From Bobby Bonilla to Albert Haynesworth: The 3 Most Expensive Contract Mistakes in Sports History

From Bobby Bonilla to Albert Haynesworth: The 3 Most Expensive Contract Mistakes in Sports History

By Michael Harrison

February 11, 2025 at 03:43 AM

Sports history has seen some notably poor contract decisions, with three standing out as particularly costly mistakes. Here's a look at the most infamous contracts in sports:

Bobby Bonilla and the Mets

  • Gets paid $1.19 million annually every July 1st
  • Originally owed $5.9 million in 2000
  • Mets agreed to defer payment over 25 years (2011-2035)
  • Total payout will exceed $28 million
  • Known as "Bobby Bonilla Day" annually

Ilya Kovalchuk and the New Jersey Devils

  • Signed unprecedented 17-year, $102 million contract
  • Deal resulted in team fines and lost draft picks
  • Contract faced legal challenges
  • Kovalchuk returned to Russia within two years
  • One of the NHL's most controversial contracts

Albert Haynesworth and Washington

  • Signed 8-year, $100 million contract in 2009
  • Received massive signing bonus
  • Previously made two Pro Bowls with Titans
  • Performance and effort declined dramatically
  • Released within two years
  • Former teammates cited poor work ethic

These contracts serve as cautionary tales for sports franchises, demonstrating how large, long-term financial commitments can backfire when not properly structured or given to the wrong players.

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