On December 9th, 1992 Greg Maddux left the Cubs after signing with the Braves. The contract he agreed to, for five years and $28 million, was at that time the richest contract given to any pitcher. Maddux decided to leave the Cubs after seven seasons because of contentious contract negotiations. He went on to pitch 11 seasons for the Braves (from 1993 to 2003), winning three consecutive Cy Young awards from 1993-1995, bring his total to four (he won four straight overall, having won his first with the Cubs in 1992). After finishing his career in 2008, Maddux had compiled 355 wins (including 17 consecutive seasons with at least 15 wins), a career ERA of 3.16 and over 3300 strikeouts.
Of course, $28 million is miniscule compared to the richest contracts given out by teams today. Cliff Lee is rumored to have been offered a seven year, $161 million dollar offer (from the Yankees), which would tie current Yankee ace CC Sabathia for the richest contract ever given to a pitcher. At $23 million per season, that is almost worth as much as the entire contract that Maddux signed in 1992. There is no way Cliff Lee will be worth $23 million per season during the last few years of that contract (he will be 39 at the end of a seven year contract). However, the Yankees may need to pay that much in order to land Lee, which is just the way baseball operates nowadays.
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