Jordan Montgomery, Jon Lester, and Some New Rumors with the Chicago Cubs

Jordan Montgomery

It’s January 5. I don’t think I need to do a lengthy preamble, right? By now, we all know the score: The Cubs theoretically have money to spend this offseason, they need at LEAST one starting pitcher, preferably someone who can slot into/near the front of the rotation, and Jordan Montgomery is one such available free agent. Bing, bang, boom.

But is he a realistic option for the Cubs? Well … actually maybe? And there are actually a couple of fresh rumors to share to that end.

Jordan Montgomery: Twice Connected to Cubs

Before today, the last time the Cubs were connected to Jordan Montgomery was all the way back on December 1, when Jeff Passan labeled him as a potential “strike-first option” for Chicago. Heh. No strike was made, and it took a month for them to even be reconnected.

Earlier today, Jim Bowden said that the Cubs “remain in the mix for Cody Bellinger, Rhys Hoskins, and Jordan Montgomery….”, which is interesting.

Everyone knows the Cubs are connected to Hoskins and Bellinger. Those rumors have been plentiful, persistent, and recent. Montgomery, by contrast, is not a name we’d heard in a while.

Of course, Bowden finished that thought by reporting that the Cubs “haven’t been aggressive enough to get close to signing any of them, according to major-league sources.” (Which … lol, this offseason stinks.) But still. The mention is notable, particularly in tandem with a second.

Bowden wasn’t alone. Patrick Mooney also randomly mentioned Jordan Montgomery as a fit for the Cubs today, albeit in a less-sexy way: “Among the top free agents represented by Boras, Jordan Montgomery is viewed as a better potential fit for the Cubs than Blake Snell, per a team source….”

And, of course, he had a similar, disheartening follow-up quote: “though it’s unclear how far Hoyer’s group is willing to go in that pursuit of pitching.”

So, you’ve got Montgomery twice being connected in the same day to the Cubs, but also some serious hedging language. You might call a signing plausible, but unlikely.

Jordan Montgomery: Price Tag and Comps

We discussed Jordan Montgomery, the pitcher, in great detail back when that Passan rumor first came out. So head over to this post for all that information/convo on his track-record, recent playoff performance, and sinker.

One thing I want to pull out of that convo to discuss today, though, is the projected price tag and one notable comp:

“Executives that spoke to Jeff Passan estimate a deal in the six-year, $140M range, though the panel at The Athletic was much lower (5/$105M). And they have him as the sixth best free agent this offseason for whatever that’s worth. It’s tempting to want to compare these figures to the deals given to Jon Lester (6/$155M) and Yu Darvish (6/$126M), but those deals are WAY out of date. The price of poker has gone up significantly, and I think you’d be wise to adjust your expectations accordingly.”

In addition to those predictions, MLB Trade Rumors projected a deal in the range of six-years, $150M. But like I said in that quote above, you just can’t compare the deal for Lester (2015) and Darvish (2018) to what Montgomery might get today. Lester’s deal was a LONG time ago, and prices have gone up.

Since Lester signed his deal, Yoshinobo Yamamoto ($325M), Gerrit Cole ($324M), Stephen Strasburg ($245M), David Price ($217M), Zack Greinke ($206.5M), Jacob deGrom ($185M), Aaron Nola ($172M), Carlos Rodon ($162M) all signed larger guarantees (that was just off the top of my head, too, not sure if I’m missing someone). And that’s not including the high AAVs for other free agents like Max Scherzer ($43.3M), Justin Verlander ($43.3M), or Trevor Bauer ($34M).

Point being, $150M or so is nowhere near the top of the market anymore. So get Lester out of your head in terms of financials and expectations. If Lester was expected to be an ace based on ~$150M, Montgomery would not have the same expectations if at the same price point. That is just the cost of a very good, non-ace starting pitcher in today’s game.

Unsurprising, then, to hear that Montgomery may actually be seeking a deal that tops the seven-year, $172 million contract the Phillies just gave Aaron Nola.

Jordan Montgomery
(Photo by Getty Images)

But, is Jordan Montgomery Kinda Jon Lester?

So, like I said, even if you didn’t expect Montgomery to be Lester in performance, you might expect him to get a contract pretty similar to the one Lester got nearly a decade ago, if not better.

Except also there is this weird and shockingly close comparison going around Twitter that really makes you think. You might have to click in to see the full image, but the long and short of it is for the three years preceding their free agent season, Jon Lester and Jordan Montgomery have eerily similar numbers.

Not only that, both Lester and Montgomery were/are entering their age-31 season for free agency. They were also both traded mid-season before free agency (no Qualifying Offer), and had great numbers in the playoffs before hitting the market. They’re also both lefties in case you just glossed over that.

That’s not all to say that Montgomery will age as well as Jon Lester did. You’d have to dig into the actual underlying metrics and pitch quality, not just the top-level results and more surface similarities, but $150M just isn’t out of whack with what he’s done in the past. It arguably wouldn’t have been 10 years ago, I guess, but it certainly isn’t now. And it doesn’t hurt that Jordan Montgomery is not attached to draft pick compensation, which we know some teams value in the $10-$20M range.

All of that is to say, I absolutely hope the Cubs will be involved on Montgomery, and I think a deal in that $150M is plainly fair if he cannot get a deal that goes even higher. If his price tag DOES go higher, it still might be worth staying involved.

written by

Michael Cerami began covering the Chicago Cubs for Bleacher Nation as a part-time contributor in 2015. One year later, he joined Bleacher Nation full-time, covering the Chicago Cubs and Major League Baseball. Today, Michael runs Bleacher Nation, contributing as a writer (Cubs, MLB) and an editor for all sections of the site, including the Chicago Bears, Bulls, and Blackhawks, as well as MLB, NBA, NHL, and NFL. In 2019, Michael was the co-host of NBC Sports Chicago's Cubs Post-Game Show Outside the Ivy. You can find him on Twitter/X @Michael_Cerami

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