The first week of the MLB offseason is always a bit like setting the chessboard-teams make their early moves, players make decisions on options, and the market starts to take shape. For the Chicago Cubs, this part of the winter is less about splashy headlines and more about identifying opportunities. And with a few notable names hitting free agency after declining their 2026 options, the Cubs front office-led by Jed Hoyer-suddenly has a wider pool to work with as they look to fine-tune a roster that’s close, but not quite there yet.
Let’s break down four newly available players who could be on the Cubs’ radar-and why each one brings something intriguing to the table.
Lucas Giolito – RHP, formerly Boston Red Sox
Lucas Giolito is back on the market after declining his end of a 2026 mutual option with the Red Sox. Cubs fans will recognize the name-he was a longtime fixture on the South Side with the White Sox and has been loosely linked to the North Siders in the past, including at the most recent trade deadline.
Giolito posted a 3.41 ERA over 26 starts last season, showing he still has the stuff to anchor a rotation or slot in as a reliable No. 2 or 3. He’s not the flashiest name in this year’s pitching class, but he fits the mold of the kind of arm the Cubs tend to target: experienced, durable, and capable of eating innings with above-average results. If the price is right, this could be a smart, low-drama addition to a staff that needs more depth behind its top arms.
Brandon Woodruff – RHP, formerly Milwaukee Brewers
This one’s a little more complicated, but potentially more impactful. Brandon Woodruff declined his mutual option with the Brewers after making just 12 starts last season, a year removed from shoulder surgery that cost him all of 2024. When healthy, though, Woodruff has been one of the most effective starters in the National League-power stuff, postseason experience, and a bulldog mentality on the mound.
What makes Woodruff especially interesting for the Cubs is the Craig Counsell connection. The former Brewers manager now calling the shots at Wrigley has seen firsthand what Woodruff can do. And with the Cubs in the market for high-upside pitching, this reunion could make a lot of sense-especially if Woodruff is open to a shorter-term, prove-it deal while he reestablishes his value.
Pete Alonso – 1B/DH, formerly New York Mets
Pete Alonso has been linked to the Cubs so many times over the past two seasons, it’s almost become a running joke. But now that he’s officially opted out of his deal with the Mets, the speculation has some real legs again.
The twist? Michael Busch has emerged as one of the top first basemen in the National League, which complicates things a bit.
Still, if the Cubs are looking to add a true power bat to the middle of the order-and specifically a designated hitter-Alonso checks every box. He’s a proven slugger with multiple 40-homer seasons under his belt, and his presence in the lineup would provide instant thump.
It’s not the most urgent need, but it’s the kind of move that could elevate the offense from good to dangerous.
Alex Bregman – INF, formerly Boston Red Sox
Alex Bregman opting out of his deal with Boston opens another intriguing door for the Cubs. If the front office is serious about upgrading the offense-especially with the possibility of replacing the kind of impact Kyle Tucker brought-Bregman is one of the most straightforward ways to do it.
He’s a proven performer, a postseason-tested bat with positional versatility and a high baseball IQ. Whether the Cubs would see him as a third baseman, a short-term solution at another infield spot, or simply a veteran presence who can lengthen the lineup, Bregman fits the profile of a player who raises the floor and the ceiling. His name will be connected to a lot of teams this winter, but don’t be surprised if the Cubs are one of them.
What This Means for the Cubs
This isn’t a rebuild. This is a team that’s trying to take the next step-from competitive to contending. And while none of these names guarantee a division title or a deep October run, they each represent the kind of calculated, high-upside move the Cubs have shown a willingness to explore in recent offseasons.
With more talent hitting the open market this week, the front office has more flexibility, more leverage, and more ways to get creative. Whether that means bolstering the rotation, adding a power bat, or simply creating competition in camp, the Cubs now have four more reasons to stay aggressive.
The chessboard is set. Let’s see how they play it.
