On July 14, two weeks in advance of the 2016 MLB Trading Deadline, the Boston Red Sox acquired All Star left hander Drew Pomeranz for top pitching prospect Anderson Espinoza. Much has been written about the magnitude of the deal for both sides; Boston got the top starting pitcher they wanted for this year’s postseason run (not to mention two additional years of team control), while the rebuilding Padres added a crown jewel to their farm system in the 18 year old Espinoza. However, it would be remiss to ignore the effect this deal will have on the trade market for the remainder of this July.

In this expensive free agency era of baseball, teams place immense value on prospects years away from the big league level because they are potentially an affordable commodity. Cost controlled assets like Anderson Espinoza who are under team control for up to six years after making his (presumed) major league debut are invaluable to a team unable to sign a proven veteran such as Zack Greinke to a six year deal worth 206M. Traditionally, top prospects have been used as blue chips to trade for a big league star (often at the end of his contract) – a win now move. However, even teams that wish to contend this year such as the Chicago Cubs or Texas Rangers are less inclined to part with top prospects for what could be their desired “final piece” for a potential championship team. Typically, an established player is at or near the end of his contract, meaning a team would be acquiring the player for two or three months. These “rental” players lose value for the duration left on their deal, and teams are reluctant to relinquish cost controlled assets in a trade.

The New York Yankees of 2016 find themselves in a position that they have not experienced in well over twenty years – a team with no chance to contend. As they prepare to become “sellers” in this year’s trade market, their goal is to turn their current major league assets into blue chip prospects. This rebuilding process is easier said than done, as their two most obvious assets are considered “rental players” in OF/DH Carlos Beltran and southpaw closer Aroldis Chapman. Among their most sought after pieces is 2015 Mariano Rivera AL Reliever of the Year Award winner Andrew Miller, who is under team control through 2018 for 18M; however, the Yankees would have to receive a “Godfather” offer to consider moving him. That leaves Beltran and Chapman as the two prime chips for New York to deal. 

The Chicago Cubs are 55-36 (as of July 18) and already eight games ahead in the standings. They have one of the strongest cores in baseball, arguably the strongest farm system, and a dire need for left handed relief pitching. After reaching the 2015 NLCS, they are poised to make another deep playoff run and acquire the final piece to get there. With the contending Chicago in need of left handed pitching and the rebuilding Yankees with left handed pitching to spare, even the dimmest of baseball pundits can make the connection that the two teams match up favorably in a trade. Unfortunately for them, the task of formulating a realistic package is difficult considering Chapman is a rental. Many speculate that the Cubs would have to part with C/OF Kyle Schwarber in a deal for Andrew Miller – Theo Epstein himself has declared Schwarber untouchable. After getting by that fantasy, the grim reality for New York is that the pending free agent Chapman will not garner one of the Cubs coveted top prospects. The market simply was not in the Yankees’ favor – until July 14.

When the Boston Red Sox entered trade negotiations with the San Diego Padres for Drew Pomeranz, it was clear that the price for a young All Star under team control would cost one of Boston’s prized prospects. Rather than holding onto Espinoza and targeting a lesser pitcher than Pomeranz, Dave Dombrowski went “all in” for the sake of contending in the present. This bold move changes the market because now the seemingly out of bounds prospects become fair play. Brian Cashman can tell Theo Epstein in Chapman negotiations that Boston paid the price to contend, and therefore he must as well. Epstein certainly does not want to see Chapman traded to a rival like San Francisco or Washington, so the Yankees have gained leverage thanks to Dombrowski. Kyle Schwarber is still a pipe dream for the Yankees brass, but tides have certainly turned.

One outside the box idea is to package Chapman and Beltran in the same deal. The Cubs outfield has seen Schwarber go down for the year, Jason Heyward and Jorge Soler struggle, and Dexter Fowler deal with injuries. Although Carlos Beltran is best suited as a DH at this point in his career, his undeniable consistency with the bat can justify him as the answer to solidify the Cubs’ outfield. By including Beltran with Chapman, the Yankees would be reasonable to ask for one of the Cubs’ coveted prospects (in the Espinoza mold). One who would be a good fit is 2B/OF Ian Happ, who in AA is close to the majors and has shown 20/20 potential. Another target could be top prospect Gleyber Torres, a shortstop praised for his all around tools. With Happ or Torres as the centerpiece the Yankees require, the deal could be filled out with one more “B level” prospect in the Cubs system – 1B/DH Dan Vogelbach (good power but limited defense and blocked by Anthony Rizzo) or OF Billy McKinney (athletic contact hitter but little power) are talented prospects with their own question marks that the Cubs could part with.

Dave Dombrowski is an executive that possesses more gumption than most. For every one of his colleagues, the standard has been set. He dealt a pitcher that could be a superstar down the road for a chance to win now, and still owns the second strongest farm system in baseball.

The 55-36 Cubs own the first.