3 free agent starting pitchers the Cubs could still realistically add this winter

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You'd never know it scrolling X, but there's still a good chunk of offseason left - and a number of quality free agents still on the board. Many of those free agents are potential fits for a Chicago Cubs team that has holes in the outfield, at both corner infield spots and in the pitching staff.

Looking specifically at the starting rotation, headlined by Justin Steele, Chicago could do itself a favor by adding another top-shelf arm to put alongside their young left-hander, who dominated his way to a fifth-place finish in NL Cy Young voting in 2023.

Funnily enough, the three guys I'm about to take a closer look at are all also left-handers, which could have a nice trickle-down effect on a Cubs bullpen that badly needs someone like Drew Smyly in the mix, as opposed to working out of the rotation.

3 big name free agent starting pitchers the Cubs could still add: #3 - Blake Snell

Hey, think big, right? It's been essentially silent on Blake Snell all winter, which makes sense because his market will really take shape after the offseason's top pitching prize, Yoshinobu Yamamoto, signs - which could happen soon.

Snell, now a two-time Cy Young winner, was marvelous for San Diego last year, putting together a run from June on that was reminiscient of former Cubs ace Jake Arrieta during his 2015 Cy Young season. In the second half, the left-hander posted a 1.54 ERA in 14 starts, and he also carried sub-1.00 ERA in three separate months: June (0.87), July (0.56) and September (0.58).

The Cubs need somebody to pair with Steele atop the rotation and, while Snell doesn't come without his own red flags (he led the league in ERA, but also led MLB in walks last season), he would also represent a major upgrade at the top of the rotation.

3 big name free agent starting pitchers the Cubs could still add: #2 - Jordan Montgomery

You're going to pick up on a theme here. Jordan Montgomery, like Blake Snell, will see his market at least somewhat dictated by the Yamamoto sweepstakes. He did right by himself in the postseason with the Texas Rangers, working to a 2.90 ERA in five October starts en route to earning his first World Series ring.

A reunion with Texas still seems like a possibility, especially given the recent update on Max Scherzer's status, and the Yankees have also talked about bringing him back - but that might be contingent on them missing out on Yamamoto.

By and large, Montgomery has been the epitome of consistency in his career, especially since the start of the 2021 campaign. His stepping up in the postseason helped boost his resume, for sure, but he'll still probably net a deal well south of what Snell will get given their respective track records. That fact alone might make him more likely to land in Chicago.

3 big name free agent starting pitchers the Cubs could still add: #1 - Shota Imanaga

While it's been all eyes on Yamamoto of late, another Japanese starter, Shota Imanaga, is also poised to make the jump to the big leagues this winter - and the Cubs have been a speculative fit for some time now.

The left-hander, expected to net a four or five-year deal, averaged north of 10 K/9 last season - leading all NPB hurlers with 174 punchouts. He's not an overpowering presence, but is widely regarded as one of the top pitchers in Japan, with a low-to-mid 90s fastball, mixed with a nasty splitter, a curveball and a slider.

A control artist, Imanaga doesn't issue many free passes and if he can work down in the zone, he could take advantage of the Cubs defense behind him. Again, he's not going to get a deal anywhere close to what Yamamoto will fetch, nor will he likely be as dominant - but he's got a track record of success that make him a nice fit on this team as its competitive window opens.

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