
During the MLB Winter Meetings in Orlando, the ping pong balls bounced the right way, and the Chicago White Sox were awarded the first overall pick in the 2026 MLB Draft.
There likely isn’t another offseason development on the horizon that will be as exciting — or as consequential — as that.
In fact, I’ve already argued it could be the most significant moment for the organization in the last 20 years. That’s how meaningful this opportunity is.
On paper, holding the top pick represents a massive advantage for a rebuilding franchise in need of elite young talent. In practice, it also introduces a familiar sense of unease for a fanbase that has watched this organization overcomplicate decisions that should be straightforward.
If you’re not at least a little nervous about the White Sox mishandling this… you probably haven’t followed the organization closely enough over the past two decades.
The first overall pick in Major League Baseball isn’t simply about identifying the best amateur player, as it often is in other sports. It’s also directly tied to bonus pool allotment. The team selecting first receives the largest pool of draft money to sign its class, which adds a strategic layer that can complicate the decision-making process.
Rather than selecting the best player available, teams sometimes opt for an under-slot pick at the top in order to redistribute money later in the draft.
That approach has become increasingly common across the league, particularly among organizations that prioritize cost control. The logic is simple: spreading resources across multiple picks can, in some cases, generate more total value than concentrating them on one elite prospect. Teams may try to float a player to the second round with a pre-negotiated deal or come away with two or three top-50 talents rather than the single best player on their board.
While that strategy can be effective in drafts with a flat or subjective talent landscape, it becomes far riskier when there is a clear consensus at the top.
Which is why the White Sox holding the first overall pick still gives me pause.
This organization has a documented history of prioritizing financial flexibility, sometimes at the expense of securing elite, top-end talent. With UCLA shortstop Roch Cholowsky emerging as the early favorite to go first overall — and widely viewed by evaluators as one of the strongest college prospects in recent memory — my concern isn’t about his ability. It’s whether the White Sox might convince themselves that another option is smarter.
Some fans and media members are already beginning to do just that, often in what feels like an attempt to sound like the smartest person in the room by being contrarian.
Chris Getz’s recent comments on 670 The Score’s "Mully and Haugh" addressed many of those concerns, even if he didn’t do so explicitly. Rather than framing the No. 1 pick as a financial puzzle or strategic maneuver, Getz spoke about it as an opportunity uniquely aligned with the talent at the top of the draft.
“The number one pick is obviously a big deal for an organization and a fanbase,” Getz said. “But the great thing is, this looks like a draft that you really want that number one pick.”
That distinction matters. He didn’t reference “a top pick.” He emphasized the number one pick as the advantage itself.
Getz acknowledged that not every draft presents a clear-cut choice at the top. In flatter draft classes, teams often feel justified prioritizing flexibility over certainty. This year, he suggested, the talent at the top changes that calculus.
“There have been plenty of drafts throughout the years where you’re focused perhaps more on suspending throughout the draft because you feel like the talent isn’t so extreme at the top,” Getz said. “But in this case, it looks like we’ve got a chance to get a player that is big-time impactful.”
That language suggests this front office understands the danger of overthinking the moment. It also reinforces the idea that the true value of the first overall pick lies in decisively using it — not maneuvering around it.
Getz’s most revealing comments came when the conversation turned to the pressure associated with being selected first overall. Asked about Cholowsky’s background — his father spent years in professional baseball and is now an MLB scout — Getz emphasized the importance of familiarity with the spotlight.
He also didn’t appear interested in getting “too cute” with the top selection.
“There is a responsibility, an honor, and a certain level of pressure that comes with being associated with 1:1,” Getz said. “It gets a lot of attention.”
“Teams that maybe try to get cute and overdraft someone to save in other places… I’ve seen players really struggle with that,” he added.
The implication is clear. Once the pick is made, bonus pool maneuvering disappears from the conversation. What remains is the expectation attached to the player — and not every prospect is equipped to carry it.
A player who understands that attention is better prepared to handle it. That context naturally favors a polished college player who has faced elite competition, scrutiny, and expectations.
Or perhaps a college shortstop with an advanced offensive approach, defensive reliability, and baseball in his blood.
A college player appears to be the clear preference. Getz spoke enthusiastically about adding someone who could move quickly through the system and join the current core in Chicago.
“The proximity,” he noted, referencing Athletics first baseman Nick Kurtz — who was drafted in 2024 and hit 36 home runs in 2025 — mattered just as much as the upside.
“Just envisioning the current group that we have… and then to add this, potentially as quickly as some of these guys have moved, it’s really encouraging,” Getz said.
That’s not language typically associated with a long-term high school development project. It reflects a desire to add a player who can move efficiently through the minors and impact the next competitive window.
Let’s call it what it is. Barring something unforeseen, Cholowsky should be the White Sox’s first overall pick next summer. Is it guaranteed? Of course not. There’s an entire college season still to be played.
But reading between the lines of Getz’s comments makes the direction fairly clear — and, frankly, it alleviates many of the long-standing fears surrounding this pick.
Without leaning into a corny pun, it’s fair to say the White Sox GM "gets it."
This is about taking the best player available. It’s about prioritizing both talent and makeup. It’s about selecting someone who can move quickly and make an impact in Chicago.
Not getting cute. Not trying to outsmart a near-universal consensus.
That’s exactly what you want to hear from a front office holding the first overall pick. This is a rare opportunity — not just to pick near the top, but to secure a potential face of the franchise.
And, for once, it appears the White Sox are prepared to take full advantage of it.