One way or another, the Chicago Cubs need to take a significant step forward in 2026. While they assembled a roster that comfortably reached the postseason in 2025 — and came just one win shy of the NLCS — even that deep of a playoff run was viewed as a pleasant surprise.

The truth is, the Cubs just didn’t have quite enough to compete with the very best in the National League. That needs to change this winter.

Kyle Tucker seems less and less likely to re-sign with Chicago as free agency approaches, which means Jed Hoyer and the front office must find another creative way to upgrade the roster.

According to Jim Bowden of The Athletic, the Cubs have been tied to eight of the top free agents on the market. All of them would make the team better — but some are far more realistic than others.

Let’s start with one player who’s just one win away from bringing a World Series title back to Canada: Toronto Blue Jays shortstop Bo Bichette.

Bichette is expected to be one of the most sought-after names on the market. He’ll have just turned 28 on Opening Day 2026, and his prime years are still ahead of him.

Outside of an odd, injury-shortened 2024, Bichette has been a model of consistency since debuting in 2019. He’s posted an OPS north of .800 and an OPS+ above 120 in every healthy season.

He led the American League in hits in both 2021 and 2022, and in 2025 he bounced back in a big way — batting .311 with 44 doubles and 94 RBIs before a left knee sprain ended his regular season in early September.

Defensively, though, he regressed. Once considered above-average at shortstop, Bichette posted -13 Outs Above Average in 2025 and a negative defensive WAR, dropping his total fWAR to 3.8.

Bowden noted that several teams view Bichette as a potential third-base option moving forward — a shift that could extend his longevity and reduce wear on his legs. Either way, the calling card is clear: a consistent, high-contact bat capable of anchoring the top of any lineup.

Spotrac projects Bichette’s market value around eight years, $186 million — roughly $23 million annually.

Bowden went slightly higher, predicting seven years, $189 million, and even compared it to the Cubs’ Dansby Swanson contract as a benchmark.

That price tag shouldn’t scare Chicago. It’s less than half of what a Kyle Tucker megadeal will cost, and there’s a real argument that this is the offseason for the Cubs to go all-in. With Tucker likely departing, a big-ticket bat should be the baseline expectation for fans.

Adding an infielder makes more sense than an outfielder for the Cubs right now. The trio of Ian Happ, Pete Crow-Armstrong, and Seiya Suzuki provides stability in the outfield, and top prospect Owen Caissie isn’t far behind.

The challenge comes on the infield dirt. Slotting Bichette at third base — as some scouts now suggest — would immediately complicate things for Matt Shaw.

Shaw finished 2025 with a breakout second half after overhauling his stance and swing during the All-Star break. He’s a solid defender with serious offensive upside, and the Cubs may hesitate to block one of their most promising young hitters.

While Shaw has experience at second and shortstop, moving him there would come at the expense of the elite up-the-middle defense anchored by Dansby Swanson and Nico Hoerner. That’s a trade-off Chicago may be reluctant to make.

This ultimately comes down to how aggressive the Cubs plan to be.

If the front office’s goal is simply to fill out a competent, balanced lineup, they might not need to spend nearly $200 million on Bichette.

But if Jed Hoyer and Craig Counsell are serious about building depth on their depth — the kind that separates good teams from great ones — Bichette becomes a fascinating piece.

Rotating him between shortstop and third base while mixing in Swanson, Hoerner, and Shaw could give Chicago a dynamic, matchup-proof infield.

He’s not a perfect fit, but he’s a proven one. If the Cubs want to make the leap from playoff contender to legitimate World Series threat, these are the kinds of players they need to consider.

Still, with Toronto likely motivated to bring him back, Chicago may find itself on the outside looking in for this one.