Earlier today, Mike Petriello wrote an article over at ESPN looking at the curse of the contract extension. Petriello pointed out a lot of big extensions that were given out from 2010-2014, well before an extension was needed. A lot of those extensions are now backfiring, such as Ryan Howard's five-year, $125 M deal, and Joey Votto's ten-year, $225 M deal, which is currently in year one and is seeing Votto miss a lot of time due to injury.
All of the deals pointed out in the article were signed two years before the extensions actually started. Most of the teams gave out contracts that paid free agent dollars, well before the players reached free agency. Had they waited until the player was actually a free agent, they might have avoided these huge mistakes. For example, Justin Verlander ...
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Tim is the owner and editor in chief of Pirates Prospects. He started the site in January 2009, and turned it into his full time job during the 2011 season. Prior to starting Pirates Prospects, Tim worked with AccuScore.com, providing MLB, NHL, and NFL coverage to various national media outlets, including ESPN Insider, USA Today, Yahoo Sports, and the Wall Street Journal. He also writes the annual Prospect Guide, which is sold through the site. Tim lives in Bradenton, where he provides live coverage all year of Spring Training, mini camp, instructs, the Bradenton Marauders, and the GCL Pirates.