For the Chicago Cubs, the timing of this winter’s market could hardly be worse.
They head into the offseason needing meaningful upgrades, but The Athletic’s new free-agent rankings paint a bleak picture: this is one of the weakest classes in recent memory. In fact, over the last 10 years, only one offseason had a worse crop of free agents, and that was 2017.
That year, the headliners included two future World Series champion Cubs in Dexter Fowler and Aroldis Chapman. Chicago’s major move came through the trade market, when it acquired Wade Davis from Kansas City and sent slugging outfield prospect Jorge Soler to the Royals.
The free-agent names the Cubs ultimately brought in that winter - Jon Jay, Koji Uehara, Brett Anderson and Brian Duensing - tell the story. If Jed Hoyer can’t make a serious push for this winter’s top option, Tarik Skubal, the class could end up looking similarly thin for Chicago.
Pitching is the one clear strength at the top of the market, which matters because that’s the Cubs’ biggest need. After Skubal, the list includes Freddy Peralta, Sonny Gray, Michael King, Adrian Morejon and others. On the position-player side, though, the pool is much thinner, and that leaves real questions if the Cubs were to let Ian Happ and/or Seiya Suzuki walk.
That kind of market naturally pushes the conversation back toward trades, and Hoyer has already shown a willingness to go that route. Last winter, his biggest swing was the trade for right-hander Edward Cabrera, a deal that sent top prospect Owen Caissie to the Miami Marlins. So far, it hasn’t worked out for either side.
There are still some names that could be available this winter. Mariners starters Logan Gilbert and George Kirby are among them, as is Guardians outfielder Steven Kwan. Speculation has also touched players like Ronald Acuña Jr. and Mason Miller, but that’s far from something to count on.
All of it sits under the added pressure of CBA talks and the likely lockout hanging over the offseason. However this plays out, Hoyer and the Cubs are facing a winter with very little margin for error - and one that could go a long way toward defining the club’s current contention window.
In Other News...
Cubs Could Benefit If Dodgers Finally Start Cutting Costs
The Dodgers have spent years operating like a team with no real roster ceiling, but this offseason could force a more careful look at the books. If payroll pressure and the possibility of a new salary cap start to reshape their plans, a few familiar names could surface in trade talks, and that is the sort of development front offices around the league, including the Cubs, keep a close eye on.
For Chicago, the appeal is obvious: when a star-heavy team even hints at trimming costs, useful players can become available where they were never expected to be. Teoscar Hernandez, Alex Call, Emmet Sheehan and Hyeseong Kim are among the Dodgers players mentioned as possible trade candidates, though any move would depend on health, fit and how Los Angeles wants to balance its roster. For the Cubs, it is the kind of market opportunity that can open quietly and change quickly. [Read more 🡒]
Cubs Can't Afford Another Jed Hoyer Pitching Gamble To Be The Answer
The Cubs are already staring at another winter defined by pitching uncertainty, and Dustin May has emerged as one more possible name in the mix. After spending the 2026 season with the Cardinals and Brewers, he is available as a free agent, and the appeal is easy to understand: there is still enough talent in his arm to make evaluators believe there is upside to tap into if the right environment is there.
But Chicago cannot treat him like the entire answer, not with the rotation picture looking so unsettled for 2027. Mays recent struggles make him sound more like a developmental project than a safe fix, which only works if the Cubs have already addressed the bigger-ticket items on the market. The front office can take on a reclamation arm, but only if it has first done the harder work of building a staff that does not depend on another gamble paying off. [Read more 🡒]
Kris Bryant Just Got Another Brutal Sign About His Baseball Future
Kris Bryants career arc has turned into one of the tougher cautionary tales in recent baseball memory, especially for Cubs fans who still remember the peak years when he was an MVP and a centerpiece in Chicago. After injuries and a trade to San Francisco, his path took another turn with a seven-year deal in Colorado, but health problems have continued to pile up, most notably degenerative disc disease that kept him out for the entire 2026 season.
Now the Rockies are operating as if Bryant will not be part of their roster plans moving forward, a stark sign of how far things have shifted. President Paul DePodesta said the club is making moves with Bryant unavailable, and there has been no update on any contract restructuring, leaving his baseball future hanging in the same uncertain space that has defined so much of the last few years. [Read more 🡒]