Why is Jordan Montgomery Still Unsigned?

With the MLB season rapidly approaching with opening day for 28 teams being less than a week away, one key player still remains a free agent - LHP Jordan Montgomery. Montgomery (31), entered this offseason as one of the prized pitchers, but he, alongside fellow Scott Boras client Blake Snell, remained unsigned until 6 days ago, when Snell inked a 2 year 62 million dollar deal with the San Francisco Giants. While Snell has signed, the 2023 Postseason hero Montgomery remains a free agent, with very little rumors surrounding him. So, it begs the question - why is Jordan Montgomery still unsigned?

Insistence on a Long-Term Deal

The biggest reason for why Montgomery has gone unsigned is his insistence on receiving a long-term deal in the realm of 20-25 million dollars per year. While this is a hefty amount, Montgomery deserves it with the way he has pitched over the last 2 seasons, posting a 3.34 ERA and 1.144 WHIP in 367 innings. Furthermore, Montgomery, along with Nathan Eovaldi, spearheaded the Rangers’ rotation in their quest for their first World Series last season, as he had a 2.90 ERA and 1.35 WHIP in 31 postseason innings, going 3-1 in his 6 appearances. 

While Montgomery's performance has been phenomenal over the last two years, 2022 and 2023 were the only seasons in his career where he made over 21 starts in a single season since his rookie year in 2017. This leads me to the second reason for why Montgomery has not been signed yet.

The Risk Factor

Montgomery has only pitched over 150 IP 3 times in his career, and has also already undergone Tommy John surgery back in 2018. Given that he will be 31 this upcoming season, there is concern if he can stay healthy enough to be productive over a long contract. Furthermore, teams are afraid to pay Montgomery because had his best season last year after the trade deadline with the Rangers, as he posted a 2.79 ERA and 1.094 WHIP in 11 starts - significantly better stats than his career averages (3.68 ERA, 1.209 WHIP). Though Montgomery has shown an upward trajectory in his career, teams are afraid of giving him ace-level money for fear that he peaked last season and in the postseason. 

TV Deal Dilemma

Almost 20% of the revenue teams earn comes from their TV Deal with their regional network. However, with Diamond Sports Group (Bally Sports) nearing the end of its bankruptcy restructuring phase, many teams are left to wonder who their regional network will be for this upcoming season and on. With this expected sharp decrease in revenue, owners are unwilling to open their checkbooks and give players hefty contracts, leaving players like Montgomery stuck in free agency. 

Montgomery’s market is unlikely to change any time soon, as teams are still only willing to give him a short-term contract. Like Cody Bellinger, Blake Snell, and Matt Chapman, it may be in Montgomery’s best interest to take a one or two year deal and re-enter free agency after the contract is done.