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Red Sox Have Decisions to Make and Money to Spend this Off-Season

Jon Lester (Ezra Shaw, Getty Images)

It’s been three weeks since the infamous Jon Lester trade that sent him and outfielder Jonny Gomes to Oakland for outfielder Yoenis Cespedes, and the Red Sox starting rotation really hasn’t been the same since.

Lester, the team’s best starter and home grown talent, was dealt at the trading deadline in an attempt to bolster the lineup for next year.  Reports are saying that the team is planning to make a hard run at Lester in the off-season, but doing so would likely go against their relatively new philosophy that refuses to sign a pitcher over the age of 30 to a long term contract.

Will the Red Sox sign Lester?

Assuming the team sticks to their business model, Jon Lester will probably be pitching for one of the 29 other teams in baseball, and the Red Sox will rebuild their rotation without Lester for the first time in seven years.  Should they decide to break their previously stated plan, the team would likely be paying over $20 a year for at least five years to keep Lester, who turns 31 in January.

This dilemma goes beyond whether Jon Lester himself is worth a long term contract; it forces the question of whether or not the Red Sox current method of building a team is really the best way to compete.

After what will forever be known as the “Bobby V” season, the Red Sox have stayed away from long term contracts with marquee free agents.  In the first year of this practice, the Boston Red Sox shocked baseball and dominated the 2013 regular season before rolling their way to a World Series championship.  They did this by overpaying for short year contracts with experienced veterans, but not superstars.

The 2013 Red Sox signed players like Mike Napoli, Shane Victorino, Jonny Gomes, Ryan Dempster and Koji Uehara.  These players, none of which signed a contract more than three years long, replaced the likes of Josh Beckett, Adrian Gonzalez and Carl Crawford, all of which had a high-money, long term deal with the Red Sox.

For 2013, it worked.  Mike Napoli was the team’s best right handed power hitter.  Shane Victorino played Gold Glove defense in right field and hit a crucial grand slam in Game Six of the World Series.  Jonny Gomes was the heart of the team and played an integral part of the championship run.  Koji Uehara took over as closer midseason and turned out to be the league’s best closer.  Even Dempster, who had the least value of the off-season signing, was an important clubhouse guy and innings eater in the regular season.

The Sox won the World Series, so it’s hard to argue that those signings weren’t the right move.  However, the 2014 Red Sox are far from the team that won just a single year ago, lessening the value of these deals.

The Red Sox tried this same method this past off-season, but with different results.  The bullpen had it’s share of bad signings.  Edward Mujica as been one of the worst relievers the team has had this season, posted a 2-4 record with a 4.85 ERA.  Chris Capuano started out strong (0.00 ERA in his first 12 games), but was the odd man out after a rough May and June (8.64 ERA in next 16) before being designated for assignment.  (Burke Badenhop, who also signed this past off-season, has actually been one of the better arms in relief for Boston this season.  He’s pretty much the only exception.)

The new hitters weren’t much better.  Stephen Drew, who wasn’t technically an off-season signing, stunted Xander Bogaerts’ development at shortstop and didn’t hit over .200 before traded to the Yankees at the deadline.  The Grady Sizemore experiment didn’t work.  His two year hiatus from baseball proved to be too much to overcome, and he was released before reaching 225 plate appearances.  We all know what happened with AJ Pierzynski, and the Red Sox players will be the first to tell you that his DFA didn’t come soon enough.

Of the aforementioned players, four of them have either been cut or traded.  Capuano, Sizemore, and Pierzynski were all released, and Stephen Drew was traded.  That’s a combined $21,350,000 spent on free agents this off-season that have already left the team.

Of course, every team misses on players — that’s the nature of free agency and the gamble it presents.  But with both Drew and Pierzynski, the Red Sox gave the players the highest contracts of their careers.  Drew was coming off a bad offensive postseason (defense was excellent), and Pierzynski in currently in his 17 year behind the plate.

The question then becomes about the method of off-season acquisitions.  The “overpay for one year” method of Drew and Pierzynski and the “low risk high reward” method of Grady Sizemore didn’t work this past off-season.  If the gamble goes well, General Manager Ben Cherington looks like a genius.  If it fails, the organization looks cheap.

The Red Sox have already filled all those spots with Triple A call ups and deadline trades, with comparable or better results.  The answer for this season was clear: the $21 million spent on those four players could have been better spent elsewhere.

The question for next season is similar: should the Red Sox gamble and overpay on multiple short year deals, or should they sign a big name with the extra money?  The general consensus is that Boston will need to bring in an ace in the off-season, and there’s conveniently an ace that wants to come (back) to Boston.  Red Sox fans ask yourself this: a handful of gambles that will be gone in a couple years, or Jon Lester?

Seems pretty easy to me.

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