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Cubs free agent target: Jordan Montgomery

The Cubs need a starting pitcher. Could this be the guy?

Photo by Bob Levey/Getty Images

I had a conversation with Sara Sanchez recently in which she said the Cubs would probably sign Jordan Montgomery this offseason.

Well, why not?

Let’s have a look at what Montgomery brings to the table. After a good rookie year with the Yankees in 2017, he missed quite a bit of time the next couple of years with Tommy John surgery, then, as did a lot of players, he had a weird and freakishly bad season in 2020.

He had a good bounce-back season in New York in 2021, though oddly with only 13 decisions (6-7) in 30 starts. It was still a 3.3 bWAR season.

Somewhat inexplicably, the Yankees shipped him to St. Louis at the deadline in 2022 for Harrison Bader. That turned out to be an outstanding deal for the Cardinals. Montgomery posted a 3.11 ERA and 1.084 WHIP in 11 starts in St. Louis, including throwing a one-hit shutout against the Cubs at Wrigley Field in August. He’d also thrown seven shutout innings vs. the Cubs as a Yankee in June 2022.

The Cardinals did not do well the first half of 2023 and so Montgomery was again trade bait, sent to the Rangers, where he compiled an excellent 2.79 ERA and 1.094 WHIP in 11 starts, following that up with a 3.19 ERA in six postseason appearances (five starts) for Texas this year, including 17 strikeouts and just five walks in 31 innings.

Montgomery throws with average velocity, and relies quite a bit on offspeed stuff including a changeup and curveball:


What I like best about Montgomery is his consistency. His career ERA sits at 3.68, and that’s 3.61 since 2021. He doesn’t walk guys and has a good home run rate (1.1 per nine innings). He turns 31 in December.

MLB Trade Rumors says six years, $150 million for Montgomery, which is an AAV of $25 million. That seems about right for a pitcher of his age and ability, for his age 31-36 seasons. That’s actually somewhat less than Jon Lester got from the Cubs for the same six years of his career — his age 31-36 seasons — and of course, Lester’s deal was signed nine years ago.

Lester’s six years in Chicago produced a 3.64 ERA and 77 wins in 171 starts, not to mention multiple playoff appearances and a World Series. Jordan Montgomery isn’t quite the pitcher Jon Lester was, but I think he could match that.

If the Cubs are headed to the free-agent market for a starter, I’d be inclined to sign Montgomery for a deal like this. He’s durable and consistent and lefthanded and the Cubs could use all three of these things.


Jordan Montgomery...

This poll is closed

  • 45%
    ... the Cubs should sign him to a deal like the one proposed by MLB Trade Rumors
    (234 votes)
  • 39%
    ... the Cubs should sign him, but to a different deal in either years or dollars or both
    (207 votes)
  • 13%
    ... the Cubs should not sign him
    (69 votes)
  • 1%
    Something else (leave in comments)
    (8 votes)
518 votes total Vote Now