Winter Meetings preview: Cubs seem to understand it’s time to make splash again

The Chicago Cubs are targeting a higher level of the free-agent market and signaling an openness to spending for certain players, according to team and league sources briefed on the club’s deliberations.

Reading that sentence, Cubs fans may understandably roll their eyes.

After all, this is a multibillion-dollar franchise with generations of loyal customers, a valuable multimedia portfolio and an iconic ballpark that anchors the surrounding real-estate empire. A big-market team that wins 92 games and a playoff round is supposed to keep going for the World Series.

The usual caveats apply here. The Cubs are not changing their business/baseball model to the point where their payroll will approximate what the Los Angeles Dodgers, New York Yankees or New York Mets spend on talent.

Jed Hoyer’s front office still has to acquire the right players who can perform at Wrigley Field. Organizations don’t raise banners for trying.

But by entering the Dylan Cease negotiations — before the pitcher agreed to a seven-year, $210 million contract with the Toronto Blue Jays — the Cubs showed a willingness to pursue a potential top-of-the-rotation starter rather than default to a safer investment or wait to see if prices drop.

The Cubs have also reengaged with All-Star third baseman Alex Bregman and demonstrated that their bullpen won’t be entirely remade with relievers on one-year contracts and minor-league deals with invitations to spring training.

As the industry gathers in Orlando, Fla., this week for Major League Baseball’s Winter Meetings, the Cubs should be a team to watch.

“It will be an active offseason,” Hoyer said. “We’ll be really active in the pitching market.”

Winter Meetings preview: Cubs seem to understand it’s time to make splash again

Michael King made just 15 starts in 2025 after finishing seventh in the NL Cy Young Award voting the previous season. (Orlando Ramirez / Getty Images)

While the Cubs have not yet put the full-court press on Michael King, their interest is real. As teams such as the Blue Jays and Boston Red Sox fill out their rotations, the Cubs could be playing it coy, hoping they have fewer suitors to bid against.

King’s career arc has unfolded in a way that made the Cubs take notice. Educated at Boston College, he got drafted by the Miami Marlins in 2016 and then traded to the Yankees, a first-class organization that the Cubs have repeatedly tried to mine for talent and ideas, through trades for pitching and hiring for staff positions.

Demonstrating his aptitude and self-assurance, King developed into a trusted member of the Yankee Stadium bullpen and lobbied to become a starting pitcher. His instincts proved to be correct.

King’s upside turned him into a key piece of New York’s blockbuster Juan Soto trade. In his first season with the San Diego Padres — and only full year in a major-league rotation — King finished seventh in the 2024 National League Cy Young Award voting.

That momentum slowed down due to various injuries (right shoulder inflammation, left knee inflammation) that limited King to 15 starts this year. During their playoff series at Wrigley Field, the Padres used him out of the bullpen for one inning in the elimination game they lost.

Heading into his age-31 season — and coming off an injury-plagued year — it’s unlikely King will get an extremely long deal or an exorbitant guarantee. That’s also part of what makes him so appealing.

The Cubs believe they could formulate a plan that would help King stay healthy and reach that tantalizing ceiling on a more consistent basis.

For a free agent in this upper-middle class, Hoyer’s front office has a reliable template, which includes good security for multiple years, a high annual salary and a robust overall number — without going to the top of the market.

At the same time, the Cubs are also expected to be involved in the process as Tatsuya Imai evaluates his options and maps out the next stage of his life. He’s not necessarily determined to relocate to the West Coast, nor is he averse to playing in New York or Philadelphia. At the age of 27, he’s open-minded and ready to make the leap.

A dazzling playoff performance by Yoshinobu Yamamoto — a similarly sized right-handed pitcher listed at 5-foot-10, 176 pounds — likely increased Imai’s leverage. Perhaps interest from multiple big-market franchises will spark a bidding war that escalates to a point that makes the Cubs uncomfortable.

But the Dodgers can’t sign every good player out of Asia. And the Cubs have established a presence and built up credibility within Nippon Professional Baseball.

Even if having a Japanese teammate doesn’t really matter to Imai, the Cubs have learned a lot from their experiences with Shota Imanaga and Seiya Suzuki, and the club can tailor its recruiting pitch accordingly.

“We’ve proven that we’re a place where Japanese players can succeed,” Hoyer said. “A lot of teams don’t have any kind of infrastructure to deal with that, so when you’re talking about the market for Japanese players or Korean players, it’s not 30 teams that are in theory going after those players. Because a lot of teams just don’t have the infrastructure set up, so I do think we have that advantage.”

Imai’s success should enable him to cash in this winter. After three straight seasons with an ERA hovering around 2.30, Imai delivered his best season yet with a 1.92 ERA, a 27.8 percent strikeout rate and a 7.0 percent walk rate. The results are undeniable.

The questions — especially if the price tag goes higher — revolve around how the stuff translates when facing major league hitters. Is the breaking ball sharp enough? Does his fastball — which sits in the mid-90s and touches higher — have the type of characteristics teams seek?

Coaches and club officials often feel like they can unlock more with pitchers once they get a chance to work with them. At this point, it’s unclear whether the Cubs view Imai as a likely ace or more of a mid-rotation piece. That final evaluation will determine their level of aggressiveness.

It’s also worth remembering that the Cubs currently have only Gold Glove shortstop Dansby Swanson and reliever Phil Maton under contract after the 2026 season, when baseball’s collective bargaining agreement is set to expire.

Exciting young players such as Pete Crow-Armstrong and Cade Horton remain under club control through 2030. But this offseason represents an opportunity to plan for the future and follow through on the promises to build a consistent contender.

“We’re not going to be bound to much going into ‘27, ‘28, ‘29,” Cubs general manager Carter Hawkins said. “Whether or not there’s a new economic structure is well, well beyond my pay grade. But, yes, there are going to be a lot of alternatives at that point.

“It’s both exhilarating to think about and also a little scary to try to figure out. But we’re confident in our ability to find wins — and find wins for a cost that makes sense for us. We’ll try to continue to do that in all the different markets.”

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