The Chicago Cubs will be buyers at the trade deadline for the third time in the last four seasons, which means president Jed Hoyer will be active again.
Just how active is anyone’s guess, with the Cubs holding onto the top wild-card spot before Tuesday’s 11-2 win over the Detroit Tigers, but six games behind the Milwaukee Brewers in the National League Central.
If the status quo plays out, they’ll host a best-of-three wild-card series at Wrigley Field in October, just like last year, while the Los Angeles Dodgers and Milwaukee Brewers get byes again.
“I think you have to go into the deadline thinking about it analytically,” Hoyer said last Friday. “Thinking about OK, getting a bye is effectively winning a series and weakening your opponent in the next series. That’s a really big deal. So if the odds say that you can do that, then that’s a different equation than if not. I think you have to be aware of those things.”
The Cubs have a 79% chance of making the playoffs, according to FanGraphs, but only an 8.6% chance of winning the division and a 4.8% chance of a first-round bye.
In a fantasy world that only exists on the internet and selected Cubs blogs, the team will be in on Tarik Skubal, Mason Miller, Joe Ryan, Josh Hader or maybe another elite pitcher who may be available for a slew of top prospects.
In the real world we’ve been living in over the last four years of the Hoyer regime, the Cubs are more likely to be in on Freddy Peralta, José Soriano, Casey Mize, Brooks Raley or a few other pitchers who’ve dealt with injuries or recent struggles and won’t cost them an arm and a leg, prospect-wise.
But who knows?
Perhaps the 2016 reunion weekend will spur Hoyer to make a big, bold move at the Aug. 3 deadline. Maybe Chairman Tom Ricketts will give Hoyer the leeway to go for it, as he did last January with the signing of Alex Bregman to a five-year, $175 million deal while the Bears were mounting an epic comeback against the Green Bay Packers in the playoffs.
Either way, the spotlight will be on Hoyer, and to a lesser extent Carter Hawkins, the general manager who generally stays out of sight.
Here’s a brief reminder of what they’re done the last three deadlines:
In 2023, Hoyer was a likely seller until the team went on an eight-game win streak in late July, pulling to within 3 1/2 games in the Central and getting in the thick of the NL wild-card chase. Instead of dealing Cody Bellinger and Marcus Stroman, Hoyer went the other route and acquired third baseman Jeimer Candelario and cash from the Washington Nationals for prospects Kevin Made and DJ Herz, along with reliever José Cuas from the Kansas City Royals for outfielder Nelson Velázquez.
Neither Candelario nor Cuas made a big impact, but the Cubs were in position for a wild-card spot in mid-September until a 4-11 stretch did them in. The collapse cost manager David Ross his job, even as Ricketts told reporters on the final day of the season: “Rossy had a great season, and the players play hard for him. He’s our guy.”
Well, that was technically true at the time. But soon Craig Counsell was his guy, agreeing to a five-year, $40 million deal to work his magic in Chicago.
In 2024, the Cubs flopped in May after a strong start and had the fourth-worst record in the National League at the deadline, ending any potential drama. Hoyer dumped Christopher Morel on the Tampa Bay Rays in a deal that netted third baseman Isaac Paredes, who was later part of the offseason deal that brought in Houston Astros star Kyle Tucker, a one-and-done guy. The only other move was dealing Mark Leiter Jr. to the New York Yankees, but no one really cared.
Last year was Hoyer’s big opportunity to channel his inner Theo Epstein, with the Cubs neck-and-neck with the Brewers in the Central and looking at a chance to clinch that coveted first-round bye. Ricketts handed Hoyer an extension three days before the deadline, showing faith in his guy, who had gone playoff-free in his first four seasons.
Once again, getting pitching help was the primary goal, but Hoyer wound up getting a soon-to-be-injured starter in Michael Soroka, two leverage relievers in Andrew Kittredge and Taylor Rogers, and a utilityman in Willi Castro. He managed to keep his top prospects — Moisés Ballesteros and Owen Caissie — and rookie Matt Shaw.
“The asking price we felt like was something that we couldn’t do to the future,” Hoyer said after the deadline passed. “In the end, the asking price on those guys would have been so detrimental to our future that we decided against it.”
Hawkins later defended the moves to ESPN, telling reporter Jesse Rogers: “Teams are trying to find that guy that can lock down the eighth or ninth inning, but that also costs a lot. That costs a lot of future wins. We have a responsibility to the 2025 Cubs but also the 2032 Cubs. That’s not always popular in the moment, but it’s decisions we have to make.”
That didn’t go over well with Cubs fans, who weren’t really thinking about 2032 at the time.
Two weeks after the trade deadline, the Cubs were nine games behind the Brewers and spent the rest of the season focusing on the wild card. They wound up beating the San Diego Padres at Wrigley before losing the National League Division Series to Milwaukee in five games. The season was considered a stepping stone to better things in ’26.
None of the four deadline acquisitions returned, and Kittredge was even sent back to Baltimore, where the Cubs got him. Caissie was dealt after the season to the Miami Marlins to bolster the rotation with the addition of Edward Cabrera, who currently remains on the 15-day IL and is not close to returning. Ballesteros is trying to rediscover his stroke at Triple-A Iowa, and Shaw was made into a utilityman when the Cubs signed Bregman. He’s also out for a while with a wrist injury.
Now we’re back to watching what Hoyer will do next. He has always been an advocate of “intelligent spending,” which is … what exactly?
“Obviously there’s a danger in free agency of committing a lot of years and a lot of dollars to players in sort of a decline phase of their career,” Hoyer said back in ’21 when he started the reboot. “You always have to be mindful of what the biggest value is in that contract. Free agency is valuable. Free agency is also dangerous.”
So here we are, with two weeks to go until the deadline and 2032 still a long way away.
It’s Hoyer’s most crucial trade deadline to date.
Keep him in your thoughts.
