The Chicago Cubs had the biggest offseason out of any team (John Lackey, Jason Heyward, Dexter Fowler, Ben Zobrist), and could follow that up with the biggest trade deadline. While the Cubs certainly have what it takes to get to October and go far into October, they know as well as anybody how key a big deadline move can be come Postseason. More often than not, the trades that bring in key bullpen arms are the ones that wind up leaving their mark in the postseason history books, so who better for the Cubs to get than Aroldis Chapman? The Chicago Cubs were one of a handful of teams interested in Chapman, and after reports said Washington and Cleveland were the front runners for the flame throwing closer, once again the Cubs snatched up a big name. The Yankees seemed to be extremely interested in the Cleveland Indians farm system, but Cleveland was wisely reluctant to give up one of their top prospects for a half season rental.
In return for Chapman, the Yankees received a haul of prospects, including Gleyber Torres, Billy McKinney, Rashad Crawford, and former Yankee bullpen member Adam Warren.
Gleyber Torres was the Cubs number one ranked prospect, and is ranked 24th on MLB.com's top 100 prospects list. Torres is expected to hit the Major Leagues in 2018, which means New York's Didi Gregorius' job is still safe for the time being.
Billy McKinney came to Chicago from Oakland in the deal that sent Jeff Samardzija and Jason Hammel to Oakland, and is now on the move again without cracking the major leagues. While McKinney is having a bad season in AA, he still has high potential and could pair well with Yankees outfield prospect Aaron Judge down the road. McKinney was the Cubs 5th ranked prospect and is 75th on MLB's top 100.
Adam Warren was a big piece of the Yankees bullpen for three years before being traded for Starlin Castro, a move that did not fair well for him
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Following two great season in New York (2014 - 2.97 ERA in 69 bullpen appearances. 2015 - 3.29 ERA in 43 games, 17 starts), Adam Warren was traded to Chicago along with a player to be named later in exchange for Starlin Castro. Things have not gone the same way in Chicago for Warren, as he posted a 5.91 ERA in 29 games (1 start) and was demoted to AAA twice. The Yankees could either use him to help their poor rotation, or stick him back in the 'pen with hopes of him returning to what he was with them.
Chicago has pushed themselves into a "must win now" corner with their aggressiveness
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Aggressiveness in the Free Agent or Trade market is certainly not a bad thing by any stretch, but it does throw you into some hot water if it doesn't work out. I have no doubt that the Cubs have one of the highest chances of winning the World Series this October, but as the Royals have proved big names and a big payroll is not always what wins it in the end. Should the Cubs not win the World Series, not only would they have given up big prospects for practically nothing, the repercussions could be huge. If the Cubs do not reach their World Series goal, Chapman would almost certainly walk (New York is already a huge front runner for him this Winter) and Jake Arrieta could follow Chapman's footsteps as well. While this move could be huge and you have to respect the Cubs willingness to take the risk to win now, if things blow up the Yankees may walk away with the landslide end of this trade. Chapman's performance is no question at all, because we know what he is capable of, but the Cubs now have more pressure than any team in recent memory to win the World Series, and win it now.