The MLB trade deadline is crunch time for all GMs and baseball execs, some more than others. Here are the five front-office staffs with the most to prove in the next two weeks.
1. Hal Steinbrenner and Brian Cashman, New York Yankees
The last time the Yankees were true sellers at the trade deadline was in 1989, when they jettisoned superstar Rickey Henderson to the Oakland Athletics for outfielder Luis Polonia and relief pitchers Greg Cadaret and Eric Plunk. Yankees owner Hal Steinbrenner was still a teenager (19) at the time. Hal and his brother Hank inherited the team when their father George M. Steinbrenner passed in 2010, and the Yankees have remained in buyers mode since then.
As of today, Steinbrenner has GM Brian Cashman and the baseball operations department prepared to either buy or sell, based on how the team does in the coming days. But in my mind, the correct approach would be to sell, regardless of how the team does. Why? For both business and baseball reasons. Business-wise, it's a sellers' market, and there aren't many sellers with significant assets. The Yankees can take advantage of this by dangling two of the best left-handed relievers in the game in Aroldis Chapman and Andrew Miller, as well as veteran outfielder Carlos Beltran.
Baseball-wise, contending teams already are lining up for Miller, Chapman and Beltran, and the Yankees could end up getting 4-6 significant prospects back for the trio (in separate deals), which would dramatically help them rebuild for 2017 and beyond. Also, the free-agent market is going to be thin outside of a few bats, so trading now is the best way to improve quickly. The Yankees could always re-sign Chapman as a free agent in the offseason.
The Yankees have to be concerned with the strength of the Red Sox and Orioles both short and long term; they need to do something. Other than injured first baseman Greg Bird and outfield prospect Aaron Judge, the Yankees are pretty thin at the upper levels of their farm system, and trading for talent is the only way to improve it.
Cashman has never been a seller at the deadline, and Steinbrenner has never ordered his GM to be one. Now is the time to flip the approach and work some magic.