Cubs' decision to pass on this free agent looks better than ever with latest update

For late August, left-hander Jordan Montgomery has found himself in a lot of headlines of late - and not because he's putting his team on his back for a late-season playoff push.

For starters, the 31-year-old southpaw put super-agent Scott Boras on blast this week after what Montgomery felt was a bungled trip through free agency last winter. Coming off the heels of playing a critical role in the Texas Rangers' first-ever title, projections sat in the $100+ million range for the lefty. This spring, he settled for a one-year, $25 million deal with a player option for 2025 with the Arizona Diamondbacks.

Speaking to reporters in Boston this week, Montgomery had this to say about his trip into free agency.

"I had a Zoom call with (the Red Sox), that’s really all I know. It went good. I don’t know, obviously Boras kind of butchered it, so I’m just trying to move on from the offseason and try to forget it."

Jordan Montgomery, via Boston Herald

Of course, the Red Sox weren't the only club connected to Montgomery. With Jameson Taillon expected to open the year on the IL as early as March, the Cubs made a ton of sense and near-daily speculation connected Jed Hoyer's club to the veteran. The two sides never really seemed to get close to getting a deal done and Chicago entered the year with a rotation of Justin Steele, Shota Imanaga, Jordan Wicks, Javier Assad and Kyle Hendricks.

Cubs' starting rotation has been the anchor Jed Hoyer hoped for

The rotation, even with an Opening Night injury that cost Steele more than a month on the shelf, has been a major strength for the Cubs all season long. Meanwhile, things have gone from bad to worse for Montgomery in Phoenix, where the Diamondbacks have moved him to the bullpen due to ineffectiveness as a starter.

The USC product entered Saturday with a 6.44 ERA across 19 starts this season, with a walk rate that's up and a strikeout rate that's down. He's allowed nearly a dozen hits per nine innings and there's no doubt his standing has fallen dramatically across the league. Given all the talk about avoiding dead money on the books heading into 2025, it's safe to say that passing on Montgomery is a win for Hoyer and the Chicago front office at this point.

Imanaga is a likely Rookie of the Year finalist in the National League. Steele has bounced back from his early season injury to be the same dominant presence he was in 2023. Once healthy, Taillon has been a steady, reliable arm behind them and Assad has exceeded most expectations, despite a late-season fade due to the heaviest workload of his career.

Hendricks, a prime DFA candidate earlier in the year, has settled in and been a 4.00 ERA-type pitcher for the last two or so months, helping offset the loss of Wicks, Hayden Wesneski and young right-hander Ben Brown, all of whom have spent significant time on the IL.

The Cubs' reported unwillingness to give Montgomery a long-term deal last winter, which, at least in part, was probably driven by a renewed belief in the organizational pitching infrastructure, seems to have paid off. Instead of $20 million tied up in a guy worth -1.5 bWAR this year heading into 2025, the team has maintained a high level of financial flexibility - which should translate into meaningful additions this offseason.