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Some professional sports teams retire numbers in honor of exceptional players. If practiced frequently enough by an old team, such a practice would be unsustainable. You'd run out of numbers. More mildly, you might need to allocate a specific number to someone like Chad Ochocinco.

Has the practice of retiring numbers ever created a significant problem for a major league sports team? How do they work around it?

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It's not exactly the problem you pointed out in your OP, but the Toronto Maple Leafs (NHL team) have an ongoing dispute with one of their players from 1960-1975.

The leafs have a policy of honouring jersey numbers rather than retiring them, where a banner is raised to the rafters in honour of the player, but future players can still wear the number. Given that the leafs have almost twenty number honoured, they do this to avoid the problem you mentioned in your question. They only actually retire numbers when a player has died or suffered a career ending injury while playing for the team; they only have two numbers actually retired.

You can read more about the dispute here: Wikipedia 1, 2

2017 Update: The dispute is over: The Leafs decided to start retiring their numbers rather than honouring them, so Keon's number is now retired.

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NFL: Peyton Manning's #18 was retired in Denver, but Frank Tripucka allowed Manning to wear his retired number.(1) Kyle Orton wore #8 with the Broncos, even though he wore #18 with the Bears, his team prior to being part of the Broncos.(2)

MLB: There are two #8's (Bill Dickey and Yogi Berra) that are retired...Berra wore Dickey's number before it was retired.(3) Also, the same has happened with Ferguson Jenkins and Greg Maddux with #31 with the Chicago Cubs.

MLB: Ichiro (originally #51 for the Seattle Mariners) wears #31 for the Yankees as #51 was worn by Bernie Williams (although not retired -- most likely out of respect).(4)

NFL: #12 for the Seattle Seahawks is retired for the 12th man.(5)

And as waxeagle states:

MLB has retired #42 league wide in honor of Jackie Robinson, several players were allowed to keep the number until they retired. Mariano Rivera is the last of these players. However, all MLB players and umpires wear #42 on Jackie Robinson day.

Has the practice of retiring numbers ever created a significant problem for a major league sports team? How do they work around it?

I can't recall an instance where a significant problem occured. However, the examples above show several solutions to work around it.

  • The retired player volunteers to let a player wear his retired number.
  • The player asks permission from the retired player to wear his number.
  • If the number is not retired, it's fair game. If both careers are stellar, then both players have their same number retired.
  • If the number you originally wear is retired/worn by a significant player in a team's history, wear a different number (humility vs. pride).
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  • Your third point was recently what happened with the Cubs with Ferguson Jenkins and Greg Maddux with #31, The cubs had failed to retire the number following Jenkins and Maddux wore it, when Maddux retired they had them both come back and did a very nice combined ceremony for them.
    – wax eagle
    Sep 15, 2012 at 11:58
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    Another retired number point of note. MLB has retired #42 league wide in honor of Jackie Robinson, several players were allowed to keep the number until they retired. Mariano Rivera is the last of these players. However, all MLB players and umpires wear #42 on Jackie Robinson day.
    – wax eagle
    Sep 15, 2012 at 12:05

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