The Chicago Cubs are continuing their methodical push to strengthen organizational depth in the outfield as preparations quietly intensify for the 2026 Major League Baseball season.

With several roster changes reshaping the team’s long-term outlook, the front office has turned its attention toward reinforcing flexibility, competition, and insurance at a position group that was thinned significantly over the winter.

The departures of Kyle Tucker and Owen Caissie during the offseason created a noticeable gap in Chicago’s outfield depth chart, forcing the Cubs to re-evaluate how they want to structure the final spots on their roster moving forward.

While the core of the outfield remains largely intact, the absence of Tucker’s impact bat and Caissie’s developmental upside has left the organization searching for a reliable fourth outfielder who can contribute in multiple roles.

Rather than relying on a single acquisition, the Cubs have chosen a layered approach, adding multiple veterans and depth pieces to create internal competition and protect against injuries over the course of a long season.

That process began earlier this month when Chicago claimed Justin Dean off waivers after the San Francisco Giants designated the outfielder for assignment, a low-risk move designed to improve defensive versatility.

Dean, now 29 years old, spent much of the previous season in a limited role with the Los Angeles Dodgers, primarily serving as a defensive replacement during their World Series championship run.

Although his offensive production has been modest, Dean’s speed, glove, and familiarity with high-pressure environments made him an appealing depth option for a Cubs team prioritizing roster balance.

Shortly after the Dean acquisition, the Cubs added another name to the outfield mix by signing Chas McCormick to a Minor League contract, signaling continued emphasis on upside and bounce-back potential.

McCormick’s recent seasons have been derailed by injuries, limiting his availability and consistency, but his track record suggests far more impact than his recent stat lines indicate.

Just three years ago, McCormick posted a 3.4 WAR season with the Houston Astros in 2023, emerging as a productive everyday contributor on a playoff-caliber roster.

That performance remains fresh enough in the minds of evaluators to justify a low-cost flyer, especially for a Cubs organization that values versatility and experience in its bench construction.

Even with those two additions, however, Chicago appears far from finished in its search for outfield depth, continuing to explore additional options as Spring Training activity ramps up.

According to reporting from Greg Zumach, the Cubs are expected to sign Dylan Carlson to a Minor League deal that includes an invitation to Major League Spring Training.

While the organization has not yet officially confirmed the agreement, circumstantial evidence strongly supports the report, particularly after Carlson was spotted at the Cubs’ Spring Training complex in Arizona.

Photographs captured by Ray R. Rardin II showed Carlson participating in early camp activities, playing catch and taking part in outfield drills alongside other Cubs players.

The images quickly fueled speculation that a deal was imminent, and if finalized, Carlson would become the third outfielder added by Chicago in roughly a two-week span.

The steady stream of acquisitions underscores the Cubs’ clear objective of creating a competitive environment for the final bench spot while simultaneously bolstering Triple-A depth.

For Carlson, the opportunity represents a potential career reset after several difficult seasons that have stalled the once-promising trajectory of his professional development.

Now 27 years old, Carlson was previously regarded as one of the St. Louis Cardinals’ top prospects, praised for his switch-hitting ability, plate discipline, and defensive versatility.

Early in his career, Carlson showed signs that those evaluations were well-founded, particularly during his strong 2021 campaign at the Major League level.

That season, Carlson appeared in 149 games, posting a .266 batting average while hitting 18 home runs, driving in 65 runs, and collecting 31 doubles and four triples.

His combination of gap power and steady defense made him a fixture in the Cardinals’ lineup and a player many believed would anchor their outfield for years to come.

Carlson followed that performance with a solid, if less explosive, 2022 season, batting .236 with eight home runs, 30 doubles, four triples, and 42 RBIs across 128 games.

While the raw numbers dipped slightly, Carlson remained a valuable contributor and still appeared positioned to develop further as he entered his mid-twenties.

Unfortunately, the subsequent seasons proved far more challenging, as injuries, inconsistency, and diminishing confidence began to erode his on-field production.

Over the past three years, Carlson has struggled to rediscover his earlier form, ultimately posting negative WAR totals in back-to-back seasons.

Last year with the Baltimore Orioles, Carlson managed just a .203 batting average while hitting six home runs, reinforcing concerns about his offensive ceiling.

Those struggles dramatically shifted how teams around the league view Carlson, transforming him from a former cornerstone prospect into a reclamation project seeking stability.

For the Cubs, however, that shift also creates an opportunity to extract value without significant financial or roster risk.

Chicago’s Minor League deal would allow Carlson to compete openly during Spring Training, where performance and versatility will likely determine his immediate future.

If Carlson can demonstrate improved plate discipline, consistent contact, and defensive reliability, he could realistically earn the final bench spot on the Opening Day roster.

The Cubs have shown a willingness in recent seasons to reward strong Spring Training performances, particularly when roster flexibility and depth are at stake.

Should Carlson fall short of making the Major League roster, his presence would still serve a valuable purpose within the organization’s Triple-A system.

Depth at the minor league level has become increasingly important as teams navigate injuries, doubleheaders, and extended travel schedules throughout the season.

Carlson’s Major League experience, even during down years, would provide immediate insurance should the Cubs need to call upon an outfielder during the season.

From a broader organizational perspective, Chicago’s recent moves reflect a front office committed to incremental improvement rather than headline-grabbing acquisitions.

By targeting undervalued veterans and former high-upside players, the Cubs are attempting to maximize internal competition while preserving financial flexibility.

This strategy also aligns with the team’s long-term vision of blending homegrown talent with experienced contributors capable of stepping into defined roles.

As the 2026 season approaches, the Cubs appear intent on leaving no roster spot uncontested, particularly in areas where injuries or regression could quickly expose weaknesses.

The fourth outfielder role, while often overlooked, frequently plays a critical part over the course of a full season, contributing defensively, offensively, and situationally.

Whether that role ultimately belongs to Dean, McCormick, Carlson, or another late addition will be determined over the coming weeks of Spring Training competition.

What is clear, however, is that the Cubs are approaching the challenge with depth, patience, and an eye toward long-term stability rather than short-term fixes.

As camp progresses, all eyes will be on how these veteran outfielders respond to the opportunity, knowing that one strong spring could reshape their careers and Chicago’s roster plans.