Another winter has passed with Hal Steinbrenner inching his way towards the edge, dipping his toes in the all-in pool, and quickly tiptoeing backwards after the jolt of the cold water shot up his leg.
The Yankees began the offseason with authority, swinging a blockbuster trade for Juan Soto and solving their righty-heavy lineup woes by adding one of the best lefty bats in the game. In terms of filling a need, the Yanks couldn’t have found a better solution.
But those same Bombers, who finished with just 82 wins in 2023, aren’t a team with just one need.
An all-in season implies addressing every need and entering spring with as few roster holes as possible. Once again, Steinbrenner seemed willing to plug one hole and try to sail out to sea with a few leaks. Sure, Soto himself solves glaring deficiencies with the Yankee offense, and gives them arguably the best hitting duo in the game along with Aaron Judge, but this team has other concerns, ones that could have been addressed this winter. As the winter winds down, those needs are still glaring.
The rotation behind Gerrit Cole was in shambles for much of 2023. Nestor Cortes, coming off an All-Star season that also included a career-high workload, battled multiple injuries and will be coming off shoulder surgery when he reports to camp next week. Carlos Rodon battled injuries of his own and was all-around terrible in his debut season in pinstripes. Clarke Schmidt was a fine No. 5, but will be coming off his highest workload in a season since he was in college.
Signing Marcus Stroman to a team-friendly deal isn’t enough to wipe your hands and move on to the next problem.
Stroman is a solid signing (especially at that price), but doesn’t account for four question marks behind Cole. The Yankees still needed another starter, and one of the best in the game was available via trade in Corbin Burnes, who is now with a divisional rival. The reigning Cy Young winner in the National League, Blake Snell, is still unsigned, but the Yankees seem to have kicked their feet up on the rest of this offseason. It’s an all-too familiar, and destructive, game plan.
Let’s go back to the only security blanket in the Yankees rotation. Gerrit Cole, who was signed after the Yankees fell in excruciating fashion to Cole’s Astros in 2019, seemed like an all-in move at $324 million, as the Yanks looked to finally get past Houston and back to a World Series. Still, there were questions in the rest of the rotation. Could James Paxton avoid injury despite dealing with several over his career (he couldn’t)? Would Jordan Montgomery be ready coming back from Tommy John surgery (he pitched to a 5.11 ERA in 2020)?
Starting pitching aside from Cole, unsurprisingly, became an issue in the playoffs, leading to the infamous game two attempt of using Deivi Garcia as an opener in the ALDS. Two winters later, the Yanks passed on the likes of Corey Seager and instead added Isiah Kiner-Falefa and the corpse of Josh Donaldson. The next offseason, Aaron Judge and Carlos Rodon were signed to big-money deals, but left field was still a massive hole, and third base was far from secure after an awful season from Donaldson. Left field became a black hole all year, and Donaldson was eventually cut.
So, as this offseason nears a close, the Yankees once again seem to be stumbling into their chronic shortcoming: taking a step towards going all in, towards breaking for a mad dash home, only to shuffle back towards the safety of third base at the slightest sign of movement from the pitcher. Trading for Soto and signing him to a record arbitration-eligible payday is nothing to scoff at, nor is signing Judge to a $360 million deal or Cole for $324. Steinbrenner and the Yankees clearly spend, but it’s the subsequent spending that is necessary, the other big moves to show that the organization isn’t playing around. It’s signing Mark Teixeira after introducing CC Sabathia. It’s trading for Roger Clemens after a 125-win season. Not heading into spring with multiple needs that you hope can be addressed at the trade deadline, or from within.
The Yankees got better this winter. That is without question. But for another offseason, there are real questions about whether they got better enough to be a true contender, and those questions could have been squashed with another all-in move or two. Instead, the Yanks retreated after flirting with a plunge into that all-in pool.


