3 free agents Cubs must sign for Craig Counsell to get revenge on Brewers in 2025

The Milwaukee Brewers clinched the NL Central on Wednesday, effectively eliminating the Chicago Cubs from postseason contention in the process. This feels an awful lot like last season, when Chicago put together a torrid stretch after the All-Star break, but couldn't quite get over the hump in the final weeks.

Chicago made quite the spectacle of hiring Craig Counsell away from the Brewers last winter. Jed Hoyer and the front office tossed David Ross under the bus in record time, moving on without much of an effort at cordiality. Counsell was signed to the largest managerial contract in MLB history. It reset the market and, in theory, it reset the division.

The Brewers turned to Pat Murphy, Counsell's former bench coach and somebody who has been around the game of baseball for ages. Point blank, Murphy has out-coached Counsell this season. We can give Counsell the benefit of the doubt — it's a new situation and Chicago's personnel choices haven't panned out — but when you're inked to a historic contract, it's only natural to expect immediate results.

Counsell was lauded for his analytical mind and penchant for manipulating matchups in Milwaukee. With the Cubs, he has let the bullpen come apart at the seams while frustrating fans with strange lineup tweaks. Take for example his ongoing commitment to pinch-hitting Patrick Wisdom for Michael Busch in critical spots when Busch is far and away the more dependable bat, even against left-handed pitchers.

Something has been off from the start. If next season isn't materially better, that will lead to some uncomfortable questions on the North Side. Here are a few free agents Chicago should target to help Counsell's cause in 2025.

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3. CP Kenley Jansen would anchor the Cubs' needy bullpen

The Boston Red Sox will have several tough decisions to make this winter. That includes the free agency of veteran reliever Kenley Jansen, who could command a pretty penny at 36 years old. This has not been Jansen's most dominant campaign, but he continues to produce at a high level. He has a 3.42 ERA and 1.10 WHIP, striking out 61 across 52.2 innings of action. Jansen has 27 saves to his name this season.

Chicago's last highly-touted veteran bullpen addition didn't pan out (Hector Neris), but Jansen brings an impressive resumé to the table. He's a four-time All-Star, including last season, and he finished top-five in Cy Young voting back in 2017. At his peak, Jansen was on the shortlist of best closers in baseball.

He may not win the closing job outright for Chicago, but late relief pitching has been a mess and a half for the Cubs this season. Jansen at least provides some measure of stability and a credible leadship voice in the clubhouse. This is not a Craig Kimbrel situation; Jansen is still in the 87th percentile for strikeouts with an expected batting of average of only .217, per Baseball Savant.

The Cubs' 2024 campaign probably looks far different with a stable ninth inning option in the bullpen. Jansen can't be the only reliever Chicago signs — this needs to be a complete teardown and reconstruction — but he's a flashy name for a reason, and one has to imagine he would drastically improve the Cubs' standing in the NL Central.

2. SP Roki Sasaki brings major upside to the Cubs rotation

Among the most anticipated free agents of the 2024-25 cycle is Roki Sasaki, the 22-year-old Japanese phenom who could upstage Yoshinobu Yamamoto and Shota Imanaga just one year later. Because of his age, the fireballing righty won't be eligible for the same long-term megadeal that Yamamoto signed. He will instead be paid in line with standard MLB prospects, which adds another layer of interest to Sasaki's free agent profile.

The Cubs were never a real threat for Yamamoto because of money. Sasaki is arguably a better prospect and he doesn't come with the burden of a 12 or 13-year contract worth north of $300 million. Chicago can remove financials from the equation, instead pitching Sasaki and his reps on the benefits of donning a Cubs uniform and performing in historic Wrigley Field for 81 games per season.

Imanaga is a compelling point in the Cubs' favor here. He transitioned to the MLB game seamlessly, earning a quick All-Star berth and emerging as Chicago's most productive frontline ace. More than that, Imanaga can operate as a mentor for Sasaki, aiding him as he adjusts to life in America and the unique challenges of pitching on the MLB stage.

With triple-digit heat and prodigious command over his pitch arsenal, Sasaki has the potential to contribute from day one and for more than a decade to come. Chicago has been very openly scouting Sasaki this season, with Jed Hoyer personally making the trip to watch him perform. This would qualify as one of the most consequential Chicago free agent acquisitions in recent history.

1. SP Corbin Burnes joining Cubs would be Brewers worst nightmare

The Brewers dealt Corbin Burnes to the Baltimore Orioles last offseasin in a blatantly proactive move. Burnes was entering the final year of his contract and there was no way the small-market Brewers would pony up the cash necessary to retain Burnes as a free agent. Now, there are similar questions about whether or not Baltimore can compete financially for Burnes this winter.

A client of infamous agent Scott Boras, Burnes is expected to squeeze a competitive free agent market for the highest possible dollar value. Your standard major-market heavyweights, such as the Yankees, Mets, and Dodgers, are all expected to take interest in the 29-year-old Cy Young candidate. The Cubs, however, are among the more logical destinations, assuming Jed Hoyer and the front office can get over the financial hump necessary to land Burnes.

There's a good chance Burnes rakes in $200 or $300 million-plus this winter. That is more than Chicago typically spends, but this is also a unique case. Burnes is perhaps the most dependable starting pitcher in baseball. He has finished top-10 in Cy Young voting each of the last four seasons, winning in 2021. He's about to make it five straight top-10 finishes.

Through 30 starts this season, Burnes has a 14-8 record with a 3.06 ERA and 1.12 WHIP. He has been the top-line ace previously missing from Baltimore's arsenal. There is a solid chance we see Burnes pitching deep into the playoffs this October, which would only add to the frenzy to sign him in free agency.

Aside from Chicago's general need for better pitching, Burnes obviously has a special connection to the Brewers organization and his former manager, Craig Counsell. That connection could tempt Burnes to consider Chicago, and it could lead to what is pure nightmare fuel for the Milwaukee fandom. Watching Burnes trot out to the mound in a Cubs uniform every fifth game would be torture for Brewers fans, which would make it doubly enjoyable for the Cubs faithful.