The calendar has officially turned to 2024 and Jordan Montgomery remains a free agent. He is one of the best starting pitchers still available. It is Blake Snell, Shota Imanaga, Montgomery, and then maybe Marcus Stroman among free agents. The market is picking up, but Boras clients Snell and Montgomery remain unsigned. There is smoke out there indicating that a reunion with Montgomery might be in the works. Two questions need to be asked regarding this potential signing. First, what is holding up the signing if Texas has interest and Montgomery has interest in returning? Second, is Texas willing to give Montgomery a six or seven-year contract? Let us answer both of these questions and try to piece together whether this is something that will actually happen.
What is holding up Texas signing Jordan Montgomery?
There are probably two factors in play that are currently keeping Montgomery from signing back with Texas. First, is that Scott Boras is his agent. It is not a negative against Boras, but he does try to get every last dime he can get for his clients. That sometimes will include keeping free agents on the market into late January or early February. An example of this was Bryce Harper's signing with Philadelphia back in 2019 after pitchers and catchers had reported. He has proven that he will wait it out to get the most money for his clients. I do not think there is any rush to get this done especially with still 40 days until pitchers and catchers are supposed to report.
The second factor is the media rights deal with Bally Sports. I do think Texas is waiting to find out how much money they will get paid this season for their television rights. Jon Heyman reported in the New York Post on Thursday that there has been movement on that front. Heyman says, "there maybe a one-time payment of $90 million." If that is true then that would allow Texas to be able to sign Montgomery.
It does seem like the consensus around baseball is that Montgomery wants to return to Texas. Jon Heyman earlier this week said this in his livestream,
That was followed up by Randy Miller of NJ.com. He is a Yankees beat writer and in his latest column he said this about the Yankees and Jordan Montgomery,
"The person told NJ Advance Media of a growing belief within the organization that left-hander Jordan Montgomery is headed back to the Rangers — and not returning to the Yankees."- Randy Miller
I don't think that was the case last month, but this free agency does seem to be turning in Texas' favor. Montgomery might be waiting to see what Texas will offer once the Bally Sports situation is settled. In this case, time is on the side of the Texas Rangers. Montgomery can continue to wait and if the offer is not there then he can circle back with the Yankees, Red Sox, Phillies or some other team and still sign in plenty of time for Spring Training.