The question surprised me at first. To say the least.
“Why,” a scout from a contending National League team asked in late July, “are the Yankees making Bellinger available?”
Huh?
And why, the scout went on to ask, were they making it known that they would talk about Devin Williams, Luke Weaver and Trent Grisham, all free-agents-to-be?
When we dug into this with our Yankees sources, it proved true. With the team playing poorly and Aaron Judge facing possible Tommy John surgery, Brian Cashman and staff were in the preliminary stages of considering pivoting to a sale.
I don’t want to overstate this. It never got as far as in 2016, when the Yankees were fully prepared to both buy and sell before choosing the latter. This was more of a thought about selling, followed by the decision to buy in a purposeful but measured way.
Now the Yankees are as confident as anyone heading into the postseason and still fighting to win the American League East. It’s worth remembering how far they traveled to get here — and how they achieved it by threading the extremely tricky needle of adding to the roster without sacrificing top prospects. It might go down as one of Cashman’s best tricks.
Deadline season began with a more traditional all-in mentality. On July 9, with the team 50-41, Cashman said, “We’re going to go to town. We’re going to do everything we possibly can to improve ourselves and try to match up.”
For most of the month, the Yankees treaded water at around ten games over .500, but played sloppily and lost too many games to good teams. Leadership was no longer convinced that this was a roster worth the sacrifice in prospects.
Then came the Judge scare. During a period of a few days that ended on July 26, the superstar underwent testing on his right elbow. The Yankees feared that he would need season-ending UCL surgery. Had that occurred, the Yankees might indeed have sold, sources say. They certainly would not have added in an aggressive way.
When Judge learned that he had a flexor strain and would return, Cashman and Co. landed in a middle ground.
They didn’t see it as an all-in year in the way that, say, the team’s only season with Juan Soto did. In that scenario, you focus almost exclusively on the present.
Still, the Yankees knew that their remaining schedule was relatively soft, and their team talented. They began to think of ways to improve the current club without damaging the future too much.
That included concepts that would have moved one big leaguer for another. One example, according to league sources, was a discussion with the Mets about dealing Trent Grishman for Brett Baty. The Mets needed a rental center fielder, while the Yankees sought a controllable third baseman and liked Baty’s lefty swing.
Obviously, that one never progressed. The Yankees addressed third base by acquiring Ryan McMahon from Colorado and continued to eye reasonably priced upgrades, with a particular interest in relievers and right-handed bench players.
On the day before the deadline, the Mets gave the Yankees a scare by paying more than the Yankees were willing for Tyler Rogers and Ryan Helsley. The Yanks had spoken to the Giants and Cardinals, respectively, about those players, and were not comfortable with the prices.
Once the Mets went there, the Yankees thought that bullpen help might not be attainable this year. But on deadline day itself, prices became more reasonable.
The Yankees were able to acquire closer David Bednar (a home run), Camilo Doval (a project with upside) and Jake Bird (since optioned to Triple-A), in addition to McMahon and bench pieces Jose Cabellero, Amed Rosario and Austin Slater. Not all of these players have helped, but taken together, those lifted the team’s floor.
Plus — and this might be the most impressive part going forward — the Yanks did not have to trade Cam Schlittler or top prospects like Spencer Jones, Carlos Legrange, Bryce Cunningham, Elmer Rodriguez-Cruz or Ben Hess. The desirability of that group also represents a player development success.
As a result, the Yankees find themselves competing for a championship this year, and anticipating a pitching staff in 2026 stuffed at various junctures with the likes of Gerrit Cole, Max Fried, Carlos Rodon, Schlittler, Lagrange, and Luis Gil, with the others knocking at the door.
Not a bad deadline for a front office that, just days earlier, didn’t know which way it should go. The next month will determine if it goes down in Yankee history. Come to think of it, the next few years will, too.
