Where Can Cubs Turn After Missing Out on Tyler Glasnow?

The Tampa Bay Rays and Los Angeles Dodgers agreed to a deal Thursday to send Tyler Glasnow to Los Angeles, along with outfielder Manuel Margot. The Rays will get young, controllable starting pitcher Ryan Pepiot and outfield prospect Jonny DeLuca in return. As of early Friday morning, though, the deal isn't official, because it's contingent on Glasnow and the Dodgers agreeing on a contract extension to keep him around beyond his scheduled free agency at the end of 2024.

For a long time this offseason, fans grew more anxious, but little actually changed. Although the Cubs haven't addressed their fairly dire need for help at the front end of their rotation, they also hadn't missed out on many of their realistic options to make that upgrade. Now, though, the music seems to have stopped, and chairs are filling up. The team needs to find one soon, and Glasnow marks a very oft-mentioned target taken off the board. While his lack of durability is an important mark against Glasnow, the other argument not to acquire him was that he'd only be around for one year. That the Dodgers are getting him to sign an extension to make this deal work makes this feel like more of a miss for the Cubs.

Soon, another important miss will also become official. Yoshinobu Yamamoto's lucrative free-agent sweepstakes continues, but the Cubs seem not to be a serious player in it. One by one, the pitchers who could materially change the look and feel of the Chicago rotation are finding their new homes, and none (so far) are on the North Side of Chicago.

Three good options do stand out, though. It's not too late to flip the script. Let's break down the situation with each hurler.

Shota Imanaga
Of the remaining pitching targets, the most intriguing is Imanaga. It's pretty clear, by now, that his market will reach the $20-million annual average value range, and it's likely to be a five-year deal. That's a big payout to a 30-year-old, but as I've written before, Imanaga has a ton of upside. If the Cubs can land him, they'll have the swing-and-miss element that has been missing from their rotation the last several years. Imanaga's strikeout-to-walk ratio of 188:24 in NPB this year is like something out of a video game, especially given that he did it while facing only 637 batters.

Against MLB hitters, he'll need to make some adjustments, and both of those rates are likely to move in the less desirable direction. They have plenty of room to do so without posing a problem, though. Imanaga's sheer stuff supports the numbers and suggests he could keep them up, to some extent. As we've discussed recently, it doesn't seem like the Cubs are willing to go far enough to sign top-end superstars in free agency, but Imanaga fits into the range to which they do seem willing to stretch.

Shane Bieber
The Cubs and Guardians have had substantial trade talks around a number of names and involving a lot of potential combinations of young Cubs talent, but one player who stays right in the center of the conversation is Bieber. He's not a Glasnow-like swing-and-miss maven, at this point in his career, but he does several things well and has a deep repertoire. He's the kind of starting pitcher the Cubs have tended to value more highly than most of the rest of the league.

With the precedent set anew by the Glasnow deal, it wouldn't be shocking to see the Cubs try to secure an extension with Bieber before completing a trade. In 2024, the hope is that he would be a No. 2 starter, but for the handful of years after that, he would project as more of a mid-rotation option. An extension that ensured he would be a long-term replacement for Kyle Hendricks (who needs to slide to the back of the rotation mix in 2024 and is likely to leave thereafter) would make a trade for Bieber more exciting.

Jordan Montgomery
If any free agent smoothly blends the reliability and control of Bieber with the upside of Imanaga, it's probably Montgomery. I discussed why he's a good fit for the Cubs, from a pitching philosophy perspective, earlier this offseason. The market for Montgomery is yet to gain full heat, but that figures to change as Glasnow and Yamamoto come off the board, and it could move quickly at that point.

He doesn't miss bats the way you'd like your front-end starter to do so. That's the knock on Montgomery. His durability is superb, though, and he fills up the strike zone. He also does things with seam-shifted wake and the unique release point on his high, over-the-top deliver that make him tough to read and tough to hit. It's unlikely that the Cubs can afford both Imanaga and Montgomery, and if they do want to sign Montgomery, they might prefer not to extend Bieber, so as not to overcommit to mid-rotation hurlers for the long term. Still, it might be that the Rangers' co-ace for the stretch run is the right guy to prioritize.

Which of these three hurlers strike you as most likely (or most desirable) for the Cubs? Who else is still on your radar? Let's talk about raising the ceiling in the rotation, even if it can't be with Glasnow or Yamamoto.