Andrew Bailey to the Red Sox: Who Are the Winners and Losers in Deal with A's?

Ben Shapiro@benshapironyc1 Analyst IIIDecember 29, 2011

Andrew Bailey to the Red Sox: Who Are the Winners and Losers in Deal with A's?

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    Last season, the now former general manager of the Boston Red Sox, Theo Epstein, made a big trade for Adrian Gonzalez and an equally big free-agent signing when he snagged outfielder Carl Crawford. 

    New general manager Ben Cherington hasn't dipped into the free-agent market, but he hasn't been too gun-shy about pulling the trigger on trades. 

    When the Red Sox take the field on Opening Day 2012, the guys who emerge from the bullpen for the key innings are going to be totally different than what Red Sox fans have grown accustomed to. 

    Daniel Bard looks to be headed toward the starting rotation. 

    Jonathan Papelbon will be closing games out in Philadelphia

    It's going to be the Melancon and Bailey show in Beantown. 

    Cherington got Houston closer Mark Melancon in a deal a few weeks ago. And yesterday, he pulled the trigger on a deal that sent Josh Reddick, who was in the running for the vacant right field position, along with two prospects, Miles Head and Raul Alcantra, to Oakland for their closer, Andrew Bailey, as well as reserve outfielder Ryan Sweeney. 

    As of now, Melancon figures to be the eighth inning set-up man, and Bailey will close. 

    On the surface, this deal appears to dramatically favor the Boston Red Sox. After all, Bailey is a young closer signed to an affordable contract through the year 2015. He had a subpar 2011, but he was also hampered by injury. 

    Melancon is cheaper and younger and figures to set up and work the eighth inning. 

    Who wins and who loses in the deal that went down just before 5 p.m. EST yesterday?

Andrew Bailey: Winner

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    If you're a competitor, then you want to play for a team that's dedicated to winning. 

    The Oakland A's are currently dedicated to rebuilding. 

    The Boston Red Sox are going to enter 2012 as one of the American League's more competitive teams. Andrew Bailey makes them that much more competitive.

    Bailey will go from playing before sparse Oakland crowds to sold-out Boston ones. He'll have more save opportunities, and the games that he gets to close will be of greater consequence. 

    Closers tend to thrive on the electricity of the moment, and as Bailey said yesterday when asked about the chance to close for the Red Sox: 

    There's nothing like the atmosphere of running in from the bullpen at Fenway Park. You can't put it into words. It's something I look forward to doing day in and day out in a Red Sox uniform. Fenway is the greatest stadium in baseball, and to be able to pitch in that uniform and in that stadium is something I'll never forget.

    That sounds a lot like a guy who feels like he comes out a winner in this trade. 

Ben Cherington: Winner

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    For new Red Sox general manager Ben Cherington, it hasn't been the smoothest transition. 

    He arrived on the job at a tumultuous time in Red Sox history, taking the reins from decorated former general manager Theo Epstein whose departure had been controversial.

    Cherington inherited a Red Sox team that had just completed a spectacular regular-season collapse. He also had to hire a new manager to replace two-time World Series winner Terry Francona, who had left the team.  

    When the search for a new manager took longer than anticipated, many thought that Cherington  was being treated like some sort of figurehead by those above him.

    Even after the hiring of Bobby Valentine, it was tough for Red Sox fans to sit idly by while other teams snatched up high-profile free agents with the Red Sox merely spectators. 

    Today's trade changes that, though. 

    Andrew Bailey is a proven closer. He's been an All-Star twice and won the American League Rookie of the Year in 2009.

    Better still, Cherington didn't have to part with any of the organization's top prospects. This was a true score for Cherington.

    Jon Heyman of CBS Sports referred to it as Cherington's "finest moment" in a column last night. I couldn't agree more. 

Josh Reddick: Winner and Loser?

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    Can you be both a "winner" and a "loser" in one trade? 

    You might want to ask Josh Reddick that. 

    After all, it's every major league prospect's dream to get a starting job in the majors, and as a result of yesterday's trade, Josh Reddick has an excellent chance of doing just that next year. There's a very good chance that Reddick will start in Oakland.

    That's the good news; you're a starting outfielder in the majors. 

    It is in Oakland, though. 

    There's nothing wrong with Oakland. There are far worse cities to play in. The Bay Area is beautiful. The team has a decorated history: Vida Blue, Reggie Jackson, Catfish Hunter, Rickey Henderson, Dave Stewart, Jose Canseco, Dennis Eckersley, Miguel Tejada, Jason Giambi, etc, etc. 

    There's not going to be much suspense next season, though. Oakland will finish third or, more likely, fourth in the American League West. 

    Reddick will get a chance to prove he's a viable every-day major league outfielder, but it won't be before sold-out, passionate Fenway crowds. 

    With this deal, Reddick won an opportunity he may not have gotten in Boston, but he also will miss out on the pennant races and the passion of Boston and its fans. 

Ryan Sweeney: Loser and Winner?

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    On the morning of Wednesday, Dec. 28, 2011 Ryan Sweeney had a pretty good shot at starting in the outfield for the Oakland A's in 2012. 

    Twenty-four hours later, he's probably a backup again. 

    He's a backup in Boston, though. Sweeney is sort of the opposite of Reddick. His ability to showcase his own individual talents is not what it was when he was in Oakland, but his chances of playing in the postseason and winning the division, pennant or even more are all better as of now. 

    Sweeney has battled injuries, but he's always hit in Oakland. He's not a base-stealer or a home-run hitter, so he's never gotten a ton of press, but he's a solid and dependable backup outfielder. 

    That's not to say that Sweeney can't start in Boston, but it doesn't seem unlikely.

    If Ryan Sweeney was happy as a backup in Oakland, then he'll probably be thrilled to play that role in Boston.  

Red Sox Farm System: Loser

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    The Red Sox may not have given up their top prospects in this trade, but make no mistake about it. The Red Sox farm system is weaker today than it was yesterday, and that's because of the trade for Andrew Bailey. 

    No one gets anything for free, so the Red Sox knew they'd have to part with someone they liked to acquire Bailey. 

    Miles Head and Raul Alcantra aren't the first names most Red Sox fans think about when they envision future stars at Fenway, but they're not guys that lack potential. 

    Head is a 21-year-old right-handed hitting first base prospect who mashed 22 home runs while driving in 82 runs at single-A ball last season. He also hit .299 as well.

    Maybe Head is a future big-leaguer, but where is he going to play in Boston? With Adrian Gonzalez locked in for the next seven years, the first base spot is a little crowded, so the Red Sox were probably smart to "sell high" on Head. 

    Alcantra may be a guy that Red Sox fans wish they had back down the road. It's just too soon to tell. Alcantra is only 19 years old, and he was lights out in the very low minors last season. He eventually got to low-A ball, and there, he hit a bit of a wall. But at only 19, a team can afford to be patient.

    It might be several years before Boston fans can truly evaluate this deal, but even with all the unknowns, the Red Sox farm system is definitely weaker today than it was pre-trade. 

Oakland Farm System: Winner

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    If you were of the opinion that Oakland had a good minor league system before the offseason started, then wait until the next set of rankings come out. 

    Oakland has now traded three major players from their big league team: Andrew Bailey, Gio Gonzalez and Trevor Cahill. All three trades brought primarily minor league talent to Oakland. Without counting, Josh Reddick, who is in all likelihood going to be a starting outfielder in Oakland next season, the A's netted nine prospects as a result of trading these three players. 

    Nine new minor leaguers, and some of them are very highly rated. Oakland's system is now flush with talent. All they need now is a stadium at the major league level to play in.