Originally written on The Outside Corner  |  Last updated 11/19/14

When Yadier Molina, a very good catcher, but far from a star-level player outside of St. Louis, recently became a $15 million dollar player (starting in 2013), there were more than a few people asking the question: Why? In fact, 64 percent of those who voted on our poll this past week thought the deal was “insanity” and 35 percent thought that Molina was a nice player, but that the contract was a huge overpay. Zero percent thought that it was an awesome value.

With this in mind, we turn to you once again and ask: Who holds MLB’s worst current contract extension?

And the nominees are…

Yadier Molina, 5yrs/$75M starting in 2013

Yadi’s defense is flat-out awesome and he has consistently been a 3-4 wins above replacement (WAR) player since 2008. However, his 14 home runs last season were double his previous career high and he’ll be a 35-year-old catcher by the time this extension is through. While he’s no slouch at the plate, he hadn’t exactly been an on base or extra base threat until last season, when he posted his first .800-plus OPS season.

Ryan Howard, 5yrs/$125M starting this season

The 32-year-old Howard will start his extension off on the disabled list as he continues to recover from a ruptured Achilles injury suffered during last season’s playoffs. Regardless of the fact that Howard is currently injured, many criticized this extension at the time because of Howard’s already declining numbers (both on offense and defense) and the fear that his bold body size would cause an early decline with no DH spot to turn to. Howard will be 36 by the end of this deal, at which point the Phillies either have to pay him $23M in his age 37 season or pay him a $10M buyout not to play for them. Last season, for the first time in his career, Howard posted a SLG under .500, he is a career .231/.311/.438 hitter against left-handed pitching and for two straight seasons has been worth less than two WAR according to FanGraphs’ calculations. That doesn’t seem like someone worth $20-25M per year to me.

Joe Mauer, 8yrs/$184M started in 2011

A healthy Joe Mauer probably earns every cent of this contract extension, but then again, asking for eight years of health from Mauer isn’t exactly a lock. This extension was signed in March before the 2010 season, right after Mauer had put up a career year (.365/.444/.587, 28 HR and 7.9 fWAR) and right before the Twins moved into a pitcher’s paradise of a ballpark and he came back down to earth in terms of his power (nine HR, .469 SLG). This past season, the first year of the extension, Mauer only managed to play 82 games and posted career lows in AVG/OBP/SLG (minimum of 80 games played). The Twins plan to give Mauer time at first base and DH more often going forward and, while that should help to keep him a bit more healthy, it also lowers his overall value. First basemen and DHs are supposed to hit and hit for power, while catchers who can hit are icing made of golden flakes on top of the cake.

Johan Santana, 6yrs/$137.5M started in 2008

Remember when the Mets had the money to make thse kind of deals? It was 2008 and a young Mets team led by the emerging talents of David Wright and Jose Reyes, alongside the $100M man Carlos Beltran, were looking to make a big move. They made such a move in February of that year, trading for one of the best, if not thee best, pitchers in baseball at the time. However, part of the deal that sent Johan to New York was that the Mets had to sign Johan to a long-term contract extension (he had a full no trade clause at the time).

The first year of the extension went according to plan, as Johan posted a 2.53 ERA in 234.1 innings. However, the following year, Johan would only manage to pitch in 166.2 innings and he failed (though just barely) to crack the 200 inning mark in 2010. In September of 2010, Johan underwent shoulder surgery, which caused him to miss the entire 2011 season. There are still two seasons left on Johan’s contract extension as well as a 2014 club option that can only be voided via a $5.5M buyout.

Vernon Wells, 7yrs/$126M started in 2008

This extension was a bust from the get-go. Wells put up only 1.5 fWAR combined in 2008 and 2009, but managed to find his power stroke in 2010 (31 home runs), which gave new Blue Jays GM Alex Anthopuolos the perfect opportunity to sell high and rid himself of Wells’s wretched contract. Angels GM Tony Reagins fell for the bait and aquired Wells, contract and all. Last season, Wells was a disaster, hitting only .218/.248/.412. The scary part of this deal is the fact that Wells’s contract is heavily back loaded to the tune of $21M per season for the next three years.



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