Rebuilds are rarely linear. For the Chicago White Sox, the past several seasons have felt disjointed — flashes of promise buried under losing records, roster turnover, and unanswered questions about organizational direction. But heading into 2026, something feels different. Not finished. Not complete. But finally structured.
This version of the White Sox isn’t chasing shortcuts or unrealistic expectations. Instead, it’s approaching a pivotal phase of the rebuild — one where development, roster clarity, and internal growth begin to translate into measurable on-field progress. The question isn’t whether Chicago will contend in 2026. The real question is whether this season marks the moment the rebuild starts pointing clearly toward contention.
To answer that, you have to look at three interconnected factors: realistic performance benchmarks, the arrival of the next prospect wave, and whether the organization can finally turn talent into consistency.
Setting the Right Bar: Why 70 Wins Matters More Than It Sounds
At first glance, setting a goal of around 70 wins might feel uninspiring. For a fan base starving for relevance, modest benchmarks can sound like settling. But context matters.
The White Sox finished 2025 at 60–102, a season defined by growing pains, roster experimentation, and a young core learning how unforgiving Major League Baseball can be. A 10-win improvement would represent more than just incremental progress — it would signal real organizational growth.
Historically, teams coming out of deep rebuilds often make this exact type of jump before taking a larger leap. Those additional wins usually come not from star acquisitions, but from better fundamentals: improved bullpen management, fewer defensive miscues, smarter situational hitting, and a roster that understands how to close out tight games.
That last part is especially critical. In 2025, the White Sox were 15–36 in one-run games. That’s not just bad luck — it’s inexperience, inconsistent execution, and a bullpen still finding its identity. Even a moderate correction toward league average in close games could swing five to eight wins on its own.
This is where 2026 becomes important. A team that can win ugly games is a team that’s learning how to win at all.
The Prospect Foundation Is No Longer Theoretical
The biggest difference between this rebuild and past attempts is proximity. The White Sox no longer have to sell fans on players who are three years away. The next wave is knocking on the door — and several of these prospects project not just as contributors, but as foundational pieces.
Braden Montgomery: A Middle-of-the-Order Blueprint
Braden Montgomery isn’t just another outfield prospect — he profiles as the type of bat this organization has been missing. A switch-hitter with power to all fields, Montgomery’s offensive profile fits perfectly in Guaranteed Rate Field. His ability to impact the baseball without sacrificing plate discipline gives him a legitimate chance to become a middle-order fixture rather than a complementary piece.
What makes Montgomery particularly important is timing. His development aligns with the maturation of the current core, meaning he won’t be asked to carry the lineup immediately — just to deepen it. That’s how sustainable lineups are built.
Noah Schultz and Hagen Smith: Changing the Rotation’s Ceiling
Pitching development has quietly become one of the White Sox’s most important storylines. Noah Schultz and Hagen Smith represent two very different but equally intriguing paths toward rotation stability.
Schultz’s size, extension, and left-handed dominance give him frontline upside if command continues to progress. Smith, meanwhile, brings a more polished strikeout profile that could translate quickly at the Major League level.
The key here isn’t whether either becomes an ace in 2026 — it’s whether the White Sox can finally supplement their rotation internally rather than relying on short-term veteran fixes. If even one of these arms establishes himself, the ripple effect on workload management and bullpen usage could be enormous.
The First Wave Matters Just As Much As The Next
While attention naturally gravitates toward new arrivals, the success of the rebuild hinges on players who already debuted in 2025. Colson Montgomery, Kyle Teel, Edgar Quero, Chase Meidroth, and Shane Smith are no longer prospects — they are young Major Leaguers entering critical developmental seasons.
Colson Montgomery: A Cornerstone in Progress
Montgomery’s rookie season offered exactly what rebuilding teams want: flashes of impact paired with obvious areas for growth. His power translated immediately, but consistency against elite pitching remains the next step. If Montgomery can stabilize his strikeout rate while maintaining power production, he becomes a legitimate long-term building block rather than just another promising bat.
Kyle Teel and Edgar Quero: Redefining the Catching Position
For years, the White Sox have treated catcher as a defensive necessity rather than an offensive asset. That could change quickly. Teel’s athleticism and leadership, combined with Quero’s bat-to-ball skills, give Chicago flexibility and upside behind the plate. Even league-average offensive production from the catching position would represent a massive upgrade.
Offensive Identity: From Passive to Purposeful
One of the most telling signs of a rebuilding team is an undefined offensive identity. In recent seasons, the White Sox often fell into long scoring droughts, lacked situational awareness, and failed to apply consistent pressure on opposing pitchers.
That has to change.
Power production will be a focal point. Reaching the 190-home-run range isn’t about chasing numbers — it’s about forcing pitchers to respect the lineup from top to bottom. The presence of Montgomery, a full season of Colson Montgomery, and potential bounce-back years from veterans like Andrew Benintendi and Luis Robert Jr. could push the offense toward league relevance.
But power alone won’t fix everything. The next step is situational maturity: advancing runners, capitalizing on mistakes, and shortening swings in high-leverage spots. These aren’t traits taught overnight — they develop as young players accumulate real MLB experience.
Bullpen Stability and Late-Game Growth
No rebuilding team wins consistently without bullpen reliability. The White Sox don’t need an elite relief corps in 2026 — they need predictability. Defined roles, fewer walks, and trust in late-inning arms can change the complexion of an entire season.
Even marginal improvement here could dramatically impact close-game results. Turning five one-run losses into wins doesn’t require perfection — it requires execution.
Why 2026 Is a Pivot Point, Not a Destination
This season isn’t about playoff odds or division races. It’s about confirmation. Confirmation that the player development pipeline is working. Confirmation that young players can adjust at the Major League level. Confirmation that the organization finally has a coherent direction.
If the White Sox reach 70-plus wins, integrate their next prospect wave successfully, and show tangible improvement in situational baseball, then 2026 becomes the bridge year — the one that makes future contention believable rather than speculative.
That’s how rebuilds succeed. Quietly. Incrementally. With patience that finally feels justified.
And for the first time in a while, the White Sox look like a team that understands exactly where it’s going — even if it’s not there yet.
