Celebrating Valentine's Day with the Most Memorable Michael Jordan V-Day Cards

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Valentine's Day is officially here. Long before the adult pressures of finding the right restaurant, the perfectly red bouquet of roses or saying the just the right thing in a well-thought-out $10 greeting card, Michael Jordan graced us with his presence on Valentine's Day cards produced by Cleo in 1991.
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The 1991 NBA season was a monumental one in the iconic career of the G.O.A.T. Jordan's Chicago Bulls became world champions for the first time, beating Magic Johnson and the Los Angeles Lakers in the NBA Finals. The 1991-92 season saw Jordan garner his eighth consecutive All Star game nod. "Air Jordan" also led the league in scoring for the sixth consecutive season and captured his third NBA MVP Award. Simply put, he was the man.
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Being a child (and a huge Michael Jordan fan) of the late 80s and early 90s, I think most of my buddies would still get a laugh out of getting a Michael Jordan Valentine's Day card but my wife... not so much.
Let's be honest, anything with Michael Jordan's likeness is highly collectible, but there isn't a lot of monetary value in these fun middle school artifacts.
With that being said, nearly 1,000 cards from the 1991 Cleo Michael Jordan Valentine's cards have been graded by PSA, including one autographed card. Talk about making someone's Valentine's Day unforgettable.
There are 21 different unnumbered valentine's in the '91 Cleo set, including the red border and the rare pink bordered parallel. I use the words rare and parallel very loosely.
Below, we will review a basket full of the coolest, most interesting, and most memorable 1991 Cleo Michael Jordan Valentine's Day cards. We found a number of interesting phrases and quotes on these bad boys but, luckily, we left all the X's and O's on Phil Jackson's clipboard.
1. Have a high-flying day!

The list could start and end with this great card. Using one of the most iconic images from one of the most iconic moments from Jordan's career, the "Have a high-flying day!" Valentine shows Jordan in the middle of his iconic final round free throw line dunk at the 1988 NBA Slam Dunk contest. After dueling Dominique Wilkins and his 360s and never-ending array of windmill jams, MJ took the title home.
2. Have a jammin' day

See above. This image of Jordan going up-and-under was also captured at the same Slam Dunk contest. MJ is pictured in his classic White Jordan 3's just as he punches the ball through the net with the classic old school Gatorade logo flashing on the jumbotron high above Jordan's home court in Chicago. We would definitely be having a jammin' day if we got this Valentine card back in 1991. About a third of the cards in this set offer images from the Dunk contest. We will do our best to limit those choices on our short list. No promises, though.
3. Teacher, you're the best!

In recent years, we've seen viral videos of students chipping in and buying their favorite teachers pairs of Jordan's, all but bringing the educator to tears. We aren't quite that resourceful or proactive. We'd be remiss if we got too far into the list without offering a Valentine for the head of the class from the head of the NBA class. This great image shows Jordan and his classic follow through on his signature jumper with some pretty spectacular fireworks in the background, much like Jordan set off through his entire career. Please don't do that in class, though.
4. You're "IN"

This vertical Valentine showcases a signature Jordan two-handed jam with the words You're "IN". In what you ask? In as a friend? In the cool club? In the game? I don't care what it is... we're in.
5. Hey, FRIEND! I'm on your team!

There are a lot of unnecessary exclamation points throughout these classic cards. Jordan is seen in the that sweaty, middle of a game classic pose of his hands tugging on his own shorts. If Michael Jordan ever said "Hey, FRIEND! I'm on your team", that wouldn't just make your Valentine's Day that would make your millennium. This V-tine also saves a few minutes of game time at recess by getting the selection process over with early.
6. Valentine, you're right up there! Cool!

Cool indeed. This image shows Jordan in mid-air right before he's throwing down a classic one-handed jam. The background shows the bright stars of a night sky as the cut out Jordan is flanked by two hearts and the bright red border around the card itself. This is a pretty cool image for the time. The red bordered card coupled with the red Bulls jersey and the red of the PSA slab border and logo make these guys pop in person.
7. No one could fill YOUR shoes!

Again, we fly back to the 1988 Slam Dunk contest. (Do you really blame us?) This was captured in the middle of Jordan's reverse two-handed jam. Just the simple fact that the card refers to shoes, with that being such an important aspect of Jordan's cultural significance, we had to throw that one on the list. Those beautiful bright white cement threes kick this card to the next level. As an added bonus, we offer up the pink bordered version.
8. Lookin' fine!

There are a few cards in the set that show Jordan in street clothes and out of his Bulls uniform, this being one of those such cards. Dressed for the occasion, Jordan is seen in a black tuxedo with a bow tie and the words "Lookin' fine!" with a red heart over his shoulder. If "His Airness" said you were looking fine, you would be having one heck of a Valentine's Day.

Tony Reid spent more than a decade covering combat sports at the highest level. He has written hundreds of articles and conducted hundreds of interviews about sports collectibles for such publications as Beckett, Sports Collectors Digest, and Sports Collectors Daily. Reid worked full time at a sports card shop in Central Pennsylvania for a number of years. A lifelong collector, Tony treasures his rookie card collection of star players in baseball, basketball, and football. If you want to discuss the greatness of Michael Jordan, Bo Jackson or Ken Griffey Jr., you can reach him at @tonyreidwrites on all social media platforms