History hurts Shields’ chances at landing a big contract

A general manager posed an interesting question to me on Tuesday:

What is the largest free-agent contract ever given to a starting pitcher 33 or older?

The question is relevant, seeing as how the best remaining free agent, right-hander James Shields, is 33.

And the answer might help explain why the market for Shields is still unclear.

Simply put, the history of pitchers who sign big free-agent contracts at age 32 or above is not good.

Consider the six largest such deals:

*Cliff Lee: Five years, $120 million, 2011.

Lee, for the most part, was his usual brilliant self in the first three years of the deal, which he signed with the Phillies entering his age 32 season. However, he made only 13 starts last season due to elbow trouble and is a physical question entering 2015.

*Kevin Brown: Seven years, $105 million, 1999.

This one is even more incredible in hindsight; Brown was 34 when the Dodgers made him baseball’s first $100 million man. He pitched five years for the club and was successful in three of them. The Dodgers then traded him to the Yankees, for whom he finished his contract in disappointing fashion before retiring.

*A.J. Burnett: Five years, $82.5 million, 2009.

The Yankees signed Burnett entering his age 32 season, but after a solid debut with the club in ’09 he proved mostly a dud over the next two years. Only after getting traded to the Pirates did Burnett revive, finishing his contract strong with back-to-back impressive seasons.

*Derek Lowe: Four years, $60 million, 2009.

The Braves actually signed Lowe to this deal when he was entering his age 36 season. Lowe’s adjusted ERA was below-average his first three seasons in Atlanta, though he did average 192 innings and help the team win the wild card in 2010. The Braves traded him to the Indians before the final year of his deal.

*Mark Buehrle: Four years, $58 million, 2012.

This one actually has worked out pretty well; Buehrle has been his usual consistent self, averaging 203 innings and producing an above-average adjusted ERA. The Marlins signed him at age 33 and then traded him to the Blue Jays in a salary-shedding move after the first year of the deal.

*Pedro Martinez: Four years, $53 million, 2005.

Martinez was 33 when the Mets signed him at the back end of his Hall of Fame career. The move helped restore the franchise’s luster, but the oft-injured Martinez averaged under 90 innings in the final three seasons of the contract.

So, what does all this mean for Shields?

The most recent of the above contracts was Buehrle’s, and that was three years ago. Buehrle entered the market with an even greater number of innings pitched than Shields has now, but he also boasted a better adjusted ERA. Executives cite not only Shields’ age as a negative, but also his backlog of innings, declining strikeout rate and spotty postseason performance.

A five-year, $100 million deal for Shields was the original expectation by many in the industry. A four-year deal probably is more realistic, and at this point it would be a surprise if Shields received $20 million per year.