"I'm not sure I'm going to be able to make a deal," he confided.
Teams sensed the desperation in the Bronx. Their asking price was exponentially high. Cashman vowed not to be fleeced.
The bidding and trading ended Wednesday just as Cashman envisioned. He made no move to bolster the starting rotation. He was either resolute or stubborn, disciplined or just plain blind to the possibility of an October wipeout. You choose the assessment.
But here's the question that now hangs over Cashman like a guillotine: has he left the Yankees defenseless? In a year they're on pace to win 103 games, did he blow it by not being bold enough?
We'll find out soon enough, but the optics are terrible in the meantime.
The Astros, not the Yankees, were able to pull off a dramatic 11th-hour deal to acquire Zack Greinke. For the second time in three years, Houston made the type of deadline swap that presented a change in the balance of power.
In 2017, the Astros swooped in for ace Justin Verlander, who promptly took them to the World Series. The Yankees had the same opportunity to trade with the Tigers, but owner Hal Steinbrenner vetoed negotiations, as he didn't want to crash through the luxury-tax threshold.
This time, Cashman wasn't constrained by money as much as a fierce attachment to his prospects. Up until the last minute Wednesday, he guarded 20-year-old Deivi Garcia, the franchise's prized possession, who's currently at Triple-A.
According to one major league executive, the Yankees were in serious talks to acquire Marcus Stroman—not from the Blue Jays, but from the Mets, who were prepared to flip the right-hander to the Bronx in exchange for Garcia and outfielder Estevan Florial, among others.
The Yankees flatly said no. They were willing to consider a deal with one of those prospects, but not both.
The steadfast belief in developing young talent has been a hallmark of Cashman's tenure, which is a complete reversal of how the Yankees used to do business. The laser focus on the future has won Cashman praise throughout the industry.
But that still doesn't address the gaping hole at the front of the Yankees' 2019 rotation. Yankees starters rank last in the American League with a 7.65 ERA since the All-Star break.
While assessing the Yankees' starters, one talent evaluator said: "There isn't one guy who I'd have confidence could beat Verlander or [Gerrit] Cole when it really counted. The Yankees have some fine pitchers, but if you're talking about a lockdown ace—no."
Masahiro Tanaka has been wildly inconsistent throughout his career, and he admits he's lost the feel for his signature splitter because of the baseball's lowered seams this year. James Paxton and J.A. Happ are suffering from Sonny Gray Syndrome: talented but uncomfortable in the Bronx. CC Sabathia is at the end of his career, currently on the IL (again) with knee problems. And Domingo German, who has been surprisingly effective for most of the year, has never pitched in the postseason.
Cashman's plan B has been ready all along: a healthy and restored Luis Severino, who's supposed to pitch himself into shape in the final two months of the season. Along with Dellin Betances, who's expected to rejoin the bullpen later in August, the Yankees are hoping the in-house additions will make up for the empty trading season.
And Garcia? He'll be in the Bronx in September to allow the other starters to skip turns and otherwise prepare for the postseason.
This plan has merit. It could bear fruit. But Severino, who's recovering from shoulder and lat issues, hasn't thrown an inning all year. Handing him the ball with the expectation that he'll rescue the Yankees, not to mention allow Cashman to save face, is an awfully big ask.
The trouble is, there are no other options. Cashman couldn't pry Trevor Bauer away from the Indians or Madison Bumgarner away from the Giants. He lost out on Stroman when the Jays jacked up the price, and he wasn't about to come crawling to the Mets.
Cashman, in fact, said he had no problem walking away from all of these deals. He still believes the Yankees have the talent to prevail. Now he's on the hot seat to justify that faith.
Another executive took issue with the Yankees' approach. Although he praised Cashman for his efforts to strengthen and deepen the farm system, he thought it should've been a secondary agenda to what matters most—winning championships.
"Sometimes you have to go off course by a couple of degrees to get it done," the executive said.
The point is that Cashman needed to be bold, even if meant suffering some short-term pain.
The GM now has to answer to the ticket-buyers—not to mention the players in his own clubhouse—the most searing question of all: Did he do everything possible to make the Yankees better for the stretch run?