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For Cherington, free agency could cause a draft

Posted by Tony Massarotti, Globe Staff  October 24, 2011 10:38 AM

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On the same path forged by everyone from Pedro Martinez and Derek Lowe to Johnny Damon and Jason Bay, Theo Epstein now walks. A member of the Red Sox departs. Compensation gets awarded. The machine keeps running.

Live by the system, die by the system.

And so while Epstein assumes control of the Chicago Cubs as Ben Cherington takes over the Red Sox, the irony is worth noting. During Epstein’s tenure as general manager, the single greatest strength of the Red Sox organization came in how the club managed its own free agents. From 2003 through 2011, the Red Sox selected 33 players prior to the third round of the annual draft, an average of nearly four per season that ties them with the San Diego Padres and Toronto Blue Jays for the most in baseball. That means the Sox effectively have doubled their number of high selections through compensatory draft selections, those awarded to every team when a highly-rated player is allowed to leave via the open market.

During that period, the Sox have nailed some decisions (like Martinez) and missed on others (like Damon). But above all else, the one constant under Epstein’s watch has been the steady inflow of high draft picks, the Sox all but hoarding those selections with the long-term vision or a smaller-market team (like the Padres and Jays) while possessing the big-market spending power of teams like the New York Yankees and, dare we say, Chicago Cubs.

Amid that intersection, undoubtedly, is where Cherington officially will begin tomorrow.

Here’s the basic math: as things stand, by virtue of their finish, the Sox would own the 22d and 52d picks in the first two rounds of next year’s draft. (Every team begins with two picks.) Depending on how the free agent market plays out, the Sox will either add to or subtract from those picks through whom they sign and whom they allow to depart, decisions that have more far-reaching implications that many would like to believe.

Let’s use last year as an example. When the season ended, the Red Sox were positioned to have the 21st and 51st selections in the first two rounds. Epstein subsequently went out and signed Carl Crawford (forfeiting the first-round round pick) while allowing Adrian Beltre and Victor Martinez to go (garnering a first-round selection and a sandwich-round selection for each). When the free agency dust settled, the Red Sox no longer held Nos. 21 and 51, but rather Nos. 19, 26, 36 and 40, choices they used on pitcher Matt Barnes, catcher Blake Swihart, pitcher Henry Owens and outfielder Jackie Bradley.

Of course, the Sox also traded prospects for Adrian Gonzalez, but you get the idea. While continuing to be players for high-priced proven talent – Crawford and Gonzalez – the Sox doubled their number of selections and moved up in the draft.

Given that the Red Sox still finished first in the majors in runs scored despite the departures of Beltre and Victor Martinez, the fact that they were able to significantly fortify their draft position now looks brilliant.

All of this brings us to Cherington, whose first major decisions as Red Sox general manager will concern Jonathan Papelbon and David Ortiz, both of whom will qualify as Type-A free agents – meaning that the Red Sox would likely qualify for two picks prior to the third round for each player if and when either departs. Because the market for closers is deep, Papelbon, in particular, warrants careful scrutiny. If the Red Sox believe there is a free agent closer who can perform as capably as Papelbon in Boston, then allowing him to depart makes all the sense in the world.

Here’s why: by signing a closer like, say, Heath Bell, the Sox would sacrifice their own first-round pick. Papelbon’s departure, however, would result in the gaining of two selections before the third round, meaning the Red Sox could effectively swap Papelbon for Bell while saving money and adding a high draft pick. And depending on where Papelbon ended up, the Sox might even move up in the first round, as they did last year.

For Cherington, whose obvious priority this offseason should be starting pitching, this is important for a number of reasons. For one thing, the market for starting pitchers this offseason is thin. For another, the Sox’ recent history of major free agent signings has been wretched. Boston’s best chance to add a starting pitcher may be through trade, something that would seemingly require the Sox to part with assorted degrees of young talent.

As such, Cherington will likely handle the free-agent market (or, more specifically, the compensatory selections) as if he were a bouncer working the door at a popular nightspot. For every prospect the Sox might lose in a trade, Cherington will likely make sure that one enters via the draft.

One out, one in.

And so if he can get an extra draft pick by allowing Papelbon to walk and signing someone like Bell, he might also allow himself the flexibility to deal a prospect in a trade for a starting pitcher. Papelbon then would have served the Sox on multiple levels, his departure saving the Sox money and helping to fill other holes.

During his time in Boston, Cherington now has had the luxury of working for two general managers – three if you count interim GM Mike Port in 2002 – who have built the Red Sox into what they are. Under Dan Duquette, the Red Sox acquired Jason Varitek, Derek Lowe, Pedro Martinez, Manny Ramirez and Johnny Damon through trades and free agency. Duquette, like Epstein, understood the value of high selections in the draft, which is why he refrained from signing any major free agents (thereby protecting his own draft picks) for the first four years of his tenure. By then, Duquette had drafted Nomar Garciaparra and Carl Pavano while adding prospects like Varitek, Lowe and Tony Armas, the last of whom was paired with Pavano in the deal that brought Pedro Martinez to Boston.

The Red Sox haven’t had a losing season since, qualifying for the playoffs on eight occasions while reaching the American League Championship Series five times and winning two World Series.

Now, that legacy is about to placed into the hands of Cherington, who inherits merely the most successful era in modern Red Sox history.

Don’t worry if you feel chills this autumn, Ben.

It’s just the approaching draft.

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About Mazz

Tony Massarotti is a Globe sportswriter and has been writing about sports in Boston for the last 19 years. A lifelong Bostonian, Massarotti graduated from Waltham High School and Tufts University. He was voted the Massachusetts Sportswriter of the Year by his peers in 2000 and 2008 and has been a finalist for the award on several other occasions. This blog won a 2008 EPpy award for "Best Sports Blog".

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