti (along with two of his other girlfriends). Jerry Buss’ net worth was about $600 million at the time of his death while Mayweather’s is at about $400 million so hopefully Hernandez can survive with someone who’s not even worth half-a-billion.

9 Mayweather Has Four Children By Two Different Women

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Floyd has two boys, two girls, and two baby mamas. His childhood sweetheart, Josie Harris, is the mother of two boys and a girl who ranges in age from 13 to 17. Those three kids reside in Los Angeles with their mother. Floyd’s ex-girlfriend, Melissia Brim, is the mother of his 16 year old daughter and she lives in Las Vegas. Floyd also has an adopted son, Devion Cromwell, whose mother is Brim. Two years ago Cromwell told police that Floyd put him in a chokehold after telling the boxer, “You’re not my father.” (Sounds like a Jerry Springer episode). Cromwell eventually stopped talking to police so no charges were filed and there’s no word on the relationship between the two today. Also, it doesn’t appear that any of Floyd’s kids are getting into the family business like Floyd, his father, and two uncles did.

8 Floyd Dumped His Fiancee After She Had An Abortion

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Just two days before defeating Marcos Maidana in a welterweight unification bout, Floyd Mayweather revealed to the world why he broke up with his fiancée, Shantel Jackson. Mayweather posted a sonogram and ultrasound results on his social media pages. Attached to the picture was the caption:

"The real reason me and Shantel Christine Jackson @missjackson broke up was because she got a abortion, and I’m totally against killing babies. She killed our twin babies."

The ultrasound results show at least two fetuses inside Jackson who wouldn’t confirm nor deny that she had an abortion. She would ultimately sue Mayweather for an invasion of privacy and for jeopardizing her emotional well-being. Mayweather would eventually delete the pictures from his Facebook and Instagram accounts after receiving backlash but the damage had already clearly been done.

7 Mayweather’s Ex-Fiancee Is Now Nelly’s Fiancee

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After Floyd and Miss Jackson broke off their engagement, Jackson rebounded with rapper Nelly and those two are now engaged. Nelly and Jackson became an item pretty quickly after Floyd and Jackson broke up which sparked some rumors that Nelly actually stole Floyd’s girl. Nelly was quick to dispel any beef with Floyd at the same time he threw a shot at Floyd for his lack of education:

"I don't have beef with Floyd Mayweather. For the most part I think the whole thing is misunderstood. I try to understand where he's coming from which is a little hard to do, but I guess it's one of those things where he is who he is."

“Who he is” is the world’s highest paid athlete while Nelly was just slapped with a $2.4 million tax lien. The fact that Jackson would leave the wealth of Floyd for someone in Nelly’s situation says more about the person Floyd is than it does about anyone else.

6 Floyd May Or May Not Have Hooked Up With Lindsay Lohan

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In 2013 Lohan was fresh out of rehab and co-hosted a Halloween party alongside Mayweather. Lohan was dressed up as Carrie from the Stephen King novel while Mayweather played the role of Freddie Kruger. Despite posing as a couple of horror villains, the two also had plenty of time to pose together during some cozy moments. Lohan even accepted an invitation to Mayweather’s VIP booth – a booth where cameras were not allowed. Mayweather was engaged to Shantel Jackson at the time, but it’s not like a simple engagement ever stopped him from flirting before. However, chances are that if something did actually go down between the two then one of the sides would have spilled the beans by now so it’s unlikely that Freddie and Carrie ever hooked up.

5 His Baby Mamas Beefed With Each Other On Instagram

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Apparently when Floyd isn’t beefing with his exes, they are beefing with each other. But these aren’t just two of Floyd’s random ex-girlfriends, but rather the mothers to his children. Josie Harris, the mother of three of Floyd’s kids, started it off by taking a shot at Melissia Brim, the mother of one of his kids:

Brim, who is still close with Floyd and is part of “The Money Team”, quickly responded with some thoughts of her own. Needless to say, the whole situation must have caused some drama for Mayweather. His two baby mammas were probably the last two people he would ever want to get in a fight, as he probably would like to keep that entire aspect of his life peaceful and quiet.

4 Floyd Got Friend-zoned By Keyshia Cole

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Keyshia Cole is single now after divorcing former NBA player Boobie Gibson. Floyd befriended the suddenly single Cole and the singer even attended Floyd’s daughter’s birthday party. But then Floyd did something that said he wanted to be “more than friends” – he bought Cole a Mercedes-Benz. We’ve seen that Floyd loves to buy cars for women he’s romantically-involved with but here is the comment Cole put on SnapChat after Floyd bought her a Benz:

“My friend is sooo sweet for buying me this Car love him so much”

Ouch! Not “my boo” or “my man” or “bae” but “my friend”! It looks like Cole dodged Floyd’s advances better than any of his opponents ever dodged him in the ring. In a somewhat related note, Cole’s father is Virgil Hunter who is a boxing trainer and has trained numerous world champions. Boxing may be in her blood but it won’t be in her bed.

3 Floyd Lost A Girlfriend To Ray-J

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In 2013 Floyd was dating a former stripper named Queen Princess Love (not sure if that’s her real name or her stage name but I’m guessing it’s the latter). However, former BFF for Floyd, 50 Cent, then called out Love for hooking up with another known womanizer, Ray-J. There was no video involved this time with Ray-J but there were pictures confirming that he and Love were together. Once Floyd saw the pictures, he posted a note on Instagram that didn’t directly mention Love but talked about how he took her from nothing and made her into something. He also included the line “That’s why they say, leave trash in the garbage” which refers to Love’s previous life before she met Floyd. And just like that Love was kicked out of Floyd’s stable of women; however, there’s no word (or additional pics) to confirm if she and Ray-J are still together.

2 Floyd’s Current Girlfriend Is 20 Years Old

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In October 1996 Floyd Mayweather gave up his amateur status and had his first professional bout. A few months later, his current girlfriend (as of March 2017) was born. Raemarni Ball is a 20-year-old singer from England and she appears to be Floyd’s #1 girl.

But wait, there’s more…

Ball appears to be cut from a similar cloth to Mayweather as she also has another boyfriend just as Mayweather has multiple girlfriends. Ball also seems to be exactly the type of girl that Mayweather likes to have around him as judging by this quote from a local English resident who knows Ball well:

“She’s the sort of girl who wants to be a star I’d say she was a bit of a wannabe WAG.”

Something tells me that's just the type of woman Floyd prefers.

1 Mayweather May Have More Side Chicks Than He Has Cars

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Floyd has never been married but the number of women he’s been with is somewhere in between Tim Tebow and Wilt Chamberlain. Floyd was asked about maintaining relationships with multiple women at the same time, and he used a car analogy to express his views on polygamy:

“When it comes to females, even though you can’t drive 10 cars at one time, but, you got people that got 10 cars. So you’re able to keep maintenance up on 10 cars. So I feel that as far as it comes to females, that same thing should apply. If you’re able to take care of 20 then you should have 20.”

We knew that Floyd collected championship belts, cars, and even pet tigers; now we know he keeps a fleet of women as well. Some men can’t even take care of one woman, much less 20, so in a way; we have to tip our hat to Floyd for his ability to keep up with so many women.

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