Cubs Hit With Scary Ultimatum on 23-Year-Old Prospect After Manager Throws Away Plans Amid Shaky Stretch

September baseball is here, and so are the expanded rosters! For the Chicago Cubs, that means a couple of fresh faces, and one of the familiar names is Kevin Alcantara. The 23-year-old outfielder, and Chicago’s no. 5 prospect, is back in the major league as a September call-up for the second time in a row.

But this time, it feels different, and it is, given that a lot more is at stake. The Cubs are not just playing out the string; they are, for the first time since 2020, chasing their first postseason berth. And Craig Counsell has already, for now, thrown away the word “cautious” from his dictionary. He mentioned to Marquee Sports’ Bruce Levine that Alcantara will get the nod in center against left-handed pitchers.

This is a bold move that shifts Pete Crow-Armstrong out of the guaranteed reps and forces the Jaguar into the role, which has real consequences. But given Alcantara has been insane in the minor league with .319/.394/.604 with six bombs and a .998 OPS—it’s easy to see why Counsell’s ready to test the waters. However, there is some support for this decision.

Keith Law isn’t so optimistic; he, in fact, gave a scary ultimatum, saying, “Bending the rules a little bit here, as ‘The Jaguar’ came up last year for 10 at-bats, so this won’t be his MLB debut. This season, the Cubs’ top prospect hit .266/.349/.470 in his first full year in Triple A, improving as the season went on—but he struck out 29.8 percent of the time, a result of his 6-foot-6 frame and the big hack he takes. …” However, for Law, the real fear is that big league pitchers will feast on him with breaking stuff, given his 40% whiff rate against it in the minors.

Plus, let’s not forget to make room; the Chicago Cubs also sent down Owen Caissie, who is another top prospect who himself got struck out nine times in just 25 plate appearances during his MLB stint. So, Alcantara can fall into the same well. So that’s the tightrope that Chicago is walking on. On one hand, Alcantara’s power makes him a weapon, but his strikeout issues and struggles are not something to discount.

For now, though, Alcantara is living the dream—going 1 for 3 with a run in his first start Tuesday against the Atlanta Braves before Pete Crow-Armstrong closed it out in the center. The reality is that the Cubs’ playoff hopes are now hanging, and Alcantara’s ability to stick can make a huge difference.

The real reason that made Carlos Santana choose the Cubs

The Cubs weren’t just relying on prospects, given the stakes are so high, and so the front office loaded up on some veteran help too. So before the postseason eligibility deadline, Chicago added Carlos Santana and Aaron Civale. But here is the twist—Santana’s decision to join the Chicago Cubs was not about the contract or numbers; it all came down to a single phone call.

Just ahead of his first game with the Cubs, Santana opened up about how it all went down. After being released by Cleveland, he admitted that Craig Counsell was the only manager who actually picked up the phone to give him a call. And because of their history, that call meant everything to him. “[Counsell] brought me to Milwaukee [in 2023], and I and I had a very good relationship. The day before I came here, he called me and said, ‘I need you here.’ So I said, ‘Yes, I’m not thinking twice.’ He was the only manager that talked to me. He showed me a lot of respect. That’s why I came here,” Santana mentioned to MLB.com.

That level of connection and respect shows just how much leadership really matters in MLB. For Santana, it wasn’t about the team needing depth; it was about the trust that Craig Counsell had in him. And now, the 38-year-old is ready to make an impact on the Cubs’ postseason push. Moving ahead, he is expected to see plenty of at-bats against the left-handed pitchers. Given that Michael Busch is hitting just .195 against southpaws, Santana’s ability to handle lefties and also give steady defense makes him a crucial add-on.