After seeing their division rival walk away with the World Series crown, the Chicago Cubs feel even more pressure to return to the top of the NL Central. And ot will not be easy.
They have a lot of work to do to compete with Milwaukee, let alone several other high-powered NL teams. The farm system needs drastic improvement, and the Cubs need to revamp the entire pitching infrastructure. Both the starting rotation and the bullpen are bound for a significant overhaul this winter.
Several Cubs players have already declined their player options , including Matthew Boyd and Clay Holmes. Will the Cubs re-sign some of their free agents? If not, then they will have to make some moves in free agency. Everyone is focusing on the top names, but what about some underrated signings? In other words, free agents who can improve the overall depth of this team.
Let's try to pick out four under-the-radar players the Cubs can target in the coming months!
Sep 7, 2026; Los Angeles, California, USA; Los Angeles Dodgers third baseman Max Muncy (13) slides to beat the throw to Cincinnati Reds catcher Tyler Stephenson (37) and score during the eighth inning at Dodger Stadium. Mandatory Credit: Kiyoshi Mio-Imagn Images | IMAGN IMAGES via Reuters Connect
Everyone knows that pitching will be the focus, but there are other positions that the Cubs need to add, including catcher. Carson Kelly is set to become a free agent, and the Cubs will have Miguel Amaya at their disposal. Will they also call up their top prospect Owen Ayers? That is a strong possibility, but it wouldn't hurt to have a quality starter.
Enter Tyler Stephenson!
The former Reds backstop would immediately become the Cubs' starting catcher and solve one of the biggest offseason issues. A tandem of him and Amaya would arguably be an upgrade at the position. He's only 30, and his contract projection isn't a bad price. It's something the Cubs can easily afford. Funny enough, Jim Bowden of The Athletic did an article on the top 40 free agents and said that the Cubs were one of the best fits. He projected that Stephenson could get 2 years for $16 million.
If you're the Cubs, you take that opportunity. Stephenson is one of the better defensive catchers in the game. He ranked third-best in the league in pitch blocking and had a 78.0 percent success rate with the ABS challenges. Why not add a great defensive catcher to an already elite defense?
It's also not as if Stephenson isn't a capable hitter. He holds a decent .757 OPS over his career and has hit 13+ homers in four straight seasons. Overall, there is a reason the Reds have kept him behind the plate for so many years, as he's been remarkably consistent both at and behind the plate.
Sep 24, 2026; West Sacramento, California, USA; Houston Astros pitcher Bryan Abreu (52) celebrates after the game against the Athletics at Sutter Health Park. Mandatory Credit: Sergio Estrada-Imagn Images | IMAGN IMAGES via Reuters Connect
The Chicago Cubs need late-inning eaters. They lack setup guys who can provide consistency in high-leverage situations. Adding someone with significant playoff experience and championship acumen also helps tremendously!
If the Cubs added Bryan Abreu to the bullpen today, he would arguably be their best arm. Pairing him with Ryan Zeferjahn as their two setup guys would give them a huge upgrade, as well as two arms with strong velocity.
After getting off to a slow start, Abreu bounced back and went 6-4 with a 3.73 ERA and 80 strikeouts. Abreu is a setup man who can also fill in at closer if needed. But ideally, you make him a setup guy. The 29-year-old had a nearly 30.0 percent K rate this season, which included a whiff rate that ranked in the 97th percentile, per Baseball Savant .
At the end of the day, Jed Hoyer knows that he needs more proven arms in his bullpen. Abreu wouldn't come cheap, but he would fill a necessary void for a team with championship aspirations.
Aug 25, 2026; Phoenix, Arizona, USA; Chicago Cubs pitcher Clay Holmes against the Arizona Diamondbacks at Chase Field. Mandatory Credit: Mark J. Rebilas-Imagn Images | IMAGN IMAGES via Reuters Connect
Ideally, if the Cubs can acquire Tarik Skubal, Michael King , Freddy Peralta, or Reid Detmers, that would be a huge upgrade to their rotation. There's no guarantee of getting those guys, however, so why not bring back some familiarity and stability to the rotation?
Re-signing Clay Holmes should be a priority for the Cubs. With Kevin Gausman likely returning to the Toronto Blue Jays, Holmes can be a realistic fifth option. They traded away their top prospect, Jefferson Rojas, to acquire him.
Holmes has playoff experience, is reliable, and, on a championship-caliber team, can be your fifth starter or a long reliever/6th option. Adding Holmes back to the mix would benefit both parties, as it would be one less hole to fill on the roster and the cost would not be too high. In 2026, he went 6-8 with a 3.29 ERA and struck out 78.
Aug 5, 2026; Seattle, Washington, USA; Seattle Mariners designated hitter Taylor Ward (27) reacts to hitting a single during the third inning against the Detroit Tigers at T-Mobile Park. Mandatory Credit: Steven Bisig-Imagn Images | IMAGN IMAGES via Reuters Connect
There's a lot of uncertainty in the Cubs' outfield. With Ian Happ and Seiya Suzuki both set to become free agents, the Cubs have to decide how they want to approach it. When we consider that the focus is mainly on pitching, will they let those players walk and shift their focus to guys who can be reliable but not pricey?
Taylor Ward is a versatile outfielder who can play both corner spots and hit for power. He brings a veteran presence and is projected to receive a cheaper deal on the open market. Last year he struggled, so the Cubs can take a chance and see if he can have a redemption season. He hit .225 with 7 home runs and 37 RBI's.
Yes, Ward isn't known as a dominant player, but what stands out about him is his discipline at the plate. His ability to walk and create scoring opportunities can give the Cubs more chances to improve their already top offense in the league. Ward can be that glue guy who does all the little things and occasionally hits a ball out of the park.
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This article was originally published on www.si.com/mlb/cubs/onsi as 4 Under-the-Radar Free Agents the Chicago Cubs Should Target .
