Jack's Take: Time For Chicago Cubs To Go All-In, Trade For A Starting Pitcher

The Chicago Cubs pitching staff took a major hit on April 13 when news broke that left-handed starter Justin Steele would undergo elbow surgery and miss the rest of the 2025 season.

Steele had been a model of consistency, posting an ERA of 3.18 or lower in each of the last three seasons with 119-plus innings. He even finished fifth in NL Cy Young voting in 2023.

The injury put the Cubs in a tough spot. It's typically too early to expect any team to make a big trade in April, but the Cubs also don't want to let their division lead quickly slip away. So far, the contingency plan has been veteran righty Colin Rea, who in two starts has allowed just two earned runs across eight innings.

The Cubs have won both of Rea's starts, defeating the Dodgers and Diamondbacks. Behind Rea, potential starting options down the road include Jordan Wicks, Javier Assad and perhaps even the organization's top pitching prospect Cade Horton. There's something to like about each of those four, but the Cubs arguably should have upgraded the staff even more than they did in the offseason, when it entered the year with Steele, Shota Imanaga, Jameson Taillon, Matthew Boyd and Ben Brown.

That debate is more definitive now that Steele, a borderline ace, is out for the year. The Cubs are off to a strong start, leading the NL Central at 14-10 and two wins behind the MLB-leading Padres and Dodgers with 16 wins apiece. Believe it or not, Baseball Reference gives the Cubs the best chance in MLB to win the World Series at 17.6%.

But in order for the Cubs to really compete in 2025, president of baseball operations Jed Hoyer needs to upgrade the rotation, and likely the bullpen too, through the trade market. Whether by design or factors out of the Cubs' control, that may not happen until the trade deadline in July, and that's OK. But the Cubs are at least one high-end starting pitcher away from becoming a bona fide title contender, and they seem to know that.

Bruce Levine of 670 The Score reported Monday, "the Cubs are already browsing the trade market looking for pitching help." Among starting pitchers, Levine listed Marlins righty Sandy Alcantara, Twins righty Pablo Lopez and Cardinals right-handers Sonny Gray and Erick Fedde as candidates.

The price for Alcantara would likely include outfielder Owen Caissie, the Cubs No. 3 prospect who's ranked No. 50 in the MLB Pipeline, among others, according to Levine. He also mentioned Athletics closer Mason Miller as a potential option to bolster the bullpen, and he would "demand a boatload of talent" in a trade.

There are a few reasons I wouldn't hesitate much to trade Caissie and a few lower-level prospects to get Alcantara or Lopez, for example. First being that Alcantara, the 2022 NL Cy Young winner, is exactly what the Cubs need to compete for a World Series title now and in the future. The 29-year-old is under team control through the 2027 season at a reasonable price of $17.3 million per year through 2026 and $21 million in 2027.

Lopez, 29, may be a slight downgrade in talent, but he's still shown to be very consistent with a career 3.86 ERA and at least 180 innings pitched in each of the last three seasons, including a 2023 All-Star nod and a seventh place AL Cy Young finish. He's also under team control through 2027 at $21.7 million per year.

The second reason has to do with the Cubs' competitive window. Players like Dansby Swanson, Ian Happ, Seiya Suzuki, Shota Imanaga and Jameson Taillon are in their early 30s. Nico Hoerner, Kyle Tucker and Michael Busch are in their late 20s. From and age and contract standpoint, Hoyer has lined things up for 2025 to be one of the Cubs' best chances to compete.

That's especially true if the Cubs do not extend Kyle Tucker, which is a whole different conversation. If this does turn out to be the only year Tucker is in a Cubs uniform, they should be doing everything in their power to maximize having an MVP candidate. Acquiring two additional seasons of Alcantara and Lopez would indirectly help in replacing Tucker.

The window extends if the Cubs decide to shell out the $500 million or so it could take to keep Tucker. And in that case, trading Caissie or fellow outfield prospect Kevin Alcantara becomes even less of a loss because the outfield would be locked up for the long term with Happ, Pete Crow-Armstrong and Tucker. A trio of Alcantara, Steele and Imanaga at the top of the 2026 rotation would put the Cubs in perhaps even better position than they're in now to compete.

The Marlins (9-12), Twins (7-15) and Athletics (10-12) seem to be the perfect trade partners, given their level of competitiveness. Though the price will be high to acquire a front line starter or high-leverage reliever, the timing is right for the Cubs to go all-in.

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