Brian Cashman always makes the Yankees a winning team

Since Brian Cashman was hired by the Yankees 19 seasons ago, New York has been weighing his collective successes and failures nonstop, debating the value he brings with the fire of a thousand takes. Cashman’s resume now includes four World Series titles and an incredible streak I’ll get to in a bit, so labeling him anything other than an excellent general manager is absurd, but given the massive stage and vast resources at hand, there’s been pressure on Cashman since day one.

The gravity of Cashman’s job may be minor in the grand scheme of life, but for many New Yorkers, his decisions can feel like life or death situations. The importance placed on winning in the big apple is quite possibly unparalleled, but luckily for Cashman, he’s done quite the job in that department.

The most basic goal for any team, aside from winning a World Series, has to be to win more than they lose, because, well, that’s how a team wins the championship, when push comes to shove. Luckily for Cashman, he’s done exactly that for as long as he’s been at the helm: since taking over as the team’s GM, Cashman hasn’t let his club have a losing season. That’s 19 seasons of over .500 ball, the longest such active streak and second best in the history of the game, behind only the incomparable dominance of the Yankees from 1926-1964.

As impressive as this streak is, it’s almost a necessity for a team like the Yankees. Based in perhaps the largest sports market in the world, the spotlight has been, and always will be, right on Yankee Stadium, and the over-reactive New York crowd will always be ready to pounce on the slightest misstep. Hell, we’re talking about a team who hasn’t won a World Series in seven years, and is now apparently amidst a “title drought.”

The onus for any Yankees struggles would be immediately placed on Cashman, the orchestrator of the potentially wallowing roster, so for his own sake, and for everyone working under him, winning, no matter the obstacles in the way, was more of an expectation than a success.

Unquestionably, this streak of winning ball is a huge accomplishment for the Yankees, but it’s come at a cost. Calls for a rebuild by the Yankees have been growing for the past half-decade or so, and many of these pleas have legitimate points. The Yankees have made the playoffs just once over the past four seasons—they didn’t win a game in that one postseason appearance—and the team’s aging and costly roster was getting nowhere. Had the Yankees been in a vacuum, without ownership or the media expecting wins and excitement on the field, a full-blown rebuild would’ve been the most popular option among beat writers and, likely, Cashman himself.

The byproduct of a rebuild is multiple losing seasons, though, so Cashman instead was forced to try and win with an ugly roster in an unenviable situation. The stagnant team had gotten nowhere from 2015 to the first half of 2016, and it looked like Cashman had simply delayed the inevitable, with the on-field product suffering for a few years extra as a result.

The genius of Cashman has managed to create a two-month-long rebuild, restocking the farm system while sparing fans of multiple seasons at the bottom of the league, but with the benefit of hindsight, accepting those losing years (instead of scraping to remain above .500) would’ve been the best choice. The Yankees probably wouldn’t be saddled with some less-than-optimal contracts, most notably Chase Headley and Jacoby Ellsbury’s, had they opted to rebuild sooner. Alas, Cashman was forced to wait until the last possible moment because of that winning expectation.

The Yankees finally dove headfirst into a rebuild at last year’s trade deadline, yet they may somehow avoid the losing associated with that. The Baby Bombers managed to go 40-34 in the second half despite selling off several major big league pieces, and nearly found a way to make it to the playoffs. Given the additions of Aroldis Chapman, Matt Holliday, Greg Bird, and Chris Carter to this year’s Yankees, along with some potentially impact prospect promotions, there’s cause for optimism. While the club may not make the playoffs the year following a large-scale rebuild, it’s hard to bet against the Yankees winning more games than they lose, for the 20^th straight season under Brian Cashman.