With less than a week remaining until Opening Day, left-hander Jordan Montgomery stands alone as the clear top free agent remaining on the market. That could change in the coming days, however, as Jim Bowden reported on MLB Network Radio this morning that the southpaw’s camp has two “long-term” offers on the table and that he could sign somewhere as soon as this week. It’s unclear which teams have made an offer to Montgomery at this point, though he’s be connected to the Yankees and Red Sox in recent weeks.
One club it appears is not among the two teams to have made an offer to Montgomery at this point is Philadelphia, though that’s not to say the Phillies don’t have interest in the lefty. According to USA Today’s Bob Nightengale, the Phillies are “internally discussing” a pursuit of Montgomery, though he adds that a decision on whether or not to contact Montgomery’s agent, Scott Boras, about a potential deal has not yet been made. Meanwhile, MLB.com’s Todd Zolecki reported recently that the Phillies had previously shown interest in Montgomery on a one-year deal prior to the start of Spring Training last month, though he adds that the club’s interest has “cooled” in the weeks since camp began.
All of that would seem to indicate that Philadelphia is something of an unlikely landing spot for Montgomery, unless the club not only reopens negotiations with the 31-year-old’s camp but also expands their interest beyond a one-year deal into a potential multi-year arrangement. Signing a multi-year pact could certainly make some sense for Montgomery, as the southpaw was ineligible to receive a Qualifying Offer this winter and therefore is likely to see his stock negatively impacted by one in a second trip through free agency.
Of course, as recently discussed by MLBTR’s Darragh McDonald, Montgomery wouldn’t be eligible for a Qualifying Offer this coming winter if he were to sign with a club after Opening Day. Speculatively speaking, that could create a situation where Montgomery remains focused on finding a multi-year deal in the days leading up to Opening Day without considering one-year arrangements until it, and his eligibility for a Qualifying Offer this coming winter, have already passed. Reporting earlier this month suggested that Montgomery was hoping to land a seven-year deal, though it’s unclear if either of the reported offers Montgomery currently has in hand approach that length.
With that being said, a lengthy deal that features a deflated average annual value could make a great deal of sense for a club such as the Yankees that has is approaching or has already surpassed the highest threshold of the luxury tax. Any expenditures over the final $297MM threshold are taxed at a 110% rate. That reality left the Yankees reportedly disinterested in engaging with Montgomery’s fellow top-of-the-market southpaw, Blake Snell, as he pivoted towards prioritizing a short-term deal at a high AAV.
The two-year, $62MM deal Snell signed with the Giants earlier this month came with an AAV just under $30MM, which would have left the Yankees to pay more than $32MM in taxes on top of the lefty’s actual salary had they signed him to that same deal. Speculatively speaking, it’s possible that both sides could benefit as the lefty could get the long-term security he’s reportedly searching for while New York would enjoy a much smaller tax bill on a yearly basis if Montgomery were amenable to a lengthy deal at a much lower annual salary.
Of course, given how close we are to the start of the regular season, it’s fair to wonder just how quickly Montgomery would be ready to enter a club’s rotation even if he were to sign before Opening Day. It’s possible he wouldn’t be too far behind, as Travis Sawchik of theScore reported this morning that Montgomery has ramped up to 75 pitches in preparation for the start of the season. On the other hand, Sawchik acknowledges that Montgomery’s preparation process may not be a perfect analogy for work in Spring Training, which involves facing live, big-league caliber hitting and working with a club’s coaching staff. Given those discrepancies, it would be somewhat surprising if Montgomery were able to start for a club on Opening Day at this point, though it’s at least reasonable to think that his ramp-up process will shorten the time he needs to prepare for the season once signed.