It’s been 17 years since the New York Yankees tasted the top of the baseball world. The team had an aging but strong roster, featuring Derek Jeter, Bobby Abreu, Andy Pettitte, CC Sabathia, and Mark Teixeira, to name a few. Since then, the team has gone through painful playoff exits and lackluster seasons, filled with signings that don’t pan out or prospects that bust hard.
Yes, the team has gotten star players that have panned out well, including Max Fried and Cody Bellinger. There is a cluster of other signings or trades that don’t work out, including the Juan Soto trade they couldn’t capitalize on, and the Giancarlo Stanton trade, where he continues to get hurt. They can’t seem to either get the best value out of them or keep them within a few years, losing them to another team. The worst part is that the team refuses to build around these signings when they are in pinstripes. What’s the point of keeping prospects or star players if the results don’t change?
It might be time for the Yankees to do something drastic to win again: Rebuild their whole roster or their farm system from the top down.
The old-time Yankees built their dynasty in the late 1990s through two avenues. The first avenue was developing their prospects to All-Star status under the leadership of Brian Sabean and Bill Livesley. Both of them are credited with building the “core four” of the Yankees’ 1990s dynasty. The one thing they wanted to do was “get away from average” and hone in on one special tool a player could have.
With George Steinbrenner at the helm, along with his impulsive spending and trading habits that netted Tino Martinez, Paul O’Neill, and Scott Brosius, the Yankees kept winning.
Things began to change in 2005, when Damon Oppenheimer became the head scout. It appeared the team had begun to aim for “just good enough” instead of one-tool talent in their drafts, as evidenced by their lackluster draft classes between 2005 and 2015. Things declined even further after George died in 2010 and the subsequent ownership under Hal Steinbrenner, exacerbated by high-profile retirements.
The team began to rely heavily on aging veterans rather than young talent, as evidenced by their brutally old roster in 2013, hosting Lyle Overbay and a 39-year-old Ichiro Suzuki. That theme is still somewhat present today, with their top three pitchers, Gerrit Cole, Fried, and Carlos Rodon, all over 30, and Aaron Judge pushing 35.
Even with their young players, a lot of them are not panning out. Anthony Volpe hasn’t had a single season with an OPS over .700, Jasson Dominguez has yet to find his footing, and Will Warren remains inconsistent. They do have Cam Schlitter and Ben Rice, which helps them a lot.
But if the team isn’t improving, there’s a chance the New York Yankees should look at selling off.
If the New York Yankees want to think about winning a championship or getting back to their former glory, they might have to look past their current roster makeup. In fact, they might have to consider tearing parts of it down for future pieces. That might come with their first losing record in over 30 years, but the team needs a hard reset if it ever wants to see a World Series championship again.
The first strategy they could pursue is to sell off some of their younger pieces to reinvigorate their farm system. Following the MLB draft earlier in July, the Yankees farm system ranks 15th in the league, ranking slightly higher than at the start of the season. Outside of George Lombard Jr., however, there’s not deep talent except for Carlos Lagrange or an up-and-coming Dax Kilby.
What the team does have are pieces they can move at the deadline or at the end of the season. The aforementioned Rice, although cooling down from a hot start, still has a respectable .931 OPS and 31 home runs. Austin Wells, their lone startable catcher, might also need a fresh start after struggling in New York. Warren could also net a trade or two, given he has years of team control until the 2030s.
Don’t expect the team to sell off Schlittler or Fried, however, because they’re two pillars in a potential rebuilding situation.
The second strategy for the team would be to trade away parts of their farm system for big-time talent while breaking their budget. Depending on the outcome of the ongoing Collective Bargaining Agreement discussions, the team has to be smart with who they get and what they want.
It might not be wise for the New York Yankees to trade away Lombard Jr., given that the team is not stable in the middle of the infield with Jazz Chisholm Jr. in his last year of arbitration. Volpe and Jose Caballero are currently in a revolving door at shortstop, and Ryan McMahon still hasn’t figured out the mystery behind hitting.
The good news is that the Yankees have four top-100 prospects, including Kilby and Elmer Rodriguez, who might net a return. They could also headline a big trade for any players on the market. It’s a bit of a weak market in 2026 outside of Tarik Skubal, but the team could look for Zach Neto or Tyler Stephenson to plug critical holes in their offense.
The New York Yankees are supposed to be known for winning championships or being in contention. Over the last two decades, it feels like they’ve barely been existing in the American League East. For a team with such a storied legacy, it’s unusual for them to be this mediocre for this long.
Again, with a fanbase growing restless and critical of ownership, it might be time for the team to make moves they usually don’t make. It might be moves that could stun or shake the fanbase, but given where ownership wants to go, it might just pay off in years.
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