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Column: As trade deadline nears, the spotlight grows on Chicago Cubs President Jed Hoyer

July 20, 2025 by Chicago Tribune

Midway through Jed Hoyer’s latest Ted Talk on the July 31 trade deadline, the thought occurred that maybe the Chicago Cubs president should throw his phone into Lake Michigan and sit this one out.

Would the Cubs be OK in October without another starter, another “out-getter,” and maybe an offensive-oriented third baseman?

Has this team earned the benefit of the doubt after four months of playing a brand of baseball we haven’t seen on the North Side since pre-pandemic days?

Those are questions Hoyer must ask himself as he explores deals in the final laps before the deadline.

For well over a month now, Hoyer has been updating the media, podcasters and his Winnetka Starbucks baristas about his desire to add pitching at the deadline. It made sense in early June, with Justin Steele out for the season and Shota Imanaga on the IL, and makes even more sense now with Jameson Taillon out for several more weeks.

The Milwaukee Brewers won’t go away, and their rotation is just getting stronger with the addition of rookie phenom Jacob Misiorowski.

Hoyer provided another update Friday morning in the Cubs dugout, spending nearly 25 minutes answering questions from radio reporters — and occasionally print reporters — on his plans to improve a team that would go on to beat the Boston Red Sox that afternoon and wake up Saturday with the best record in the National League.

I’ve managed to attend about a half-dozen of these dugout briefings, at which Hoyer generally says the same things in different ways without revealing anything particularly newsworthy.

It’s an art form he learned from his mentor, Theo Epstein, who learned how to be a front office executive as a 21-year-old public relations intern in San Diego, studying under the late Kevin Towers, the godfather of general managers.

Hoyer eventually would take over for Towers in San Diego before rejoining Epstein in Chicago to help execute the Cubs rebuild. Now he’s in the big chair, in the final year of his contract, trying to write a happy ending to a special season.

Cubs outfielder Owen Caissie runs drills with other players on the first day of full-squad workouts during spring training at Sloan Park on Feb. 14, 2025, in Mesa, Ariz. (Armando L. Sanchez/Chicago Tribune)
Cubs outfielder Owen Caissie runs drills with other players on the first day of full-squad workouts during spring training at Sloan Park on Feb. 14, 2025, in Mesa, Ariz. (Armando L. Sanchez/Chicago Tribune)

Hoyer noted that the big deals usually come down to the last days of July, when the sellers become more obvious and more players become available. “It’s the nature of the deadline,” he said. Hoyer added there are no “untouchable” prospects in the Cubs’ system, (we’re looking at you, Owen Caissie) and that he’s not thinking about the makeup of the team in October. The goal is “winning as many games as possible” to get there, and go from there.

The Brewers, he predicted, are not going to fade away, while the Cubs can control only what they can control.

Cliches aside, it seems a given Hoyer will acquire at least one prominent starter after all the buildup. The lineup can survive a weak-hitting No. 9 hitter, but the rotation obviously needs a lift with Taillon out.

Matthew Boyd, whose workload is being monitored, and Imanaga, who started Saturday and is still building back after a long rehab from his hamstring injury, are the likely starters for Games 1 and 2 of any postseason series. Colin Rea consistently has given the Cubs five good innings, and rookie Cade Horton has been impressive with a few blips. The fifth starter’s spot remains in flux after Chris Flexen’s spot start in Yankee Stadium, and manager Craig Counsell has not revealed his rotation plans after Saturday.

Boyd said he trusts Hoyer, though he also pointed out “we have one of the best records in baseball, these guys that currently are in the clubhouse.” That seemed like a call to keep the  status quo.

“Whatever moves he does make or does make, we know it’s going to be best,” Boyd said. “It’s also tough to talk about that (trade) stuff, because when you talk about someone coming in, that means someone has to go out, and the clubhouse is a family. And the guys that got us to this point are the guys that are in the clubhouse.

“It’s always an interesting issue. It’s above my pay grade. But we’re got full trust in him, he’s one of the smartest guys I know.”

Matthew Boyd #16 of the Chicago Cubs looks on during All-Star Workout Day at Truist Park on July 14, 2025 in Atlanta, Georgia. (Photo by Kevin C. Cox/Getty Images)
Cubs pitcher Matthew Boyd looks on during an All-Star workout at Truist Park on July 14, 2025 in Atlanta. (Kevin C. Cox/Getty Images)

A first time All-Star at age 34 who declined to pitch in the game to rest for the second half, Boyd already has given the rotation a shot in the arm. Due to all the starters’ injuries, he has become the accidental ace through 97 games and an inspiration to geezers of all stripes for his perseverance from injuries and various setbacks.

In an article for SportsSpectrum.com in 2024, Boyd credited his faith, writing: “He has come through better than I could have imagined, and I know He’s going to do it again. But I’d be lying if I said I didn’t often ask Him, ‘When’s it going to happen?’”

It started to happen in August when he returned to help the Cleveland Guardians into the postseason and has continued this year with the Cubs. But Boyd already is at 111 2/3 innings in 2025 after throwing 61 1/3 combined innings last season after missing more than a year recovering from Tommy John surgery.

Boyd told me there’s no set plan or innings limit on him but said Counsell and pitching coach Tommy Hottovy told him if there was a chance to “not push you harder in a game,” they’ll always take it. Boyd’s health will be a key to the Cubs’ chances in October.

“It’s communication on my end and back and forth,” Boyd said. “It’s got to be an open line. That’s how you make it work.”

The oft-cited theory that injuries and regression are often a result of teams overextending the pitcher’s workload from one year to the next is one that modern-day baseball executives are forced to deal with on a daily basis. Not all teams think alike.

Last year, White Sox general manager Chris Getz put a governor on Garrett Crochet’s workload, limiting their ace to four or fewer innings in his final 13 starts, making the plan a priority over winning those games in what resulted in a record 121-loss season. Crochet, who starts for the Red Sox on Sunday at Wrigley Field, entered Saturday leading the majors in innings (129 1/3) and strikeouts (160).

At the All-Star Game last week in Atlanta, Crochet told me he appreciated the special treatment from Getz and pitching coach Ethan Katz, which allowed him to remain a starter while increasing his trade value for the White Sox rebuild.

“I think it set me up for a strong 2025, that’s for sure,” Crochet said of Getz’s plan. “I’ve got nothing but good things to say about them.”

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Hoyer, however, is skeptical of putting such limits on his pitchers, believing individuals have different thresholds for fatigue. Some pitchers don’t merit having “random restrictions” placed on their workload, he said, while stressing they’ll still monitor Boyd closely and won’t risk an injury.

“It’s hard because people always try to put all these rules in place about guys coming back (from injuries),” Hoyer said. “And we realize we’re just not very good at this as an industry, honestly. That’s the reality. We monitor his strength, his fatigue really carefully, and if we see any negative signs, we have to operate with that in mind.

“We’re not going to do anything to put him at risk, but if he continues to be strong and show no fatigue …”

Hoyer pointed to the Cubs’ plan last year to give Imanaga more rest in the second half. But the Cubs were out of contention then, and the games had less importance. Now everyone is paying attention to the Cubs.

“It’s a little harder right now with Jamo hurt and (Javier) Assad hasn’t pitched and Steele went down,” Hoyer said. “It’s harder to do that, but the hope potentially is that if we can acquire pitching that allows us to do more of that, we can keep guys fresh.”

The spotlight on Hoyer grows as the deadline nears. His moves last winter and spring put the Cubs in this position, and the moves he will or won’t make the next two weeks could determine his future.

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