Sox To Land Santana? Hold On

It's a delicious thought for Red Sox fans: A blockbuster trade with the Twins that nets the Sox two-time Cy Young Award winner Johan Santana, who promptly joins Josh Beckett to form a potentially historic 1-2 punch atop a dynastic rotation.

But before you imagine how that Santana will look in a Sox uniform, recall the words of Theo Epstein when he explained July 31 why the Sox acquired Eric Gagne to provide bullpen reinforcement (snicker) as opposed to a blockbuster deal for a hitter such as Jermaine Dye:

"We looked long and hard at a lot of deals out there, and most deals that we looked at involved losing two or three of our absolute top prospects. And I think we made a significant addition to the club without giving up [the] Jon Lester, Clay Buchholz, Jacoby Ellsburys of the world.

"Manny Delcarmen and Justin Masterson. Jed Lowries. Brandon Mosses. Lars Anderson. I could go on and on and on. I don't want to leave anyone out."


If you're counting at home, that's eight prospects rattled off by Epstein before he stopped himself. Five of those players—everyone except Delcarmen, Moss and Anderson—have been mentioned as possible bait for a Santana trade. In other words: There's no way the Sox are landing Santana—who has pitched at least 219 innings while averaging more than a strikeout per inning every season since 2004—without dipping into their "absolute top prospects."

And to do so would run counter to the philosophies Epstein and the Sox have espoused over the last several years. The Sox have made it a priority to reconstruct a farm system that replenishes the big league club with top-notch players whose production far outweighs their minimal salaries.

After five seasons under Epstein's watch, the Sox are almost there. Dustin Pedroia won the Rookie of the Year. Kevin Youkilis won the AL Gold Glove at first base. Ellsbury could have won the World Series MVP. Lester won the Series clincher and Jonathan Papelbon clinched it. And Buchholz threw a no-hitter.

And there's more where they came from. Now that Buchholz has some major league time, Masterson and Bowden—each of whom thrived at hitter-friendly Single-A Lancaster this season—are the top two pitching prospects on the farm. And with Moss earning his first recalls this season, Lowrie, who hit .298 with 13 homers between Double-A Portland and Triple-A Pawtucket, is the closest thing the Sox have to a major league-ready position player in the minors.

To deal one or more of them would cut into the organizational depth Epstein covets. And to acquire Santana would require a contractual commitment unlike anything the Sox have done since John Henry purchased the club in 2002. It's expected that Santana will want a six-year extension worth well in excess of $20 million per season, which would make him the highest-paid pitcher of all-time.

At those prices, the Sox would almost surely get six seasons of Buchholz, Ellsbury and crew for one year of Santana. Remember that even Nomar Garciaparra, who received the most lucrative deal ever for a player with one year of service time in 1997, made just over $22.5 million in his first six years.

Plus, the Sox would almost surely be getting the best years of their careers. Santana, who turns 29 in March, is at his peak. But what kind of pitcher will he be in years four, five and six of the deal? The Sox are reluctant to pay a player on reputation, but chances are they'd be doing that with Santana in 2013.

Of course, paying $20-odd million for a declining Santana wouldn't cripple the big market Sox. But a tenet of building the farm system applies here as well: Just because the Sox have the money doesn't mean they have to spend it.

Scouting director Jason McLeod heard the grumblings when the Sox didn't come to terms with several of the high schoolers they selected in this year's draft, including third-round pick Hunter Morris. "What I would say [to fans] is take it the way I do: Our draft is an investment for the franchise going forward," McLeod said. "And all these players, it's like a personal portfolio every year. I'm going to do my best to spend John Henry's money as wisely as I can.

"So I would say if this is your money that you were investing, would you just go spend foolishly on the high-priced items that are out there because you have [money]? I don't think people would…I'm not going to be irresponsible and just buy up expensive items because the money's in the checking account."

Could the Sox still deal for Santana? Sure. The Sox have proven willing to pay a premium for proven starting pitching. Two years ago, they sent top prospects Hanley Ramirez and Anibal Sanchez to the Marlins in the Josh Beckett deal.

But Beckett was only 25 and already had a World Series MVP award on his resume. In addition, no one expected Ramirez, fresh off a listless season at Portland, to immediately emerge as one of the NL's best players. And Sanchez had already battled arm and weight problems and underwent shoulder surgery after making six starts this season.

Last year, the Sox signed Daisuke Matsuzaka to a six-year contract that includes a no-trade clause. That deal represented a dramatic departure for the Sox, who used to refuse to grant no-trade clauses or sign players for more than four years.

So Epstein doesn't deal in absolutes. But he doesn't deal his absolute top prospects, either.


Diehard managing editor Jerry Beach can be reached at diehardmag@yahoo.com. To receive a free issue of Diehard, call 888-501-5752. To subscribe to Diehard or diehardmagazine.com, please CLICK HERE

Diehard Magazine Top Stories