"Jordan, we didn't think you belonged in the Yankees' postseason rotation. Then you won a World Series elsewhere. We traded you out of town the day after your wife landed in New York for the next step of her medical schooling journey. We made you drop everything and pick up the pieces. We didn't give you a heads up. We claimed to have acted with forethought, but actually things came together pretty quickly and we didn't think much of you. We'd now like to offer you $160 million, which is about $60 million more than you would've cost if we'd believed in you last summer. Now, how could you refuse us, your best friends?"
If you struggled through that hypothetical Brian Cashman sales pitch to Jordan Montgomery, you're not alone. If you tried to distill that message into more palatable terms, best of luck. It's pretty unpalatable, any way you slice it. And that's why, while MLB insider Ken Rosenthal's pitch of Montgomery as a Yoshinobu Yamamoto backup plan in the Bronx is noble, it just doesn't sound feasible.
The latest claim is that the Yankees have "internally" discussed the option. It certainly feels like that internal discussion would've come to a conclusion very quickly, "Yeah, uh, we bungled this one in 2022, though, right? Next. Anybody got Imanaga scouting reports?"
Yankees probably won't sign Jordan Montgomery despite 'internal' discussions
"Hey, Jordan. You rightfully hate us and we've made it clear you were our No. 2. Let's dance?" Not a winning strategy.
While a Montgomery reunion might be a holiday heartwarmer, it's about as likely as the Yankees re-signing Roger Maris. The far more noteworthy portion of Rosenthal's latest column was the suggestion that the Yankees had no plans to stop beefing up their pitching staff, Yamamoto or no Yamamoto.
There is the very slight possibility of a large deal for Montgomery, sure, but there's also the chance Hal Steinbrenner grabs Frankie Montas and hits the trade market for Shane Bieber, Dylan Cease or Corbin Burnes. He might also authorize the construction of a "super bullpen" featuring Robert Stephenson and Jordan Hicks. As Yamamoto's price climbs, dabbling elsewhere becomes dicier, but Steinbrenner cannot yield. This team needs a frontline 25-year-old starter. Of course they do. But they also need depth. And while spending on the 'pen feels unlikely, considering how often this team seems to cobble together relief aces out of nowhere, it's still comforting to hear they remain deadly serious and won't consider their pitching chase over, even if the market's hottest name chooses their offer.
But Montgomery? Maybe if a similar lefty with less history emerged. But Rosenthal's reported "internal discussions" more than likely hit a dead end.