The Chicago Cubs have two free agent targets that are still available and they’re both willing to take shorter-term deals.
The Chicago Cubs have been one of the teams that have shown interest in both Anthony Santander and Jack Flaherty. Adding either one would greatly improve the roster on top of all the additions they’ve made already. It has been recently reported that given how cold both of their markets have been, they are now willing to accept shorter-term deals for high average annual values.
Jack Flaherty
It was first reported by MLB.com Mark Feinsand that the Chicago Cubs were one of the teams in the ‘mix’ for 29-year-old Jack Flaherty by saying:
“A number of other teams also remain in the mix for Flaherty including the Giants, Blue Jays, Tigers and Cubs.”
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 in 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.
When you look further into Flaherty’s season, he actually was better than his numbers led on, even though his overall numbers are very respectable. Looking at his Baseball Savant page he does rank in a lot of areas that show his excellence as a pitcher. Being 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.
Jack Flaherty has shown he is still a high-quality Major-League pitcher and deserves to have a deal in the five-year range and cost around $110 million in my estimation. Spotrac would appear to agree with my estimation with them having Flaherty making five million less as they figure his market value having him sign a four-year deal worth $105 million. That wouldn’t be a bad deal for the Chicago Cubs to make with them being in the market to add another starting pitcher with now being one of the teams said that they were no longer in the running for superstar free agent Roki Sasaki, adding Jack Flaherty could be a good consolation prize for the Cubs.
Anthony Santander
For the Chicago Cubs, adding Anthony Santander would be a peculiar case being they are all set in the outfield and Seiya Suzuki will be their primary designated hitter and get some time out in rightfield. However, there are some benefits that work in Anthony Santander favor.
The first of them being that Santander is a switch hitter which is a rarity in the game today and with that quality would give the Chicago Cubs lineup flexibility. Another is his availability with having played in over 150 games for the past three seasons. One more thing to highlight is when looking at Santander is his power numbers with both his slugging percentage and OPS have steadily increased with 2024 being highs for both.
The first time All-Star which he received this year, had an outstanding season for the Baltimore Orioles especially from a power perspective. Playing in 155 games Santander hit 25 doubles, 2 triples, 44 HRs, 102 RBI, for a slash line of .235/.308/.506 for an OPS and OPS+ of .814 and 134. This season marked the first time in Anthony Santander’s career that he had over 40 HRs and a hundred RBI in a season as well as a career high in runs of 91.
The Silver Slugger winner for 2024 has had a weird offseason to say the least. One would think that given the season Santander had at the plate he would’ve been one more sought-after free agents, but for most teams he is strictly a designated hitter and a liability in the outfield with having a -8 in defensive run saves.
The Chicago Cubs could figure to use Anthony Santander, but he would be blocked from having a starting spot with Seiya Suzuki still on the roster. The Cubs were rumored to be interested in trading Suzuki, but nothing has happened. If the Chicago Cubs were indeed interested in Anthony Santander, they would have to trade Seiya Suzuki who could fetch the Cubs a decent starting pitcher if Suzuki choses to wave his not trade clause.
Spotrac estimates Santander wanting to get a five-year deal worth around $89 million which comes out to about $18 million in average annual value. With Santander now indicating he’d be willing to take a shorter-term deal, but at a high AAV, the Chicago Cubs could get Santanter on a deal similar to that of Chicago Cubs current leftfielder Ian Happ.
Happ’s deal with the Cubs is three-years $61 million in which he is making $20.3 million this year and next. I think if the Cubs offered this type of deal to Anthony Santander but increased the amount to $70 million for three-years which comes out to an AAV of $23.3 million, I believe that the Chicago Cubs can get snag Santander with this deal.
Adding either would be valuable
Adding either Anthony Santander or Jack Flaherty would be valuable for the Chicago Cubs to acquire with both of them greatly improving their roster on top of the additions they’ve already made. The Cubs could look to add Jack Flaherty more than Santander being they need another starting pitcher for the rotation. Adding Santander could be valuable too with as I said the Cubs could find a suitor for Seiya Suzuki and get a starting pitcher that way as well.
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