Projecting Yankees’ future Jordan Montgomery extension

New York Yankees left-hander Jordan Montgomery is a perfectly effective modern pitcher, and appears prepared to deliver above-average results for the remainder of his Yankee tenure.

With a theoretical non-dominant ceiling and a prominent lack of trust from management beyond a certain pitch count, though, will he be worth the next contract he ultimately receives? That might depend on whether the Yankees choose to prioritize an extension after 2022, or let him hit the open market after 2023.

Though all percentile rankings and traditional stats indicate that Montgomery, after undergoing Tommy John surgery in 2018, has leveled up, he’s still being treated with relative kid gloves by Aaron Boone.

In his six 2022 outings, fans have inexplicably seen him get built back down after reaching a pitch count high of 86 in Detroit three starts into his campaign. Since then, he hasn’t topped 71 pitches in three tries, despite great results:

• April 27 vs. Baltimore: 71 pitches, 5.2 innings, 2 earned runs, 4 strikeouts
• May 2 at Toronto: 65 pitches, 5.0 innings, 2 earned runs, 5 strikeouts
• May 8 vs. Texas: 71 pitches, 6.0 innings, 2 earned runs, 5 strikeouts

Montgomery starts have become nearly identical. He’s staked to a small lead, the Yankees fail to tack on, sometime around the sixth inning a run or two gets scratched across, and he’s not given free rein to make it to the finish line. Imagine if the Yankees had actually scored in any of his six starts.

Think about how your opinion of the left-hander would’ve changed. That is why they risk having to match a pricey second contract unless they act quickly … but have they shown any intention to do so? Instead, they’ll often yank him swiftly as if they believe him to be a late-game liability.

Projecting a contract extension for Yankees left-hander Jordan Montgomery

So, how would you go about projecting the next contract for the Yankees’ best homegrown left-hander since Andy Pettitte and Nestor Cortes Jr. (half-kidding)? It’s difficult. Right now, the optics don’t match the data. Aaron Boone manages scared when Montgomery’s on the mound, seemingly going batter-to-batter with the lefty regardless of pitch count in the late innings.

Would he potentially be worth more to another team than to the Yankees?

It’s also important to keep in mind that Montgomery is well aware of his worth to a team with an elite offense, elite bullpen, progressive manager, or all of the above. He hired Scott Boras to represent him in Sept. 2021, switching agencies two full years ahead of his free agency. Considering Boras rarely likes to sell his clients short on early extensions, Monty may very well be headed for free agency.

On the open market, if he continues to repeat his recent trends and eventually busts through the mid-game wall and goes deeper, the then-31-year-old could easily receive a four-year deal worth $64 million total ($16 million AAV). This offseason, a 29-year-old Eduardo Rodriguez, with worse numbers to his name, pulled in a five-year deal at $15.4 million annually.

Could the Yankees jump the gun on that and offer Montgomery four years this offseason and $65-$66 million? Would Montgomery listen?

The rest of 2022 will be a massive chance for Montgomery to make a continued statement in a rotation that’s been legendary through one month of action. He’ll be in the spotlight. He’ll receive key road and home starts. He’ll blend in a bit (as usual), but if these trends keep up, people will notice.

Now all that’s left is for the Yankees to decide how far they’re willing to go with him.

Yankees: 3 contracts on payroll holding the team back right now

The New York Yankees won't be able to splurge this offseason for a number of reasons, but these three contracts are certainly holding them back.