The Bolton/Jordan Softball Game

When aimlessly wondering around Ebay I found this……….

This is the greatest piece of clothing ever produced by Nike. Ever. Ever. Ever 100X.  There is no argument you can make against it.  It’d be like arguing against the sky being blue or Guy Fieri being most annoying television personality.

The shirt commemorates the clash between Michael Jordan’s celebrity softball team the Air Force and Michael Bolton’s Bolton Bombers.  Despite taking place during the height of Rock N Jock this was probably the best celebrity softball game ever played.  I want an oral history of this game.  The country NEEDS an oral history of this game.

Meet the Bolton Bombers

Here are the most important questions that need to be answered:

Was the Air Force outfield Tony! Toni! Tone!?

How much money Jordan put down on this game?

How long Bolton hold the last syllable of the National Anthem?

What position did Oakley play?

Who batted clean-up for the Bombers, Van Damme?

How much trash did Jordan talk and how many times did he strike out?

Where was the after-party?  Stanley’s or The Hangge Uppe?

Was Will Smith invited?

Who won?

What Chicago restaurants catered the event?

Did Jodeci form the Bomber’s double play combo?

Was Jordan’s sponsor Nike and Bolton’s Vidal Sassoon?

Will there ever be a rematch and can I report on it?


Bolton’s entire team consisted of his band-mates and was coached by Frank Thomas.

The Jordan team featured, Evander Holyfield, MC Hammer, Magic Johnson, Ahmad Rashaad, and Tom Selleck.

The Jordan team was coached by Bo Jackson, who was kicked out of the game for arguing with the umpire.

Bolton played an “almost flawless” third base.

Jordan went 1-4 at the plate.

The Bolton Bombers won the game.


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Thank you to Dobie Holland and Jet Magazine for covering the event.


One thought on “The Bolton/Jordan Softball Game

  1. I was at this!!! but way too young (and in the nosebleeds) to remember details other than “omg Michael Jordan” I still have my official hat from it I believe

    I also got luckily and saw mj play bball retired at that pippen charity in game in early 95, I always got to see mj at random things as a kid (bulls tickets we’re hard to come by in the early 90s pre Internet)

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