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The big-market Chicago Cubs are sitting at home while the Milwaukee Brewers, their small-market rivals 90 miles north up I-94, play in the World Series.
That must be particularly frustrating for Cubs fans, who have watched the Brewers now win four consecutive National League Central titles despite substantially smaller payrolls. Chicago even hired manager Craig Counsell from the Brewers to a five-year, $40-million contract three years ago and still hasn’t been able to catch Milwaukee.
The Cubs finished this year with an 89-73 record and reached the postseason. However, they were a whopping 14 games behind the Brewers, then got outscored 12-1 in a two-game sweep by the San Diego Padres in an NL Wild Card Series.
President Jed Hoyer and general manager Carter Hawkins have a chance to significantly reshape the roster in the offseason, as the Cubs have as many as 18 players who could become free agents depending on whether contract options are exercised. The team could also shed as much as $100 million from its payroll.
Of course, the offseason will likely be interrupted on Dec. 2, when the owners are expected to lock out the players as baseball’s collective bargaining agreement expires. Thus, the Cubs may want to move quickly, especially since they have many needs to address.
The obvious move to address the hole at the top of the starting rotation is to sign left-hander Tarik Skubal in free agency. However, the two-time Cy Young Award winner reportedly wants $400 million, and the Cubs have too many needs to drop that much on one position.
A good fit would be right-hander Freddy Peralta, who enters free agency with real momentum. After struggling in his first season with the New York Mets, Peralta has turned things around since the Tampa Bay Rays acquired him at the deadline, including being named MVP of the American League Championship Series.
Counsell is also very familiar with Peralta, with whom he spent six seasons with the Brewers. Peralta won’t be cheap, as the 30-year-old will likely command a five-year, $125-million contract, but he would still be more economical than Skubal or fellow free agent Michael King. Chicago can't leave this offseason without an anchor atop the rotation given Shota Imanaga, Clay Holmes and Kevin Gausman hitting free agency all the uncertainty surrounding Justin Steele, Cade Horton and Ben Brown.
The Angels front office is in flux now, but it would be wise to call and see if left-hander Reid Detmers is still available. The Cubs almost landed Detmers at this year’s deadline, according to reports.
Detmers, 27, is coming off his best season to date and cannot become a free agent until after the 2028 season. Pitching for the Angels, who had the worst record in the Major Leagues this year, Detmers still went 7-8 with a 3.36 ERA and 1.038 WHIP in 32 starts, striking out 211 in 185 innings.
The Cubs could offer top prospect Josiah Hartshorn, a 19-year-old switch-hitter who finished this season at Double-A, and right-hander Cade Townsend, a first-round draft pick this year. Townsend is the Cubs’ No. 6 prospect.
Detmers figures to have a $7.5 million salary through the arbitration process, with three years of cost control remaining.
The Cubs acquired left-hander David Peterson from the Mets on June 25, and he was solid for Chicago. In 16 games and 15 starts, he posted a 6-2 record with a 3.70 ERA.
Peterson seemingly shouldn’t be the type of pitcher who should bust the budget. However, he may generate more interest than expected as a lefty with a good ground-ball rate, and the Cubs may have to go three years and $39 million to get him. Either way, he's exactly the sort of depth piece this rotation needs.
The Cubs can retain Rea by exercising a $7.5 million option for 2027. His buyout is $1 million, so the 36-year-old right-hander would cost the Cubs just $6.5 million.
That would be a fair price for Rea, who pitched close to league average this year with a 4.34 ERA over 137 innings, split across 19 starts and 15 relief appearances.
The Cubs really need someone to anchor what's been a volatile bullpen for years now. Left-hander Adrian Morejon would be the perfect target on the open market.
Morejon is just 27 and enters free agency after a season in which he posted a 2.83 ERA, 1.081 WHIP and 107 strikeouts in 86 innings and 76 games for the Padres. Signing relievers to long-term contracts is always risky, and the Cubs will need to go to five years and $90 million to land Morejon in a competitive market, but it’s a gamble worth taking.
The Cubs won’t have much more money to spend on the bullpen if they sign Morejon. So, exercising a $2.5 million contract option for 2027 on right-hander Jacob Webb makes plenty of sense.
The 33-year-old right-hander doesn’t profile as an All-Star closer. Yet he led the Cubs with nine saves this season while posting a 3.36 ERA in 67 appearances.
Left fielder Ian Happ and right fielder Seiya Suzuki are both on expiring contracts.
Suzuki is seeking a nine-figure contract, which may be too high for the Cubs to give a 32-year-old. Happ is a career Cub and has expressed a strong desire to stay. The qualifying offer is $23.15 million this year, and the 32-year-old Happ would almost certainly accept it and eschew free agency.
The Cubs would need to fill Suzuki’s spot, and one option could be to trade for the Dodgers’ Teoscar Hernandez. Los Angeles need to make room in the lineup for top prospect Josue De Paula, so they might be willing to trade Hernandez and pay down part of his $22.1 million salary for 2027 in the final year of his three-year, $66-million contract.
The Dodgers would likely put $8 million into a deal, even with a minimal return like reliever Phil Maton, who had a 6.18 ERA this season for the Cubs in 27 games and carries a $6 million salary next season.
Carson Kelly made the majority of the starts at catcher for the Cubs in each of the last two seasons. Kelly has been good, but he also has a club option for next season worth $7.5 million, and the Cubs will have to save a few dollars somewhere.
So the Cubs should pay Kelly the $1.5 million buyout and promote Miguel Amaya to the No. 1 catcher job. Switch-hitting Owen Ayers, who hit 25 home runs in the Minor Leagues last season, is an intriguing backup option and ranked as the organization’s No. 3 prospect.
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