The vibes are generally positive around the Chicago Cubs right now, coming off a strong close to the offseason that saw the team land Alex Bregman in free agency and trade for a dynamic young righty in Edward Cabrera. But make no mistake: In this market, with this fan base, you're never very far away from DEFCON 1 — and this year more than most is shaping up to be make-or-break.
That was already the case given how the first two years of the Craig Counsell era have played out, with 83 wins in 2024 and an NLDS exit last season followed by the departure of Kyle Tucker in free agency. With Counsell now entering year three and a roster overflowing with the talent, it's past time for a breakthrough — expectations that were only reinforced by owner Tom Ricketts during his first media appearance of the spring.
Cubs owner Tom Ricketts: “We want to win the division. We should win the division. We should be right there. You want to win the division for a lot of reasons not just because its aggravating not to – but you want to put yourself in the best position for the playoffs as well.”
— Jesse Rogers (@JesseRogersESPN) February 16, 2026
Ricketts isn't often confused for a firebrand, which makes his choice of words here particularly stark. Chicago hasn't won its division in a full (i.e., non-COVID) season since 2017, which is also coincidentally the last time they reached the NLCS. Ricketts has given his front office more than enough time to transition out of the old World Series core into something new; it's time for that something new to start bearing fruit.
Granted, this is hardly vintage George Steinbrenner. But it still qualifies as an eye-opening public statement from someone not prone to giving them very often. And it should have several key Cubs players on high alert.
3B Alex Bregman
Pressure is nothing new for Bregman, who's spent pretty much the entirety of his MLB career to date competing at the highest levels of the sport. And while he had to settle for a short-term contract last offseason, he was finally able to cash in this time around, securing five years and $175 million from Chicago — with no opt-outs or options in sight. On the surface, he would seem pretty secure right now.
But when the Cubs handed him that deal — and opted against putting that money toward an effort to re-sign his former teammate, Kyle Tucker — they made him the new de facto face of the franchise. Chicago has plenty of big bats around him, but Bregman is the man, the emotional leader and the one expected to come through when the chips are down. If the Cubs regress in 2026, it's going to ding his reputation a bit as a result; and as he enters his age-32 season, who knows how many more bites at the apple he'll have?
OF Pete Crow-Armstrong
Over the first half of the 2025 season, PCA was the toast of the town, a legitimate MVP candidate thanks to his elite defense in center and his red-hot bat. But the latter came undone down the stretch amid a hail of strikeouts and poor plate discipline, old issues rearing their ugly heads at the worst possible time. Which now begs the question: Which Crow-Armstrong is the real Crow-Armstrong?
The answer will have major ramifications not just on the Cubs' fortunes this season but on PCA's wallet. He's already reportedly turned down one extension, and if he realizes his potential this year, Chicago will be desperate to pay him before he hits arbitration in 2027. If he stumbles again, though, this Cubs team's ceiling shrinks considerably, and the questions about Crow-Armstrong's ultimate future will only get louder.
LHP Shota Imanaga
The Cubs sent Imanaga something of a message this winter, turning down a three-year, $57.75 million team option that would have locked the lefty up through 2028. On the heels of a nightmarish close to 2025, it felt like a warning: Prove to us that you can be a frontline MLB starter long term, or else.
It's not an unfair question. Imanaga has been largely good over his two MLB seasons, but home run problems came back to haunt him in a major way last year, and he's now 32 with declining velocity on a fastball that was never particularly fast to begin with. He's now on a one-year deal; if he bounces back, he'll be in for a major payday next winter. He also might be the single biggest pivot point for this Cubs season: Even with Edward Cabrera in the fold, Chicago's rotation remains a question mark, and Imanaga looking more 2024 than 2025 elevates this team's ceiling considerably.
OF Seiya Suzuki
Like Imanaga, Suzuki is also slated to be a free agent at the end of the season. And despite how good he's been as a hitter so far in his MLB career (career OPS+: 129), his market is a tough one to peg right now. He's an incredibly well-balanced hitter, but he's also right-handed on the wrong side of 30 without a clear defensive home — typically a tricky demographic on the open market.
Suzuki can quiet those doubters in a major way by delivering another elite offensive season. And while Bregman gets the headlines and PCA has captured Chicago's heart, it's Suzuki he might be the team's most important hitter: With Tucker gone, no one else has the ceiling at the plate that he does, and he needs to be a force in the middle of the order for this team to get where it wants to go. If he's merely good rather than great, the Cubs are in trouble.
2B Nico Hoerner
Hey look: Yet another Cub entering a contract year. Hoerner has been a rock in Chicago's infield for years now, but he's approaching 30, with a game predicated on speed, base-running and defense — skills that may or may not age gracefully when projected over the life of a new, long-term contract.
Hoerner means more to the Cubs than he does to any other team in the league. But Chicago also has a youngster in Matt Shaw breathing down his neck, plus more Minor League depth behind. It would be all too easy for the Cubs to move on in the winter if Hoerner has a subpar season. That would also be devastating to the team's World Series hopes this year, considering how crucial he is as a two-way player.
OF Ian Happ
It feels like Happ is always the one to take the fall when things aren't going well with the Cubs. It's understandable: He's the team's longest-tenured player at this point, the lone remaining link to the Bryant-Rizzo-Baez glory days, and he's the sort of player it can be easy to take for granted — good but rarely great all the way around, and prone to hot and cold streaks.
Like so many players on this list, Happ is set to test free agency for the first time next winter. He's also set to turn 32 in August. Can he play well enough to earn one more long-term deal? And more pressingly, can he play well enough to hold off the players behind him in a crowded outfield depth chart? His status as an everyday player can no longer be taken for granted, not with the stakes this high and so much talent around him.