The Chicago Cubs have done well and have been relatively active this offseason. They have made many of their big moves through the trade market, leaving the free agency market to be used to add to ‘the margins‘ as Jed Hoyer said they would do.
The Cubs were heavily in on top free agent reliever Tanner Scott until the reigning World Series Champions the Los Angeles Dodgers swooped in at the last minute and gave Scott just a little more money to sign with them.
Now that Scott is gone, the Cubs have to pivot and shift their focus to other names on the market to add to either their starting rotation or the backend of the bullpen. Names like Carlos Estevez, Jack Flaherty, and Danny Coulombe are still available, and the Cubs are bound to land one of them.
It hurts to lose out on the top free agents
The Cubs were heavily invested in both superstar pitcher Roki Sasaki to bolster their starting rotation and Scott to bolster the bullpen and pair with Porter Hodge in the backend. Both would’ve been great additions for the Cubs to have on their roster which is taking form into becoming a possible playoff-caliber team. The Dodgers have been seemingly stealing all the Cub’s targets this season by not just scooping up Sasaki and Scott but also signing the versatile Korean superstar Hyeseong Kim as well. Now that all these valuable players are off the board for the Cubs, they will need to shift their focus to other free-agent targets still on the board.
General Manager of the Cubs Carter Hawkins spoke of the process of trying to sign Sasaki per MLB.com:
“It was a fair process,” Cubs general manager Carter Hawkins said on Saturday at the Sheraton Grand Chicago. “We had a clean shot to say what we wanted to say to Roki and his representation. A lot of teams did. I think he heard everything that we wanted to say.
“I’d reiterate – I don’t know how much we’ve talked about this publicly – but the entire organization did such an unbelievable job in just putting our best foot forward. It stinks not to get him.”
Options still available for the Chicago Cubs
President of Baseball Operations Jed Hoyer recently joined the David Kaplan’s “The REKAP” #Takethat YouTube Channel podcast where he was asked about what the rest of the Cubs offseason plans will be. When asked Hoyer answered with stating the plan will be:
“Mostly focused right now on bench and bullpen, just trying to supplement the roster as much as we can. I feel good about our team but there’s obviously ways to improve,” Hoyer said. He later added that the “bullpen’s been probably the area we’ve been focused on most in free agency. I feel like we’re trying to make sure we upgrade our bench. Adding a veteran presence to our bench would be good.”
This is great with the Cubs needing to possibly add another platoon partner for top prospect Matt Shaw at third base as an insurance policy in case he shows signs of struggling. However, the starting rotation needs an upgrade as well the Cubs still should look to add one more piece there.
The best option still available on the free agent market for starting pitchers is 29-year-old Jack Flaherty. The Chicago Cubs are very familiar with the 29-year-old Flaherty who pitched for their divisional rival the St. Louis Cardinals for seven years (2017-2022). Jack Flaherty had a solid 2024 season which started with him signing a one-year deal with the Detroit Tigers who at last year’s trade deadline shipped him over to the Los Angeles Dodgers where he ended his season winning the 2024 World Series.
Overall, in 2024 between both the Detroit Tigers and Los Angeles Dodgers Flaherty made 28 starts posting a record of 13-7 with a very respectable 3.17 ERA, having just six strikeouts shy of a 200-strikeout season (194), a WHIP of 1.068, in a total of 162.0 innings of work. Further looking into Flaherty’s season, he was better than his numbers led on, even though his overall numbers are very respectable.
Looking at Flaherty’s Baseball Savant page he does rank in a lot of areas that show his excellence as a pitcher. He was in the 98th percentile for his breaking run value (12), as well as being in both the 90th and 91st percentile for whiff percentage (32.1%), and K percentage (29.9%), which is why Flaherty also had a strikeout per nine rate of 10.8 in 2024 and shows he is still able to miss bats.
It was recently reported that Flaherty and his camp would be willing to sign a shorter-term deal, but it must have a high average annual value. With the way things are going on the market, the Cubs might have to consider ‘overpaying‘ to get Flaherty or another free agent to come to the northside.
Possibly overpaying for a free agent to come to the Northside
I know that owner and chairman Tom Ricketts may not want to hear that with his recent comments being:
“They think somehow we have all these dollars that the Dodgers have, or the Mets have or the Yankees have, and we just keep it. Which isn’t true at all. What happens is we try to break even every year, and that’s about it.”
Sometimes, however, if you want to have a winning roster and team, you have to spend a decent amount of money to do that. The formula to winning is a mixture of having young controllable players, mixed in with veterans, and sprinkling in a few high-priced free agents to all come together and form a roster. These comments by Ricketts now make sense and are honestly pretty relieving on how the Cubs have been operating for the past few seasons. The Cubs are a big market team with the third largest television market in the country but operate like they’re the Athletics or the Colorado Rockies, which is unacceptable.
The same thing will hold if the Cubs are interested in landing Carlos Estevez. The Cubs have competition in possibly the Toronto Blue Jays and Red Sox being in the running but given the recent track record that could bode well for the Cubs. Hopefully, a deal can get done soon for either Flaherty or Estevez before another team snags either of them away.
The Chicago Cubs sign a decent reliever to a minor league deal
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