While Chicago Cubs President Jed Hoyer spoke to reporters last week about being in the “information-gathering stage” before the July 31 trade deadline, his protege, Boston Red Sox chief baseball officer Craig Breslow, was already a step ahead.
Breslow and San Francisco Giants President Buster Posey executed the season’s biggest shocker Sunday, with the Red Sox sending slugger Rafael Devers to the Giants for four players in a blockbuster that busted baseball’s norms.
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The deal ended a monthslong soap opera in Boston that began with moving Devers to designated hitter to accommodate the signing of third baseman Alex Bregman, whom the Cubs failed to reel in due to budgetary limitations. Devers subsequently became disgruntled over being treated like an employee and not a superstar.
With a less-than-spectacular return for one of the game’s best left-handed hitters, Breslow opened himself up to the kind of harsh criticism that fuels Red Sox Nation, baseball’s angriest fan base. He’s being compared to Nico Harrison, the Dallas Mavericks general manager who traded Luka Dončić to the Los Angeles Lakers.
The negative feedback Breslow is receiving reminds me of the general reaction to Hoyer trading fan favorites Anthony Rizzo, Kris Bryant and Javier Báez at the 2021 trade deadline. The Cubs received a boatload of prospects no one had heard of, starting the rebuild that couldn’t be called a rebuild.
Nearly four years after that flurry of deadline deals, you seldom hear a discouraging word about Hoyer, even though only one of those prospects, Pete Crow-Armstrong, has become a productive major-leaguer. The players Hoyer dealt never have rediscovered the same kind of success they enjoyed in Chicago, and eventually new stars filled the void, including Crow-Armstrong, Kyle Tucker and Shota Imanaga.
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The rebuild that couldn’t be called a rebuild has morphed into a viable pennant contender in Year 4, just as Hoyer’s contract is ending.
The Cubs will bring a 5½-game lead in the National League Central over the second-place Milwaukee Brewers into Tuesday’s opener of an important — but not make-or-break — series at Wrigley Field. It could tighten the race, or it could give the Cubs more breathing room as they await Imanaga’s return from the injured list. More breathing room might mean less urgency to make a deal, though we’ll have to wait and see.
Hoyer has told reporters, podcasters and probably the baristas at his Winnetka Starbucks that he will be seeking pitching help at the deadline. No surprise. But he also cautioned that teams generally don’t make major deals at this juncture, nearly seven weeks before the deadline. Waiting longer means more players will become available — a time-honored trade-deadline maxim.
Then Posey casually nuked that maxim Sunday, showing Hoyer and the rest of baseball how backward it is to wait until the last minute to try to improve your club. Taking on the remaining $250 million or so of an unhappy superstar’s contract wasn’t a concern, much like Golden State Warriors GM Mike Dunleavy Jr. adding malcontent Jimmy Butler at the NBA trade deadline.
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With the acquisition of Devers, Posey put the pressure on all teams, including the Cubs, to show a little urgency.
Hoyer could be acting out of self-preservation at the deadline of what might be his final shot in Chicago. Or maybe he knows something we don’t know. Cubs Chairman Tom Ricketts likes continuity and didn’t even consider going outside the organization when Theo Epstein left after the 2020 season. At this point, not giving Hoyer an extension would be considered an upset.
Either way, four playoff-free seasons after succeeding Epstein, Hoyer’s era is at a crossroads.
His offseason moves have mostly panned out, despite missing out on Bregman — a deal Epstein reportedly had a part in as a Red Sox minority owner and special adviser and BFF to Red Sox President Sam Kennedy.
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Tucker’s bat has solidified the lineup. Starting pitcher Matthew Boyd has more than made up for Imanaga’s absence while he rehabs his hamstring injury.
The bullpen got older yet surprisingly better with castoffs such as Brad Keller, Drew Pomeranz and Caleb Thielbar stepping in and Ryan Pressly turning things around from a dreadful start. It has been the best relief corps in baseball over the last month. Old and in the way? Nope. Under bullpen coach Mark Strittmatter, they’ve gradually become golden oldies, forcing younger arms to wait their turn at Triple-A Iowa.
Manager Craig Counsell has pushed all the right buttons, when he’s not getting ejected, and Hoyer’s stone-cold firing of David Ross is now a distant memory.
Ricketts could announce an extension at any time but doesn’t seem to be in any big rush. Maybe he’s waiting to see what Hoyer does with his allotted budget at the deadline, hoping for an inexpensive fix instead of a shoot-for-the-moon trade.
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“Hope is not really a strategy,” Counsell said recently in Detroit. He was referring to the idea of hitters waiting on Tigers ace Tarik Skubal to make a mistake, though it also applies here. Hoping the Cubs have enough to make the postseason is no longer an option. The Devers trade — aka “Posey Rule 2.0” — suggests it’s time to ignore the old, unwritten rules of the trade deadline.
After acing his offseason test, Hoyer’s summer assignment is not only to improve the Cubs’ chances of making the postseason, but also to ensure they can make some noise once they get in. That could depend on whether they finish with one of the NL’s top two records, thus getting a bye and avoiding the best-of-three wild-card round in which home-field advantage is often irrelevant.
Could the Cubs become an October surprise? It’s a question that at least has merit for once.
This is still not a great team by any stretch. If there’s any 21st-century Cubs team it resembles, it’s the 2008 edition managed by Lou Piniella. On July 8, 2008, one day after the Brewers traded for Cleveland ace CC Sabathia, Cubs GM Jim Hendry acquired Oakland A’s starter Rich Harden and reliever Chad Gaudin for four prospects, including future American League MVP Josh Donaldson.
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It was a trade unlike any that Cubs fans had seen. Hendry announced the deal live on WGN-9 during a night game, and soon everyone at Wrigley Field was on their flip phones talking about the very un-Cub-like move.
Piniella’s ’08 Cubs won 97 games but were swept 3-0 by the Los Angeles Dodgers in an NL Division Series best remembered for Ted Lilly dismantling the dugout plumbing at Dodger Stadium with a bat after the Game 3 loss. Hendry’s Cubs teams never recovered, leading to his firing by Ricketts in 2011 and the start of Epstein’s rebuild.
Like the ’08 team, the 2025 Cubs skew older with a veteran-heavy clubhouse, which should help the young core of Crow-Armstrong, Miguel Amaya, Matt Shaw, Cade Horton, Daniel Palencia and Ben Brown. Ian Happ and Nico Hoerner are the only remaining links to the Joe Maddon teams.
“We definitely feel our veteran presence,” Crow-Armstrong said. “We have a lot of experience, good people around. Guys who have done this right for a long time.”
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The Cubs have shown they can win by any means necessary, which has lifted expectations at Wrigley. It’s only mid-June, but every home game reeks of a big-game atmosphere.
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Counsell’s role as a villain in Milwaukee, where even his own brother-in-law boos him, makes this rematch at Wrigley a bit spicier. Even Cubs fans have avoided the usual panic that ensues when an offense that was on automatic the first two months seems to have stalled out. The Cubs entered Monday ranked 23rd in runs (51) this month, 25th in OPS (.661) and batting average (.227) and 29th in on-base percentage (.278).
Despite that, they had managed to go 8-6 in June thanks to a 0.98 bullpen ERA and a 3.19 ERA by the Shota-less rotation. Games they would’ve blown last June are going the other way.
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With Imanaga possibly returning as soon as next week in St. Louis, the Cubs will be able to move a starter — likely Colin Rea or Brown — back to the bullpen. Brown, who has fluctuated between great and “Oh, no!” also could go to Iowa depending on his next couple of starts.
Horton has solidified his rotation spot, though the Cubs are closely monitoring his workload. His 65 1/3 combined innings in Iowa and Chicago already has surpassed his 34 1/3 innings in 2024 at Iowa and Double-A Tennessee.
“Certainly if you have a bunch of pitchers who are going to go past their career innings marks, we’re going to ask these questions, we’re going to think about it,” Counsell said. “There are no concrete answers here as to what is the best way to approach this.
“If we’re being thoughtful about it, every day of the year, that’s what we’re trying to do and use some data in their backgrounds to see if there are places you can diffuse their fatigue. … That’s where Cade is now. We’ll continue to monitor it with him, with Ben, with Matt Boyd. But right now we’re in really good spots.”
These are interesting times for Cubs fans, and summer is still a few days away.