The Chicago Cubs enter the 2026 season intent on continuing the upward trajectory that defined their most recent campaign, a year that marked a clear return to relevance within the National League.

After several seasons of retooling and recalibration, the Cubs took a meaningful step forward in 2025, finishing with a 92–70 record and securing second place in the highly competitive National League Central.

That performance represented more than just an improved win total, as it signaled tangible progress in roster construction, player development, and organizational direction under increased expectations.

Perhaps most importantly, Chicago returned to the postseason for the first time since 2020, ending a playoff drought that had become a lingering source of frustration for the fan base.

The Cubs did not merely appear in October baseball but demonstrated an ability to compete under playoff pressure, validating their regular-season success.

In the MLB Wild Card Round, Chicago eliminated the San Diego Padres, showcasing poise, timely hitting, and disciplined pitching in a series that reinforced their growth.

That victory marked a significant milestone for a roster that blended emerging talent with experienced contributors, many of whom were tasting postseason baseball for the first time.

Chicago’s playoff run ultimately ended in the National League Division Series, where they fell to the Milwaukee Brewers in a tightly contested five-game series.

Despite the elimination, the Cubs pushed Milwaukee to the limit, underscoring the narrowing gap between themselves and the division’s most consistent contender.

That NLDS defeat, while disappointing, served as a valuable measuring stick and highlighted areas where incremental improvement could translate into deeper postseason success.

With momentum established and expectations rising, the Cubs entered the offseason focused on sustaining competitiveness rather than initiating another reset.

Chicago’s front office made several targeted moves, signaling an intent to reinforce the roster rather than overhaul it.

The most notable addition came in the form of right-handed pitcher Edward Cabrera, whose upside and raw stuff added intrigue to the Cubs’ pitching mix.

Beyond Cabrera, the Cubs also added depth pieces including Hunter Harvey, Phil Maton, Hoby Milner, and Tyler Austin.

These acquisitions addressed bullpen depth, situational flexibility, and roster insurance, reinforcing the Cubs’ emphasis on balance and durability.

While those moves provided incremental upgrades, Chicago’s broader objective remains clear: elevate the roster from playoff participant to legitimate championship contender.

Given that goal, league observers widely believe the Cubs are not finished making additions this offseason.

One area that continues to draw attention is the starting rotation, where added reliability and experience could significantly raise the team’s competitive ceiling.

That need has linked Chicago to one of the most intriguing remaining free agents on the market, a veteran pitcher with a long track record of durability.

According to a recent Sports Illustrated article by Will Laws and Nick Selbe, the Cubs have emerged as a potential landing spot for Chris Bassitt.

Bassitt was ranked No. 14 on their list of the top 15 remaining free agents, reflecting both his consistency and the limitations that accompany his age.

Laws and Selbe described Bassitt as the “metronome” of the current pitching class, a characterization rooted in his dependable workload and stable production.

Over the past four seasons, Bassitt has made at least 30 starts each year, a rarity in an era defined by workload management and frequent pitching injuries.

During that span, he has posted a combined 3.77 ERA while maintaining a strikeout rate consistently hovering around 22 percent.

Those numbers underscore Bassitt’s ability to provide quality innings without dramatic fluctuation, a valuable asset for teams with postseason aspirations.

However, Laws and Selbe also noted that Bassitt’s declining velocity and advancing age temper expectations regarding his role in high-leverage playoff situations.

Entering his age-37 season, Bassitt is no longer viewed as a frontline starter but rather as a stabilizing presence capable of anchoring the middle or back end of a rotation.

Despite that, the authors emphasized that Bassitt remains a valuable commodity, particularly for teams seeking innings coverage and regular-season dependability.

They further projected that Bassitt could still command a multi-year deal, even at this stage of his career.

Notably, Laws and Selbe predicted that the Cubs would ultimately emerge as the team to sign Bassitt this offseason.

From a roster-construction standpoint, the fit appears logical for Chicago.

The Cubs’ rotation, while improved, would benefit from the presence of a veteran starter capable of absorbing innings and reducing strain on younger arms.

Bassitt’s experience could also provide mentorship for developing pitchers, offering strategic insight and preparation routines cultivated over a lengthy MLB career.

Slotting Bassitt into the second half of the rotation would allow Chicago to maintain flexibility while preserving upside among its younger starters.

For a team aiming to solidify itself among the National League’s elite, that type of balance can be crucial over a 162-game schedule.

Adding Bassitt would not necessarily be about postseason dominance but rather ensuring the Cubs reach October with a healthy, rested pitching staff.

That reliability could prove invaluable in a division where margins between contenders are often thin.

However, Chicago is unlikely to have a clear path to signing Bassitt without competition.

Multiple teams across the league are believed to be monitoring the veteran right-hander, recognizing the value he brings even in a diminished role.

One club frequently mentioned in connection with Bassitt is the Detroit Tigers.

Detroit, like Chicago, is seeking rotational stability as it attempts to transition from rebuilding phase to sustained contention.

Bassitt’s résumé aligns well with teams looking to bridge that gap without committing to long-term risk on younger, unproven arms.

During the 2025 season with the Toronto Blue Jays, Bassitt appeared in 32 games and finished with an 11–9 record.

He posted a 3.96 ERA while striking out 166 batters, demonstrating that his effectiveness remains intact despite physical decline.

The former All-Star has recorded an ERA under 4.00 in four of his last five seasons, a consistency that continues to bolster his appeal on the open market.

While Bassitt may no longer dominate lineups, his ability to limit damage and navigate opposing orders multiple times remains a strength.

For contenders and fringe contenders alike, that skill set carries substantial value, particularly over the course of a long season.

As the offseason unfolds, Chicago’s pursuit of Bassitt will serve as a signal of how aggressive the organization intends to be.

Signing a veteran starter would reinforce the Cubs’ commitment to incremental improvement rather than relying solely on internal development.

It would also reflect confidence in the core that delivered a 92-win season and a playoff series victory in 2025.

Whether or not Bassitt ultimately lands in Chicago, the Cubs’ direction is clear.

They are no longer content with merely returning to relevance, instead seeking the final pieces required to compete consistently for deep postseason runs.

The coming weeks will determine whether that ambition translates into another significant addition, one that could help shape the trajectory of the 2026 season and beyond.