Dodgers Free Agent Could Make Sense for Cubs Offseason Plan

The Chicago Cubs are not going to be pursuing any of the top free agent starting pitchers this offseason and while that remains frustrating it doesn’t mean the team can’t sign a quality arm. Blake Snell just agreed to a five-year, $182 million deal with the Los Angeles Dodgers, which I think means Jack Flaherty is no longer in their plans. However, the 29-year-old could make sense for the Cubs, who we do know will be focusing on that upper, middle-tier of free agent pitchers this offseason.

Before the Snell signing, MLB insider Mark Feinsand wrote about free-agent fits for every team and when it came to the Cubs he matched them up with Flaherty. Again, it looks like the righty has lost a suitor with the Dodgers making an early move for Snell. So, that’s one big shark out of the water for Flaherty if the Cubs do indeed pursue him.

Via MLB.com.

Chicago will look to upgrade its rotation this winter, and while top free agents such as Corbin Burnes and Max Fried aren’t completely out of the question, the likelihood is that the Cubs will be focused on the second tier of starters. Flaherty made the most of his one-year, $14 million deal in 2024, pitching well for the Tigers before helping the Dodgers win the World Series following a midseason trade.

Lots of things to like about Flaherty. For starters, he’s one of the younger pitching arms available in free agency this offseason, turning 29-years-old back in October. Then you go to his recent results and you love what you see even more.

In 2024, Flaherty recorded a 3.17 ERA and 1.07 WHIP between his time with the Detroit Tigers and Dodgers. The righty struck out 194 batters in 162 innings, matching a career high strikeout rate of 29.9%. He held opposing hitters to a .222 batting average and Flaherty’s peripherals were also good, keeping hard contact in check.

The main concern? Flaherty does have a track record of injuries popping up. In 2021, Flaherty had a 3.22 ERA for the St. Louis Cardinals, but was limited to 17 total appearances and 15 starts. The pitcher’s year was interrupted because of an oblique strain that occurred while batting. Remember when pitchers still hit? That was Flaherty’s first IL stint and after coming back later in the season he was back on injured list, but this time he had a shoulder issue.

That right shoulder became a problem again in 2022 and Flaherty only pitched in nine games for the Cardinals that season, missing three full months in the middle of the year. He ended the year with a 4.25 ERA in 36 innings.

So, after a good beginning to his career, Flaherty hit a speed bump in 2022 and his 2023 season only got worse, posting a 4.99 ERA in 144.1 innings with the Cardinals and Baltimore Orioles. So, what do you believe in, will Flaherty revert to that tough stretch or will he settle in as the overall solid pitcher he’s been when fully healthy?

Overall in his career, Flaherty has pitched to a 3.63 ERA in 829.2 innings, making at least 27 starts in four of his six full MLB seasons.

Now that Flaherty is a full year removed those 2023 struggles and showed that he can be a dependable starter again, actually a really good starter again, I lean toward buying on the 29-year-old this offseason. Will the Cubs feel comfortable going to his price is obviously the big question.

Here are some contract projections for Flaherty.

MLBTR: 5 years, $115 million
Fangraphs: 4 years, $88 million
ESPN: 5 years, $115 million
The Athletic: 4 years, $92 million

The Cubs haven’t gone to the top of the free agent market under Jed Hoyer and while the team hasn’t gone beyond four guaranteed years for a starting pitcher, I could see them going to these lengths if they’re all in on Flaherty.

Marcus Stroman was signed to a three-year deal that could have been worth $71 million in its entirety. Stroman opted out after the second year. Jameson Taillon signed a four-year, $68 million contract and Shōta Imanaga’s four-year, $53 million deal could end up being worth $80 million over five years.

I would say that the chances of the Cubs signing Flaherty become higher if the contract does stay below that $100 million mark and you know the front office prefers shorter deals, so four years is probably what Hoyer and company would shoot for. We’ll see how Flaherty’s market plays out this offseason.

Another Dodgers free agent has also been linked to the Cubs and maybe he’ll be the one to fall into the team’s range. Read more about Walker Buehler here.