Cubs Remain in the Mix for Top Free Agent Starter

We're all waiting for the Roki Sasaki decision to drop and once it does we should see the rest of the free agent pitching market pick back up. Team insiders remain confident that the Cubs will add another starting pitcher and interestingly enough the Cubs are supposedly still in the mix for the top free agent starter in free agency.

The Cubs have been linked to right-handed starter Jack Flaherty since last summer in trade rumors and they've been loosely connected in free agent rumors this offseason as well. The 29-year-old is the top starting pitcher left after the surprising deal struck between the Arizona Diamondbacks and Corbin Burnes.

While the Cubs have explored trade options this winter to upgrade their starting rotation, MLB.com's Mark Feinsand recently said they're still hanging around the Flaherty sweepstakes.

Via MLB.com.

With few alternatives in free agency, the Orioles could turn to the trade market -- San Diego’s Dylan Cease and Seattle’s Luis Castillo are among potential trade candidates -- to fill the hole atop the rotation, but a reunion with Flaherty would make perfect sense.

A number of other teams also remain in the mix for Flaherty including the Giants, Blue Jays, Tigers and Cubs.

Maybe this is reading too much into the wording, but "remain in the mix," gives off the impression that the Cubs have had some sort of contact with Flaherty this offseason.

Seeing that Flaherty has not signed yet it's easy to assume that no team has exactly stepped up with an overwhelming offer to win over the free agent righty.

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. Or do the Cubs stretch out the contract to lower the AAV?

While the Cubs and several other suitors of Sasaki are waiting, so is Flaherty, who will become the main focus on the starter market in a couple weeks.