Yankees, Jordan Montgomery have reopened discussions

The Yankees are “back in contact” with Jordan Montgomery’s camp at the Boras Corporation, reports Jon Heyman of the New York Post. Heyman adds that there’s still a gap between the southpaw’s asking price and the team’s comfort level.

Montgomery is the highest-profile player available in free agency. He’s not the last notable Boras Corp. client who remains unsigned — J.D. Martinez has also lingered on the market — but he is the final member of the top group that included Cody Bellinger, Matt Chapman and Blake Snell. All of those players eventually moved to short-term guarantees (three years for the position players, two for Snell) that allow them to opt out next offseason.

The 31-year-old Montgomery has reportedly been less amenable to that kind of arrangement. Heyman wrote that Montgomery was looking for a seven-year pact as recently as March 8. Early in the winter, his camp had tried to beat the $172M guarantee that Aaron Nola landed to return to Philadelphia. Neither mark seems especially plausible just a week before Opening Day.

Part of Montgomery’s aversion to a short-term pact could be the qualifying offer. Since he was traded from the Cardinals to the Rangers midway through the 2023 season, he was ineligible to receive the QO. He hit this year’s market unencumbered by draft compensation. Each of Snell, Bellinger and Chapman declined a QO. They’re all ineligible to receive the offer again, as the collective bargaining agreement prevents a player from being tagged more than once in his career.

Montgomery could still receive the QO in a future winter, which could make the possibility of retesting free agency in a year comparatively less appealing. As MLBTR’s Darragh McDonald explored this afternoon, one option would be to wait until after the start of the regular season to sign. Only players who are on the same team for the entire preceding season can receive a qualifying offer.

It’s not clear how much that’s a calculus in Montgomery’s decision. Perhaps he was simply the most patient of the group in hoping that a long-term pact would present itself. That was clearly what he envisioned when he hit the open market after helping Texas to the first World Series in franchise history. Montgomery is coming off a personal-low 3.20 ERA in the regular season. He has reached 30 starts while allowing fewer than four earned runs per nine in each of the last three years.

For many players, the market simply hasn’t materialized the way they’d anticipated. The Rangers have cited concern about their local broadcasting contract as a reason for a relatively quiet offseason. Texas took a reduced rights fee to keep their contract with Diamond Sports Group for another season. While their deal had previously paid a reported $111M annually, Heyman reported yesterday that they’ll receive $90M for this year. There’s still broad skepticism about Diamond’s viability beyond the upcoming season.

The Yankees have no such concern about their television contract, as they’re very well positioned as co-owners of the YES Network. Their major spending deterrent is the luxury tax. New York is beyond the $297M figure that marks the fourth tier of penalization. They’ve paid the CBT for two consecutive seasons, subjecting them to the highest penalties. The Yankees would owe a 110% tax on the average annual value of any additional signing.

That has evidently kept them from addressing a rotation that looks tenuous. Gerrit Cole will be out into May or June after experiencing elbow inflammation. New York parted with Michael King, Jhony Brito, Randy Vásquez and Drew Thorpe in the Juan Soto trade. Their only significant rotation acquisition this offseason has been a two-year deal for Marcus Stroman.

New York announced that Nestor Cortes will take the ball on Opening Day. He’ll be followed in the rotation by Carlos Rodón, Stroman and Clarke Schmidt. The fifth spot could fall to swingman Luke Weaver or a young pitcher like Clayton Beeter, Luis Gil or Will Warren. That’s already a risky group and there’s not much proven depth if anyone else from the top four suffers an injury.

Montgomery probably wouldn’t step into the Opening Day rotation given his lack of competitive Spring Training work, but he has been incredibly durable since undergoing Tommy John surgery in 2018. There’s a clear on-paper fit for a return to the Bronx. While Montgomery had some parting shots for the front office after being traded to St. Louis at the ’22 deadline, Stroman had also publicly criticized the Yankees before signing his deal. Montgomery has been loosely linked to the Red Sox and Mets in recent weeks, yet neither franchise seems keen on making a significant investment at this point of the offseason.