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Cubs boost potential playoff roster with September additions

Jared Wyllys Avatar
September 1, 2025
USATSI 26926696

It’s September, which means it’s time for the final push. If the season ended now, the Cubs would have the top wild card spot, which means they would host the Padres for a three-game wild card series. With 23 games remaining in the season, there is still time to leapfrog the Brewers for the division title, but the most statistically probable scenario is that the Cubs will be in the playoffs, but not as National League Central champions.

Happy with that or not, it means that as we enter the last month of the regular season, teams can make the final additions to their rosters to use in the postseason. Any player signed after Monday noon can play in September, but he wouldn’t be eligible for a playoff series roster.

The Cubs made a few moves leading up to the September 1 deadline, most notably signing veteran Carlos Santana to a major league contract. Santana, 39, has played 16 seasons in the majors, most of them with Cleveland. Santana was released by the Guardians on August 28; in 116 games for Cleveland this year, Santana batted .225 with 11 home runs and 52 runs batted in.

Santana said a couple of teams expressed interest in signing him after the Guardians released him last Thursday, but the Cubs had the most appeal because of the talent on the roster and the experience of playing in Chicago, and because of all the teams showing interest, Craig Counsell was the only manager who reached out to him directly about coming to play for his team.

Santana’s most important value will likely be his switch-hitting and ability to spell players in multiple positions, along with the intangible benefit of his extensive postseason experience. Santana was, of course, on the losing side of the 2016 World Series, but he has also appeared in the playoffs in five other seasons. In all, Santana has 129 postseason plate appearances.

His role for the Cubs over the next month — and beyond — will be one that will likely have to require Santana to be very flexible.

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“Whenever the team needs me, I’ll be open,” Santana said. “If they want me to play whatever position — third base, outfield — I can do it. I come here to help [to win] a championship. Before I retire, I want to [be] a champion.”

Santana has a sterling reputation around the baseball world, and his veteran presence is quickly paying some dividends. He said Michael Busch approached him almost immediately about working together on his first base defense.

Team president Jed Hoyer said there were conversations about trading for Santana at the July 31 deadline, but a deal didn’t get done. Given the Cubs’ struggles against left-handed pitching, the front office had Santana on their radar because of his .819 career OPS against southpaws.

Along with Santana, the Cubs claimed pitcher Aaron Civale from the White Sox over the weekend, and they recalled Kevin Alcantara from Triple-A Iowa and optioned Owen Caissie back to Iowa. Civale started the season with the Brewers and was traded to the White Sox on June 13 for Andrew Vaughn. He was used out of the rotation for both teams and has a 5.26 ERA in 18 starts, but the expectation is that Civale will provide mostly long relief for the Cubs.

Hoyer said there weren’t a lot of arms placed on the waiver wire last month, but Civale was also a pitcher they had discussed making a move for a month ago. Both players are with the Cubs for the final month because Hoyer and the rest know that while they have been good enough to be 19 games above .500 going into September, the final weeks of the season and then the playoffs will demand a lot more.

“I do think we’re in good position, but I also feel like adding is always valuable when you know you’re getting to this position where guys have tendencies to get tired and you may want to give guys a little bit of rest,” Hoyer said.

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The Alcantara-for-Caissie swap is as much for Caissie’s long-term benefit as it is getting the right mix of players on the bench, something that has been a struggle for the Cubs all season. Not playing every day like they are used to presents a challenge for young guys, as does the reality of handling high-pressure situations.

“It’s really hard because when you think about having prospects up here, the bench is really difficult because they’re not used to that role,” Hoyer said. “Those young players, you’re thinking about ‘How is that guy going to respond if he’s taking an at-bat against an eighth inning guy and he hasn’t played in three days?’

“So I do think it’s challenging in that way, so that’s why oftentimes veteran players that have been through the battles more often are helpful on the bench.”

The trades made at the end of July are often made with the second half of the season in mind, whereas waiver claims and signings like Santana are about shoring up the roster for September and beyond. The Cubs have had a bit of a strange season; they are close to 20 games above .500 but still trail in the NL Central by half a dozen games because the Brewers have been winning at an otherworldly pace since the beginning of June. The Cubs are also benefiting wins and losses wise from two very good months at the beginning of the season, when they went 36-18 through the end of May.

Since then, they have played five games above .500, which isn’t bad, but that has left them locked in a perpetual state of being too far behind the Brewers to compete for first place while also not securely holding on to the top wild card spot. They’ll need a red-hot September to change either of those things.

Additions like Santana and Civale won’t necessarily make the difference by themselves, but whatever playoff spot the Cubs hold, both players will help the team better handle October baseball.

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