What are the Chicago Cubs doing this offseason?
The Chicago Cubs are overseen by a hands-off ownership group that defers all baseball decisions to the baseball operations department. The front office, in turn, thinks of almost everything in business terms. That deliberate, patient style is all about surplus value, return on investment and data-driven decisions. This cautious approach is not unusual in Major League Baseball, but there are times when it feels like this big-market franchise takes it to an extreme.
Advertisement
It’s way too early to start looking ahead to next year’s class of free agents, especially after all the time wasted on the idea of Shohei Ohtani starring at Wrigley Field when the Los Angeles Dodgers represented such an obvious fit. There are still two months until pitchers and catchers report to spring training in Arizona. At this rate, there should still be plenty of good players available when Cubs Convention rolls around in January, and maybe some good questions for the team’s executives about why Cody Bellinger hasn’t signed yet.
Insiders expected the Cubs to be one of the more active teams this winter, particularly since president of baseball operations Jed Hoyer shocked the baseball world by hiring Craig Counsell and firing manager David Ross. Two weeks into December, however, the Cubs haven’t added anyone from outside their organization to the 40-man roster.
Every offseason has interconnected pieces and overlapping parts, and this one has so far revolved around the Ohtani negotiations, Yoshinobu Yamamoto’s posting process, and Scott Boras clients such as Bellinger, Matt Chapman, Jung Hoo Lee, Blake Snell and Jordan Montgomery. The long-anticipated trade of Tyler Glasnow, a target of the Cubs now off to the Dodgers so the Tampa Bay Rays can shed his $25 million salary for next season, could impact other pitchers such as Dylan Cease and Shane Bieber.
“Sometimes people don’t want to go to options B and C and D until A is gone,” Hoyer said amid the Ohtani hysteria during last week’s Winter Meetings.
Hoyer isn’t interested in delivering the play-by-play account that San Francisco Giants president of baseball operations Farhan Zaidi recently gave Bay Area reporters, saying the Giants offered Ohtani the same contractual terms before he chose the Dodgers and a 10-year, $700 million deal that defers 97 percent of his salary until after the 2033 season. It doesn’t really matter how hard the Cubs, Giants or Toronto Blue Jays tried to convince Ohtani because structuring any proposal took into account his exceptional ability to create revenues and tap into a global audience. Either you sign the superstar or you don’t.

The Cubs are one of the select teams with the resources, the international network and the right urban setting to be a destination for virtually any Japanese player. That advantage plus the available track record of performance in Nippon Professional Baseball and the accumulated scouting reports usually make the Cubs more eager to pursue those players. But virtually every other big-market team had the same idea about Yamamoto, a 25-year-old pitcher with top-of-the-rotation stuff. By the middle of the Winter Meetings, it became clear that the Yamamoto discussions were advancing beyond the Cubs’ comfort zone. There has been no recent buzz about the Cubs as the Dodgers and both New York teams have lined up for Yamamoto, whose deal could exceed $300 million in total cost.
Advertisement
By this point last offseason, the Cubs had already signed Bellinger and Jameson Taillon and made progress with Dansby Swanson, who reached an agreement on a seven-year, $177 million contract by Dec. 17 last year. Some see Hoyer’s methodical movements as potentially risky. Yes, there’s a lot of time left, but there’s also a finite number of players that fit the needs of this team. Once a few players move elsewhere via trade or free agency, suddenly agents and other teams may look at the Cubs as desperate and try to leverage that feeling against them. In this scenario, Hoyer either pays more than he’d initially hoped (in terms of money or prospects) or refuses to budge, leaving his team short on impactful talent.
When it comes to the trade market, some teams believe that Cubs prospects — like those with the New York Yankees and Boston Red Sox — get pumped up publicly to an unrealistic degree. Hoyer and his staff have to be careful not to overvalue their own players and “prospect cling.” Being ultra-critical and aware of their prospects’ flaws is essential. A look at the Cubs’ top 10 prospects from a year ago shows how quickly prospect shine can fade. The counter to that would have been shipping off Christopher Morel or Javier Assad as a throw-in at the same point in time.
Others see Hoyer’s pragmatic approach and believe it could work out brilliantly. Unlike executives in San Francisco and Toronto, Hoyer isn’t desperate to land a star or trying to keep open a competitive window with players like Bo Bichette and Vladimir Guerrero Jr. There is certainly more pressure on Hoyer, especially after hiring Counsell on a five-year, $40 million contract. The finger-pointing likely shifts from Ross to Hoyer if things go sideways in 2024. But Hoyer isn’t at a point where he needs to make moves just to appease an owner or fall in line with a publicly traded company. The fan base may be restless, but until Cubs chairman Tom Ricketts gets to that point, there’s little reason for Hoyer to shift gears.
The ideal scenario for Hoyer involves being able to make some trades to bring in talent and upgrade various areas of the roster. Then, someone like Bellinger or Chapman ends up falling to the Cubs on a more palatable deal than what they’re asking for now. Rival executives believe this is a plausible scenario, particularly with Chapman, because they are looked at as very good everyday players who want to be paid like truly elite players.

Because of Bellinger’s apex — he’s a former MVP who showed he can reach a similar level of success with his 2023 performance — he may be able to pull that off. But that’s not guaranteed. While Cubs fans are undoubtedly aware of Bellinger and both the risk and the ceiling he carries, Chapman is a more unfamiliar player.
Advertisement
After a brilliant April (216 wRC+) with the Blue Jays, Chapman struggled the rest of the way (84 wRC+). While his strikeout rate did jump a bit during those final five months, his batted ball numbers gave talent evaluators optimism that he’s headed for a strong 2024 instead of a steep decline phase. He’s also a four-time Gold Glove winner, making the third baseman the kind of two-way player the Cubs value highly.
San Francisco seems more focused on pitching at this moment and Chapman is a known quantity in the Bay Area after playing for Bob Melvin and the Oakland A’s. The Yankees have their man in Juan Soto, another Boras client/upcoming free agent who said he’s going to let Boras “do his magic for me.”
The teams “desperate” to make a splash are dwindling. Hoyer needs to make other moves. Adding a veteran starter near the front of the rotation and upgrading the bullpen with multiple arms are necessary steps. Adding one hitter to help the offense won’t be enough, either. But if Hoyer plays his cards right, it’s not impossible to think the Cubs could reunite with Bellinger and make sure they don’t miss the playoffs by one game again.
“I’ve been pretty open, I don’t love the idea of long deals,” Hoyer said. “It’s hard to see into the future that well. You’re betting on human beings with bones and ligaments and all those different things. But certainly there’s times when a player’s talent (makes) it make sense to do that. So, yeah, in theory, you’d love to keep deals shorter. If you have to pay a little more per year, I think it makes sense to do that, to make your future that much more nimble. But there are times when it makes sense to (go longer).”
(Top photo of Jed Hoyer: George Walker IV / Associated Press)
ncG1vNJzZmismJqutbTLnquim16YvK57lGpqcW5ha3xzfJFsZmpqX2aCcK%2FUm6pmp5abwKat0qilZp6imrJurcaepZyxXam%2ForDErGY%3D