5 Win-Win MLB Trade Ideas That Need to Happen This Winter

Karl Buscheck@@KarlBuscheckContributor IIIJanuary 1, 2014

5 Win-Win MLB Trade Ideas That Need to Happen This Winter

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    While nearly every MLB trade has its clear winners and clear losers, there are the select few swaps that actually work out perfectly for both sides. 

    The Prince Fielder-for-Ian Kinsler trade from earlier in the offseason fits that mold. The Detroit Tigers got out from under Fielder's megadeal, while the Texas Rangers landed the power bat that they had long been coveting. In other words, the Tigers "won" by gaining significant payroll flexibility. The Rangers "won" by significantly upgrading their lineup—at least in the first few years of Fielder's deal. 

    With these considerations in mind, here's a look at five win-win MLB trade ideas that need to happen this winter.

    Note: Stats via Baseball-Reference.com. All salary information courtesy of Cot's Baseball Contracts on baseballprospectus.com.

New York Yankees Acquire Cliff Lee

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    The Deal

    • New York Yankees get LHP Cliff Lee
    • Philadelphia Phillies get RHP Rafael De Paula and OF Mason Williams

    Why the Trade Makes Sense for the Yankees

    New York needs starting pitchers badly. Of course, Cliff Lee would come at a steep price both in terms of prospects and dollars. Over the next two seasons, the left-hander is due to make $50 million, and he also has a $27.5 million vesting option for 2016. Last season for the Phillies, though, the veteran produced a whopping 7.3 WAR. 

    Why the Trade Makes Sense for the Phillies

    In one sense, shipping Lee to the Yankees would be a pure salary dump for the Phillies. However, this proposed deal would also provide Philadelphia with plenty of potential down the line.

    Rafael De Paula landed in the No. 4 spot on the Yankees' Top 20 prospect list, according to Jonathan Mayo of MLB.com. Mason Williams takes the No. 2 spot on the list and has a promising future, according to Mayo: "If the bat develops he has the chance to be an elite-level player." With Jacoby Ellsbury now patrolling center field, the Yankees can afford to part with Williams.

Boston Red Sox Acquire Chase Headley

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    The Deal

    • Boston Red Sox get 3B Chase Headley
    • San Diego Padres get RHP Allen Webster 

    Why the Trade Makes Sense for the Red Sox

    With an abundance of starting pitchers, the Red Sox have no room in the rotation for right-hander Allen Webster despite his strong showing in Triple-A last season. However, the club would certainly benefit from adding depth to the left side of the infield. By swinging a trade for Headley, Boston could go with Xander Bogaerts at shortstop and keep Will Middlebrooks around for insurance. 

    Why the Trade Makes Sense for the Padres

    In dealing for Webster, the Padres would be acquiring a promising young starter who can't become a free agent until 2020. Last season in Triple-A, Webster went 8-4 with a 3.60 ERA while racking up 116 strikeouts in 105 innings of work. 

    There's no doubt that the Padres would miss Headley's bat. Still, as the third baseman becomes a free agent at the end of the 2014 season, now represents the ideal time to make a move.

Toronto Blue Jays Acquire Chris Sale

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    The Deal

    • Toronto Blue Jays get LHP Chris Sale
    • Chicago White Sox get RHP Aaron Sanchez, RHP Marcus Stroman and OF D.J. Davis

    Why the Trade Makes Sense for the Blue Jays

    Earlier this offseason, Blue Jays general manager Alex Anthopoulos explained to Bob Elliot of the Toronto Sun that he was in no rush to part with top prospects Aaron Sanchez and Marcus Stroman in order to land Jeff Samardzija. 

    Chris Sale, of course, is no Samardzija. The tall left-hander is a substantially better pitcher whose addition would catapult the Blue Jays back into contention in the AL East.

    In 2013, Sale earned his second straight All-Star berth as he went 11-14 with a 3.04 ERA. Sale also posted a 6.9 WAR and reeled off 226 strikeouts, the third-highest total in the American League. Plus, the starter will be under club control for six more seasons. 

    Why the Trade Makes Sense for the White Sox

    Trading Sale certainly won't help the White Sox avoid another 99-loss campaign in 2014. Then again, that might not matter much, as the club appears unlikely to compete for the AL Central crown with the Tigers, Kansas City Royals and Cleveland Indians all standing in their way. 

    However, by 2015 the team could be absolutely loaded. Already this offseason, the White Sox have acquired intriguing young players like third baseman Matt Davidson and center fielder Adam Eaton.

    Bringing in Sanchez and Stroman would seriously replenish the organization's pitching depth. In a couple of years, Sanchez could supplant Sale as the White Sox ace. D.J. Davis meanwhile was "widely considered the fastest player in the 2012 draft," according to Brendan Kennedy of the Toronto Star.

Baltimore Orioles Acquire Ike Davis

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    The Deal

    • Baltimore Orioles get 1B Ike Davis
    • New York Mets get RHP Mike Wright

    Why the Trade Makes Sense for the Orioles

    Now is the perfect time to buy low on Ike Davis. Last season, Davis slumped to a .205 average with just nine home runs after crushing 32 long balls back in 2012. 

    According to Eduardo A. Encina of The Baltimore Sun, the Orioles were unwilling to pull the trigger when the Mets asked for Eduardo Rodriguez in exchange for Davis. Rodriguez ranks as the Orioles' third-best prospect, according to Jonathan Mayo of MLB.com. The Orioles could be more open to moving Mike Wright, who ends up in the No. 6 spot in Mayo's rankings. 

    Why the Trade Makes Sense for the Mets

    The Mets appear ready to cut their losses on Davis. As Mike Puma of the New York Post tweets, the club has been "talking" with the Orioles, Milwaukee Brewers and the Pittsburgh Pirates about trading the first baseman. 

    Wright could prove to be a shrewd pickup for New York. Last season in Double-A, the right-hander went 11-3 with a 3.26 ERA. According to Mayo, Wright can hit 95 mph on the radar gun, and even if he doesn't make it as a big league starter, he could still develop into a useful piece out of the bullpen.

Los Angeles Dodgers Acquire David Price

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    The Deal

    (Note: The following deal was originally suggested by an unnamed assistant GM to Peter Gammons of GammonsDaily.com.)

    • Los Angeles Dodgers get LHP David Price
    • Tampa Bay Rays get SS Corey Seager, OF Joc Pederson, LHP Julio Urias and RHP Chris Withrow

    Why the Trade Makes Sense for the Dodgers

    A one-two combo of David Price and Clayton Kershaw would be downright scary. Add Zack Greinke and Hyun-Jin Ryu into the equation, and it begins to make sense as to why the Dodgers would agree to part with such an assortment of minor league talent. 

    The Dodgers could easily get burned down the line for dealing away players with the upside that Corey Seager, Joc Pederson and Julio Urias boast. By acquiring Price, though, the Dodgers would immediately overtake the St. Louis Cardinals as the team to beat in the National League in 2014. 

    Why the Trade Makes Sense for the Rays

    The Rays would likely prefer to get more MLB-ready talent. However, the chance to land Seager, Pederson and Urias (not to mention Withrow) in a single deal, could just prove to be too good of an opportunity to pass up. Plus, there is an excellent chance that Seager and Pederson could be key contributors for Tampa Bay beginning in 2015. 

    If you want to talk baseball, find me on Twitter @KarlBuscheck.