Last September, SI's Jon Heyman guessed the Yankees would eventually re-sign Derek Jeter for at least $60MM over three years. Bob Klapisch of FOX Sports suggested in November that the Yankees give him a four-year, $100MM extension beginning with the '10 season. As recently as March, Heyman talked to two rival executives who believed Jeter would seek six years.
We haven't seen those kinds of contract estimates lately. Noting Jeter's reduced range to his left, Joel Sherman of the New York Post wrote on May 6th that the length of Jeter's next contract "is one of the toughest issues in the history of the organization." More recently, Sherman wondered if the prices for Jeter and Mariano Rivera will come down as they fail to match their 2009 seasons.
Jeter is currently hitting .276/.320/.396 in 206 plate appearances this season. His walks are down and he's swinging at more pitches outside the zone than ever. It'd easily be the worst offensive season of his career, though he still has plenty of time to right the ship. He had two similar offensive months to start the '08 season, but regained his form in June.
Consider this hypothetical situation. Say the Astros had drafted Jeter first overall in 1992 instead of Phil Nevin. Jeter has the same legendary career in Houston, but still reaches free agency after the 2010 season. With Jeter's game potentially slipping, the Astros decide to part ways and don't offer arbitration. The Yankees need a shortstop. What's their contract offer? I'm thinking three years, $30MM at most. Even three years might be a reach for a 36-year-old player.
Back to reality: Jeter is the face of the Yankees, and an extension seems a near-certainty. Based on Heyman's September guess, Jeter's premium could be in the range of $10MM annually, plus an extra year or two.