Jordan won three straight NBA titles with the Bulls and all of a sudden quit to play baseball. My feeling is that the decision had to do a lot with his father, who had recently passed away at the time. His dad loved and played baseball himself.
He played America's pastime and realized that he had more fun on the court, (or maybe the way it happened in Space Jam is right), and came back to the Bulls. He again won three straight titles for Chicago and retired afterward...again.
If he had stayed the first time, the Bulls could have easily won eight consecutive championships. Then the old SNL skit would have been right when one of Bob Swerski's pals predicted an unbelievable 'eight-peat'.
Jordan contemplated making a second comeback and finally did with the Washington Wizards, (a team in which he had part ownership but had to give up to play).
At the age of 40, Jordan came back to prove to himself that he still had the ability to play with the young guys. If you watched him closely, you saw that the ability was no longer there for the full 48 minutes.
So, when is it time to let the game go?
I think Phil Simms summed it up pretty well when he said, "When you first think about retirement, play three more years than quit." That's probably the smartest thing Simms has ever said since his retirement.
It also may be time to go when the game itself no longer wants or needs you. And if these players were smart, they would know exactly when that time comes.
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