With the 2026 MLB Draft compressed into two days, the Cubs’ recent draft patterns offer clues

The 2026 MLB Draft begins Saturday at noon Chicago time, and the format will look different. Instead of stretching the early rounds across three days, the league will complete rounds 1 through 4 on Saturday and then finish rounds 5 through 20 on Sunday, effectively compressing the usual draft window into two days. For the Chicago Cubs, that means the time between their first-round pick and the start of their deeper inventory-building is shorter than it has been recently.

The question for fans is what Chicago’s player-identification preferences will translate into at No. 23. One way to frame the decision is to look at the last five Cubs drafts conducted by current scouting director Dan Kantrovitz, since those classes can show what the organization values when the talent board falls a certain way. Across those five first-round selections, the common throughline is a preference for college players: all five of Kantrovitz’s first-round picks came from four-year programs, according to the Yahoo Sports review.

That college bias has not meant the Cubs avoid high-ceiling swings entirely. The same look back describes how Kantrovitz has been more willing to take high school players after the first round, and it also points to the Cubs being prepared to pay an over-slot bonus to sign some of the prospects they like. In other words, the organization’s approach is not “safe by default,” but rather “college first when selecting from the most constrained part of the board.”

The retrospective also highlights a second tendency: the Cubs have shown a willingness to choose higher-upside prospects who fall due to health concerns. The Yahoo Sports piece distinguishes earlier, comparatively lower-risk profiles from later bets, including references to pitcher selections tied to limited recent workload or recovery timelines. It cites the Cubs taking Cade Horton in a bold context after Tommy John surgery, and it also describes Ethan Conrad as another player whose availability may have been shaped by health questions.

At the same time, the Cubs’ draft profiles are not purely pitcher-leaning or purely hitter-leaning. The review says the Kantrovitz era generally has been more favorable to hitters than pitchers, with one notable exception described as the “wacky 2022 draft,” reinforcing that the organization’s approach can shift when the talent at their pick changes. That flexibility matters in a draft year where the top of the board can behave differently depending on which prospects are actually healthy, signable, and present at each slot.

Finally, the Cubs have continued to land a mix of “raw talent” from high school even when those players are not first-round targets. The review lists several names tied to high school upside the Cubs took a chance on outside of the first round, including James Triantos, Drew Gray, Jackson Ferris, Nazier Mulé, Zyhir Hope, Kaleb Wing, and Josiah Hartshorn. Those additions provide a picture of how Chicago plans to build its future: using the early round to set a foundation (often via college) while later selections absorb more projection and variance.

The immediate takeaway for Saturday’s No. 23 decision is not a prediction of a specific player, but a set of probabilities. If the Cubs follow their most recent first-round tendencies, they will likely be looking at college options first and treating the first selection as a signing-and-development bet that can be supported by a college track record. At the same time, the historical record of health-driven falls suggests that Chicago is willing to lean into upside if the board forces their hand and the risk feels manageable. What to watch next is whether the Cubs keep the pattern on Saturday, then how they distribute their risk across rounds 5 through 20 on Sunday as the talent board widens.

If you’re evaluating the draft strategy from the outside, it is also worth remembering that draft-day needs, prospect availability, and signing leverage can change quickly. A team can like a type of player and still choose a different archetype at the right slot if the best remaining option is not the “preferred” one. Still, the last-five-drafts snapshot gives a useful baseline for what Chicago’s scouting leadership has tended to reward, and it sets context for how the Cubs might balance college safety with upside later in the weekend.