Touching All the Bases

How should the Red Sox use the money Ryan Dempster left on the table?


For a Red Sox fan, Sunday was a day of appreciation, but hardly for reasons that would have been expected the evening before.

Ryan Dempster‘s surprising decision to step off the pitcher’s mound for the coming season led to thoughtful testimonials of genuine respect, not just for what he’d accomplished during his 16 season in the major leagues, but for his professionalism and good humor.

He did his best to improve every clubhouse he entered, an average pitcher (career 98 adjusted OPS) who bettered his team in other meaningful ways. We can say this about his one season in Boston: He certainly left the Red Sox better than he found them.

He also left them with a rather generous parting gift. Dempster’s decision to take the year off and go on the restricted list rather than spending the season collecting free money on the disabled list in essence gives the Red Sox $13.25 million to allocate any way they see fit while still remaining under the $189 million luxury tax threshold.

For a franchise that doesn’t necessarily need anything at the moment — Dempster was the sixth starter, with a half-dozen promising arms lining up behind the holdovers — it’s a remarkable spot to be in. There’s probably no such thing as an excess of pitching, but I did expect the Red Sox would eventually trade him this spring, even eating a decent portion of his salary in order to send him to, say, Milwaukee.

Now the Red Sox have that $13.25 million at their disposal. It’s very unlikely to burn a hole in Ben Cherington’s pocket, but it does give the Red Sox some appealing spending options, whether that’s shopping elsewhere or locking up someone who is already on the Red Sox roster. Here are few, some facetious, and some that really should happen:



An extension for Jon Lester: He reiterated Monday that he’s willing to take a hometown discount to remain with the only professional baseball organization he has ever known, and I don’t think anyone would be surprised if he signs an extension for, say, five years and $110 million before spring training is through. If and when the Red Sox do sign him to an extension, there’s a decent chance he gets a raise this season from the $13 million he is set to earn. Dustin Pedroia, who signed his extension last July, played 2013 at $10 million, but had his contract for 2014 and ’15 torn up as part of the new deal. No matter how it works out, no more than half of the savings Dempster afforded the Red Sox would be transferred to Lester’s bank account this year.

Use it to re-sign Stephen Drew: I think I’ve expressed a few thousand times or two where I stand on Drew, so let’s keep it to the condensed version here. I’d love to have him back because, you know, he’s a good player and you always want more good players. Besides I’m not sure Will Middlebrooks, who lost his job to Jose Iglesias and Xander Bogaerts last season, will ever repair his flaws. I suspect John Farrell feels the same way. But they’ve made Drew a standing offer, and while increasing it by a million bucks or so might convince him to make up his mind in their favor, they’ve got all the leverage. The waiting game plays on, and that’s fine.


Holding on to the majority money to acquire a player at the trading deadline: This makes the most sense, I think. Sean McAdam brought up this approach on Comcast SportsNet New England Sunday night, mentioning the name Cliff Lee hypothetically as someone who might become available in July. Lee, at 35, is still an exceptional pitcher, and the Phillies are highly unlikely to be an exceptional team. He’s due at least $62.5 million over the next three years, and that’s if he’s bought out in 2016. Otherwise, he’ll get $77.5 million through his age-37 season. Having that kind of money available to bring in a player of his magnitude is a prudent and very appealing option.

Signing Ervin Santana: Pass. He had a fine walk-year with the Royals. He also had a 74 adjusted OPS and gave up 39 homers two years ago. They have no need for him even at a bargain rate.


An extension for Xander Bogaerts: Well, sure, I know there’s a better chance of Scott Boras waiving his commission out of the goodness of his heart for the rest of his career than letting Bogaerts sign an Evan Longoria-in-2008 type deal now. If you’ll recall, roughly a week after being recalled to the big leagues in April ’08, the Rays signed Longoria to a six-year, $17.5 million deal with three club options that would have brought his earnings to $44 million. There was the perception of risk in giving that sort of money to a player with six days of service time … but you know, there really wasn’t any risk at all. The Rays knew Longoria and knew what they had, and it ended up being one of the all-time bargains in baseball’s big-money era given that he averaged more than 6 bWAR per season in that stretch. There’s no doubt in my mind that the Red Sox believe in Bogaerts to the point that they’d give him a similar extension now if they could. They know what they have. Problem is, so does Boras.


A long-term extension for a star player, possibly a power-hitting Miami Marlins outfielder, acquired in a blockbuster down the road: What, you thought I was giving up on the Giancarlo Stanton-to-the-Red Sox conjecture? No chance, slugger. Just putting it on delay until next spring, when he become arbitration-eligible and starts to make real money. The Dodgers, who seem intent on fielding six outfielders at a time at some point, will probably get first crack at him because he’s from there and they have first crack at everyone at this point. But the Red Sox have the depth and quality of prospects to make it happen whenever the Marlins realize they should deal him for a huge return before he escapes on his own volition. That $13.25 million would make for a fair chunk of his first season’s salary with the Red Sox. Jeffrey Loria could buy a lot of classy dogs-playing-poker paintings with that kind of savings.

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