The Yankees Are the Most Underwhelming Team in Baseball: Where Do They Go From Here?
Every year the Yankees are expected to be World Series contenders and it's an entirely fair expectation. No other team in baseball can offer a richer tradition, more exciting city atmosphere, or the available resources that the Yankees have in New York. Yet somehow they haven't really been a viable threat to win the World Series since their last championship run in 2009.
This has been especially surprising since the 2017 season. That year, the team's new core of young players developed rapidly and surprisingly pushed the eventual champion Houston Astros to a game seven in the ALCS. It was unusual to see the Yankees as underdogs but as a young team on the rise, that was sure to be short-lived. Still, four full seasons have elapsed since that run and it remains the highwater mark for these Yankees. They've been a good team - winning at least 100 games in both 2018 and 2019 - but have done nothing to separate themselves from other good teams come October. So what's made the once big, bad Yankees such an underwhelming team?
Let's start with the front office's recent tendency to pinch pennies rather than use their financial might to improve their team. In this space last offseason I wrote the following: "They [the Yankees] can certainly contend for the AL East crown and have a good shot to at least sneak into the playoffs via a Wild Card spot. Yet there's no denying they could have done a lot more thus far this offseason to increase their chances."
While they did sneak into the playoffs as a Wild Card, it actually took some significant roster re-tooling at the trade deadline to get them there. That simply shouldn't be the case when they clearly had the resources to improve obvious areas of need before the season but refused to in order to stay under the luxury tax threshold and save a few bucks. What's the use of being the most valuable franchise in baseball if you don't use it to your advantage to put a better product on the field?
Nobody's going to feel bad for Yankee fans when the team doesn't go the extra financial mile. This is the same team that absorbed Giancarlo Stanton's $300+ million contract a few years ago and shelled out another $300+ million to acquire Gerrit Cole before the 2020 season. But consider what the Yankees spend on payroll as a function of what they're worth. They spent only around 3% of their franchise value on players in 2021, which sits in the bottom five in baseball, around the same level as the lowly Pirates and Orioles. For a franchise that has historically relied on large amounts of money to solve their problems, this philosophical switch to frugality means new, creative solutions are needed to get the team back to legitimate World Series contention.
That hasn't happened. Brian Cashman has proven quite adept at turning scrap-heap pick-ups into valuable major league players and re-building a flawed team on the fly as he did this year, but that's not enough. In the MLB today, the very best players rarely hit the open market. Most teams have wised up to the franchise-friendly salary structure that restricts what a player can make for the first six years of their career. Using that baseline, they can lock up a player long-term early and secure their prime years at a price far less than a player could get as a free agent (assuming they stay healthy).
The problem in New York is that they don't really get those opportunities. In the years since the late 90's dynasty, the Yankees organization has developed two superstars - Robinson Cano and Aaron Judge - and one rock solid everyday player in Brett Gardner. A yield of three quality players over the span of more than two decades is impossibly bad. And in the case of Judge, it's clear that the front office still hasn't wised up with the rest of the league and locked in their franchise player long-term while they're young. With Judge due to be a free agent after next season, the Yankees are poised to low-ball him and unnecessarily let negotiations drag on as they did with DJ LeMahieu last year.
A lot of the responsibility for the underwhelming nature of the current Yankees is on Cashman. Sure, the penny-pinching mandates come from the top, but as the person ultimately responsible for putting a winning team on the field, he's failed to give the Yankees a fertile player pipeline which would lessen the blow of a tighter payroll. There could be many factors contributing to this failure. For example - poor scouting, a player development staff that doesn't effectively get through to young players, an ineffective strength and conditioning program. Wherever the issues may lie organizationally, Cashman hasn't identified them accurately and/or been able to fix them for many years now.
There's a strong stable of Yankee fans that also point to Aaron Boone as part of the problem, and feel that retaining him was a mistake. There's certainly some truth to Boone being an imperfect manager, but replacing him wouldn't mean much without significant changes elsewhere for the Yankees. As an on-field tactician he doesn't set the world on fire, but the same could be said of Joe Torre. That didn't seem to stop Torre from having a heap of success in New York in the 90's. The difference is that Torre inherited a team filled with major league ready youngsters and a front office willing to spend to win. Boone inherited a team centered around players embarking on their major league careers still with some fundamental flaws and ownership that had no back-up plan if those players didn't work out. So if Boone isn't the root cause of the Yankees' issues should Cashman be the odd man out?
Not exactly. As previously noted, Cashman is a shrewd negotiator when it comes to managing the roster. Whether it's dealing pending free agents for talented prospects, acquiring stars near the trade deadline without sacrificing his own top talent, or identifying other teams' cast-offs as useful players, he has mastered the art of the deal. Cashman should stick around and continue to work his magic, but perhaps his role can be scaled back a bit to just that. When it comes to management of the Yankee farm system, it's clear that someone who can complement Cashman's strengths needs to step in and overhaul what's broken.
Tim Naehring has been the Yankees' Vice President of Baseball Operations since 2015. Working closely with him are long-time scouting director Damon Oppenheimer and Kevin Reese, who has handled player development since 2017. Considering how this triumvirate handled to the group of Baby Bombers that seemed so promising during that 2017 run, I'd say it's time for them to go and a have a new group with a fresh perspective come in to turn the organization around from the bottom up.
Of course, the Steinbrenner head of the Yankee monster could help significantly by leveraging their obvious financial advantage over the rest of the league. There's very little chance of that happening, which leaves the scouting/development reset approach as the only viable option for a bright Yankee future. In Cash we trust, he just needs to be humble enough to off-load part of his responsibilities to someone who can focus on cultivating a winning culture starting at the lowest levels of the farm system. Anybody know a guy like that?
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