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The Yankees’ risk-averse spending strategy has backfired

The New York front office has certainly spent money, but their series of half-measures has led to poor results.

MLB: Houston Astros at New York Yankees Wendell Cruz-USA TODAY Sports

One of the primary creeds to learn and deploy when operating a franchise in Major League Baseball (or really in most endeavors in life) is the following: It is ultimately shortsighted to close the door on certain paths for good, and flexibility is a positive thing.

This statement is sort of vague, so here is an easy and tangible example. For a while in the early “Moneyball” period, drafting college players was all the rage. Despite some rewards, there were enough missteps that the process somewhat trended back toward high schoolers. The reality is that drafting either can be a good investment; it really depends on an individual assessment of your board at any given pick.

I open with this idea to highlight that while the methods deployed by the Yankees in recent seasons have serious holes, it is not as though I mean to argue that this gambit will always be a poor one regardless of the situation. However, in the past few years the Yankees have been rather risk-averse, and since they’ve only paid for half-measure solutions, they’ve been hurt by a reluctance to go all-in on the game’s true top talents at the plate. This especially contrasts the team’s long history of adding superstars—or even just stars—to its lineup.

The only exception on this current team is Aaron Judge, who really doesn’t count, as he was retained even if he did reach free agency. The hard truth is that this team wasn’t in any condition to even contemplate the idea of letting Judge walk. A lineup that still looks bad with him would’ve been a complete laughingstock without the reigning AL MVP (who is now playing through injury and being pitched around).

The Yankees haven’t really been players in the deep end of the free-agent pool for hitters in quite a long time. Names like Manny Machado, Freddie Freeman, Bryce Harper, Corey Seager, and others reached the market. They were there for the taking, but any connections with the Bombers turned out to be slim at best. All without it ever getting close.

New York Yankees Introduce Mark Teixeira
Elite free agents like Mark Teixeira helped the Yankees win their last World Series title.
Photo by New York Yankees/Getty Images

Instead, this organization has relied on spending consciously—but spending nonetheless—on questionable players without as much long-term risk, but also without nearly as much of a short-term reward.

Josh Donaldson came over via trade and the Yankees took him on in addition to consecutive $25 million tax hits. To say nothing of the rest of the controversial trade, that might’ve been fine at another point in time, but despite manager Aaron Boone’s insistence otherwise, the aging former MVP was no longer the Donaldson we once knew from the moment he put on this uniform.

DJ LeMahieu offered another case of settling. He might have been coming off back-to-back top-five MVP finishes (the latter in a shortened 2020), but he was also an infielder nearing his mid-thirties. The problem wasn’t necessarily the Yankees guaranteeing him $90 million, as he fell off faster than anticipated and at the time, it wouldn’t have been stunning to see him remain productive for a few more years. The problem was that they signed him for six years with the sole purpose of reducing his AAV hit, believing that this was the true chess move. Now, they have a current 88 OPS+ bat under contract through the end of 2026.

The Yankees had already run afoul of this strategy with a guy who is no longer on the roster in Aaron Hicks. Once a savvy trade pickup, the team felt compelled to give him a seven-year, $70 million extension a year before he was set to reach free agency at age 30. They believed that if he followed his then-trajectory, they would potentially save a few bucks on the AAV. Unfortunately, this was still not the guy to bank on with any certainty to maintain his play, and they infamously cut him with over two years left on his deal.

When he was acquired, Giancarlo Stanton fit the aforementioned superstar bill, but we can’t pretend like adding him was a normal transaction. First and foremost, that was almost six years ago at this point and so much other top talent has hit the market and gone without coming to New York. Secondly, the Marlins threw $30 million into that trade and completely changed the outlook of his contract across those final three seasons. Stanton might be making a lot of money, but because of Miami’s help, his luxury tax hit is far from crippling at $22 million. Even in the offseason they made the splash to acquire him, they cut payroll.

Elsewhere on the trade market, the Yankees have opted for the likes of Andrew Benintendi, Joey Gallo, and Harrison Bader. All were capable of delivering decent production, but none were the highest-end names available on the market at those times.

In fact, let’s take another step back and look at the next-best thing on this team, outside of Aaron Judge: Gerrit Cole. We haven’t talked about pitching much, but the man received a hefty contract and has been worth every bit. Although it is doubtful that the Yankees let him leave, he could very well continue as he has onto next season, opt out, and the team would’ve never had to pay for a declining star down the line. Carlos Rodón hasn’t been great, but out of all the disappointments in 2023, he’s the one likeliest to bounce back next season, as long as he’s able to stay healthy. The stuff is still there.

To be clear, the rampant failures of this team could not and would have been all fixed by, “Hey, they should have signed more superstars.” However, once you take a moment to reflect, it’s easy to see the risk they assumed in risk-averse moves, and how it has backfired into paying an X-number of dollars in equivalent with a Y-value in production received from the majority of their lineup.

Most of the time when the Yankees have gone to the market, they’ve failed, and their last-place status reflects how many teams have passed them by through other winning strategies. The Yankees have always had financial might to fall back on, but they’ve refused to truly flex it.