TheSportster.com

15 “Not So PG” Pictures Of Women Michael Jordan Hooked Up With

From porn stars to mainstream celebs to even unknown mistresses, Michael Jordan sure loved his women!

We’re all well aware of MJ’s fantastic on-court accomplishments. A six-time NBA Champion, six-time Finals MVP, 14-time All-Star, seriously, you guys get the point. He’s regarded as a basketball God and for good reason. In this article however, we put all those records aside and take a look at a different kind of stat line, his hookup history from the past. By the time you’re done reading this list, we want to know, does his past hookups compare to his on-court accomplishments? For the likes of A-Rod, Cristiano Ronaldo, Tiger Woods and Michael Phelps, we might be able to say yes given the beauties they hooked up with. Let us know if MJ lived up to the hype off the court as well like his peers.

From adult stars to mainstream celebs to even unknown mistresses, we’ve got females from everywhere on this list. We’ll celebrate these hookups and relationships with some “Not So PG” pictures, both from the past and present.

Enough of the talk, let’s get started. Here are 15 “Not So PG” pictures of women Michael Jordan hooked up with. Like always, be sure to pass along the article to a friend. So without further ado, let's begin the list with a familiar name, and one even Tiger Woods himself might be a little too familiar with!

15 Loredana Jolie – The Athlete Lover

via nydailynews.com

If Loredana Jolie is a name you’re familiar with, that’s likely because of two reasons, one, you’re a subscriber to past editions of Playboy magazine, or two, the more likely reason, you’ve heard of her name through The Sportster. We recently featured the Playboy Bunny in an article featuring Tiger Woods hookups. Seems like Jolie’s been around the block and back again, having a thing for high profile athletes.

Jolie discussed constantly flirting with Jordan, however, she did take a shot at number 23 making the claim that he didn’t compare to Tiger Woods in more ways than one, yikes! Now we can’t confirm if this statement is accurate, but we can confirm Tiger’s got a little more experience with the ladies. We honor Jolie’s high profile hookups by ogling at the “Not So PG” picture above, ironically taken in a bedroom.

14 Janet Jackson – High Profile Romance

via pintrest.com

Before we dive into this rumored affair, let’s take a minute to enjoy the throwback picture above of Janet during her prime. From the water in the background to her pose, she seriously looks like a Goddess type sea creature. In terms of high profile hookups from Mike’s dating history, this one is right up there.

The details of this alleged affair are kind of sketchy and shady due to the fact that Jordan was married while they apparently hooked up in the past. As for Janet, she also had a hefty marriage history usually ending in divorce, her romance affairs began in 1984 marrying James DeBarge. She then had two other failed marriages in the 90s and 2000s with Rene Elizondo Jr. and Wissam Al Mana. Looking at both their troubled history in finding permanent love, we have reason to believe the rumored hookup has some validity to it.

13 Vanessa Williams – The Girlfriend

via pintrest.com

Age 54 nowadays, Williams looks quite different in comparison to the “Not So PG” throwback shot above. However, in her 50s, she’s still a smoke-bomb today and we’ll prove that in a later entry. For now, let’s discuss this high profile hookup of two big time celebs, for those of you not familiar, Williams has done it all from being a designer, singer and actress. According to the gossip, the two not only hooked up but even dated until a certain point. The time frame is kind of sketchy, but it’s said they parted ways due to different interests... oh if we have a nickel every time we’ve heard that line.

Similar to Janet in the entry above, Williams has also endured a tough go searching for love. She’s been divorced twice, although it seems like she’s finally found something permanent with Jim Skrip as the two made it official in 2015.

12 Kylie Ireland – The Adult Star

via pintrest.com

We’ve seen this example countless times in the past when it comes to high profile athletes and when you really stop and think about it, as disturbing as it sounds, it does make sense. When looking for “Not So PG” type of love, an athlete will sometimes search for the very best in that field, enter an adult star.

Michael’s not alone, as even the likes of Tiger Woods, Michael Phelps and even, pretty boy Cristiano Ronaldo have “dipped” into the adult star world when searching for love. Ireland took this “Not So PG” hookup to the public masses making the statement that she slept with Jordan in the past. Of course, MJ did not answer the allegations, leading us to believe the speculation is likely true.

11 Ashley Dupre – Another “Not So PG” Hookup

via celebitchy.com

We have reason to believe MJ was a monthly subscriber of Playboy magazine back in the day as this is yet another hookup with links to Playboy. Back in the 80s and 90s, the magazine had immense popularity which likely intrigued MJ that much more. The beauty we showcase in this “Not So PG” beach picture is a recent shot of Playboy Bunny Ashley Dupre. According to the gossip mill, the two had a brief relationship during the early portions of the 2000s.

Dupre’s name would stay in the headlines for all the wrong reasons as it was later revealed that she was also working as an illegal call girl. Alarm bells instantly went off, especially due to this rumored hookup. Without a doubt, this is a “Not So PG” hookup Mike wants to keep in the past, well, in truth, like most of them on the list.

10 Nicole Murphy – Beach Beauty

via pintrest.com

Before we discuss this rumored affair, holy goodness what a smoking hot picture this one is. In terms of quality “Not So PG” pictures from this list, man is it ever hard to top this shot, which is also a candid snap. When you look smoking in a candid shot, that’s when you know you’re doing something correct visually folks!

As for this hookup, it’s rumored the two briefly got into it following Nicole’s divorce to long-time husband Eddie Murphy. The two were married for over a decade getting hitched in ’93, but finally ending things in 2006. Seems like Nicole has a thing for athletes as she partnered up with Michael Strahan in 2009, once again, things didn’t work out as they broke up in the summer of 2014. How both Mike’s let this girl slip away, we’ll truly never know. On the other hand, Eddie probably does....

9 Karla Knafel – The Mistress

via wp.com

Sadly, another harsh truth in the world of pro sports is the fact that some athletes have a type of mistress on the side, just ask our “Not So PG” buddy Tiger Woods who had a collection of those women. For Jordan, Knafel was his “Not So PG” mistress from ’89 all the way to 1991. The two hooked up on the regular and it's rumored Jordan offered his former mistress a quarter of a million to keep things private. Karla ended up changing her mind demanding $5 million and that’s where things took a turn for the worst.

The rumors would only get more ridiculous with Karla claiming she was going to have Mike’s kid. Yup, it was bad. As for the picture above, we understand it isn’t the most “Not So PG” shot, but the meaning behind it certainly is.

8 Ashley Dupre – Cover Girl

via nbcconnecticut.com

It looks like Playboy tried their absolute best to cash in on Dupre’s 30 seconds of fame by putting her on the front cover of the May 2010 issue. The magazine was all over the story and you can see for yourselves on the headline on the front cover that reads, “An American Affair Ashely Dupre And The Seduction Of Power”. In truth, after reading that one out loud, it sounds more like a “Not So PG” adult flick than a darn article title. But hey, who are we to talk with the title of our article, seems like we’re shooting an adult documentary on MJ.

Nowadays, Ashley is trying her best to keep things a little more quiet. She’s got time on her side being a lot younger than MJ, recently entering her 30s at the tender age of 32.

7 Vanessa Williams – A Recent “Not So PG” Beach Shot

via dailymail.co.uk

We promised and like always, we delivered with this recent shot of the stunning Vanessa Williams rocking a bikini top to perfection. Oh, and to refresh your memories, she’s in her 50s as we stated earlier in the piece at 54. Maybe MJ might be inclined to rekindle this old flame? Okay, we joke, we joke, too far.

In terms of popularity, Williams is certainly up there in terms of MJ hookups. Of course, she was the first ever African American Miss America winning the honors back in the early 80s, 1983 to be exact. Nowadays, she’s put acting and singing on the backburner, focusing more so on the fashion side of things. We wonder if Mike has contacted her for any fashion tips? Likely not.

6 Loredana Jolie – A Little Throwback

via bjuniors.myblog.it

So in case the first “Not So PG” shot of Jolie didn’t do enough justice, this throwback picture should ensure the reader as to how she was able to hookup with the likes of Tiger Woods and Michael Jordan. Jolie wasn’t hiding any of the affairs as she spoke openly about both, even writing about them in her autobiography. As we stated, she spoke glowingly about her time with Tiger, claiming he knew what he was doing. Judging by his history with the ladies, that really shouldn’t shock anyone. As for her time with Jordan, she wasn’t as enthuse saying very little, and even taking a shot at MJ claiming he didn’t match up to Tiger.

We celebrate Jolie’s twisted sexual experiences with this “Not So PG” shot in where she poses on a rail that might be outside of the homes of either Tiger or MJ...

5 Juanita Vanoy – The Ex-Wife

via divorcedebbie.com

Finding a “Not So PG” picture of MJ’s ex Juanita was no easy task. We seriously had a better shot at finding a picture of a shirtless MJ outside of a Home Depot.... but seriously though, this was the best we could have done as the two look into the camera during this not so recent throwback picture.

The couple had a lengthy marriage which began way back in 1989. The couple started a family together with three kids; two boys, Jeffrey Michael and Marcus James, along with a daughter, Jasmine. The two would later suffer from an ugly divorce, which was made aware to the public back in 2002. Get ready for this one, when it was done with, Juanita walked away with $168 million from the marriage.... now that’s a load of cash folks.

4 Janet Jackson – A Recent “Not So PG Shot”

via trbimg.com

After posting the throwback “Not So PG” shot of Janet, we assume most of you were probably thinking, “hey, I wonder if she’s still hot”. Judging by this recent “Not So PG” shot above, we can safely say yes, at the age of 51, the beauty can still rock the hell out of a photo-shoot and it really shouldn’t surprise anyone, especially some dude named MJ. She’s even showcased her fantastic new body in divorce court as she dropped a boat load of weight recently. In all likelihood, her ex-husband was sweating a little more seeing that.

Nowadays, Jackson is still on tour with her Unbreakable World Tour. Although according to recent news, she plans to settle down soon and move back to LA spending time with her son and family.

3 Nicole Murphy – Candid & Glutes

via pintrest.com

We seriously could have done an entire article on “Not So PG” pictures of Nicole Murphy, but in truth, that has little to do with anything sport related (maybe we could have done 15 reasons why MJ and Michael Stahan screwed up badly?). The beauty has a slew of fantastic pictures available online, whether that be actual in studio shots, or even candid pictures such as the one you see above looking like a perfect ten inside of the water.

Oh, and it seems like Michael Strahan showed her a thing or two about squats.... good Lord! Either that, or she’s been eating carbohydrates on the regular, either or, this picture drops your jaw. We hope Mike isn’t scrolling down this list or it might cause him to reignite this old flame!

2 Kylie Ireland – The Adult Star In Her Prime

via adultdvdtalk.com

Six-time NBA Champion, you can put a check mark next to it, sleeping with an adult star, you can also put a check next to that one. If the other “Not So PG” Kylie Ireland picture wasn't enough, we decided to include another picture of the adult star during her prime, rocking the blonde head of hair. Looking at such a smoking pic, you likely understand a little bit more why MJ was so darn tempted to make such a decision.

Age 47, Ireland is still working in the adult industry flaunting her stuff. As for MJ, he’s happily married and likely taking out his frustrations on a Craps Table somewhere in Vegas. It looks like his hookups are a thing of the past at the age of 54, and being happily married to wife Yvette Prieto. Speaking of Yvette....

1 Yvette Prieto – “Not So PG” With Julio Iglesias

via thesocialmediatoday.com

Mike’s current love is none another than the beautiful Yvette Prieto. The two met and dated for quite some time, Jordan finally tied the knot with the American-Cuban model in April of 2013. They’ve built a family ever since as Prieto gave birth to a pair of twins a couple years back in 2014.

Despite being a model, Yvette in a “Not So PG” habitat is rather difficult to encounter, in truth, she’s a classy wife given her content available online. However, we showcase this “Not So PG” magazine throwback cover of the future Mrs. MJ, alongside Julio Iglesias as the two seem a little too close for comfort in this throwback magazine shot. We doubt MJ picked up an issue, instead, he’s likely still a happy subscriber of Playboy magazine...zing!

Give TheSportster a Thumbs up!

Looking for an AD FREE EXPERIENCE on TheSportster?

Get Your Free Access Now!

More in NBA

15 “Not So PG” Pictures Of Women Michael Jordan Hooked Up With