Trading An Ace In Offseason Proves To Be Better Bet

Back at the trade deadline, we examined the history of teams trading an ace and receiving a prospect-laden package in return.

The impetus for our examination was the trade rumors swirling around Chris Sale, who was fresh off cutting up White Sox throwback jerseys in a much-publicized clubhouse incident.

Looking back, we found that in almost every case, a team trading a pitcher of Sale’s caliber at the deadline almost never received equal value back over time, no matter how touted the prospects received in return.

But now that Sale has been traded from the White Sox to the Red Sox in the blockbuster move of the winter, it’s worthwhile to see if teams making such a trade in an offseason, rather than at the trade deadline, come out any better when trading an ace.

As in our previous piece, we looked back at every offseason deal in the wild-card era (1995 to present) involving an ace-caliber pitcher, measuring the post-trade career wins above replacement (WAR) totals, as estimated by Baseball-Reference.com, of the players involved.

Only trades made in the offseason were considered. Our baseline criteria was two-fold. The deal must involve a pitcher who meets the following two criteria:

(1) He won a Cy Young Award within the previous three years of the trade or had been an all-star in at least three of the previous four seasons. Sale meets the latter criteria, and

(2) He was traded for at least two players who had not yet exhausted their rookie eligibility.

April 6, 1995: Royals trade RHP David Cone to Blue Jays for SS Tony Medrano, RHP Dave Sinnes, and 3B Chris Stynes.

Nov. 18, 1997: Expos trade RHP Pedro Martinez to Red Sox for RHP Carl Pavano and a player to be named later (RHP Tony Armas)

Nov. 28, 2003: Diamondbacks trade RHP Curt Schilling to Red Sox for LHP Casey Fossum, RHP Brandon Lyon, LHP Jorge De La Rosa and OF Mike Goss

Jan. 11, 2005: Diamondbacks trade LHP Randy Johnson to Yankees for LHP Brad Halsey, C Dioner Navarro, RHP Javier Vasquez and cash.

Feb. 8, 2008: Twins trade LHP Johan Santana to Mets for OF Carlos Gomez, RHP Philip Humber, RHP Deolis Guerra and RHP Kevin Mulvey 

Dec. 16, 2009: Blue Jays trade RHP Roy Halladay to Phillies for C Travis D’Arnaud, RHP Kyle Drabek and OF Michael Taylor 

Dec. 16, 2009: Phillies trade LHP Cliff Lee to Mariners for OF Tyson Gillies, LHP Phillippe Aumont and RHP J.C. Ramirez 

Dec. 19, 2010: Royals trade RHP Zack Greinke and SS Yuniesky Betancourt to Brewers for OF Lorenzo Cain, SS Alcides Escobar, RHP Jeremy Jeffress, and RHP Jake Odorizzi 

Dec. 17, 2012: Mets trade RHP R.A. Dickey, C Mike Nickeas and C Josh Thole to Blue Jays for RHP Noah Syndergaard, C John Buck, C Travis D’Arnaud and OF Wuilmer Becerra 

As you can see, teams fared much better in their prospect returns when shipping away their ace in the offseason rather than midseason, with multiple successes recently in particular.

In four of the last six instances an “ace” was traded, the players received ended up providing more post-trade WAR than the pitcher moved. While this wasn’t the case early on in these types of trades (the ace outperformed his return in the first three deals of this type), it is clear getting back equal or better value has happened recently.

Of course, it is incumbent of the team receiving the haul to actually keep the player that would help them "win" or "even out the deal, something the Twins (with Carlos Gomez) and Diamondbacks (with Jorge De La Rosa in the Schilling trade and veteran Javier Vazquez in the Johnson trade) failed to do, making the deals look worse for them in retrospect.

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Still, if history is any indication, White Sox fans can take hope in the fact that the package they received will work out, even if Sale keeps delivering top-flight performance in Boston.