Fantasy baseball league winners do not always come from Round 1. Sometimes they come from the boring pocket of a draft, where the market bakes in last year’s disappointment and misses what is about to change.
That is the common thread tying together this group. Zebby Matthews, Andrew Vaughn, Emmet Sheehan, and Jac Caglianone all come with very different profiles, but each offers a path to beating ADP in a meaningful way. Some need a cleaner runway. Some need better health luck. Some just need fantasy managers to stop anchoring to an ugly first impression.
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Fantasy Baseball | 4 League Winners You Need to Draft (2026)
If you are trying to find difference-makers instead of just filling roster spots, these are the names to circle.
Zebby Matthews is the classic post-hype pitcher fantasy managers forget too quickly. His first big league run in 2025 was rough on the surface, but the underlying profile still points to a starter worth betting on. FanGraphs’ 2026 projections and recent fantasy analysis continue to view him as a viable Minnesota rotation piece, and the Twins still have enough uncertainty behind their top arms for Matthews to matter early.
The appeal is straightforward. Matthews misses bats, limits walks better than most young pitchers, and has the kind of minor league strikeout history that usually earns a second chance. This is the kind of arm that gets discounted because fantasy players remember the ERA and forget the skill set.
In redraft leagues, that discount is exactly the point. You are not paying for a finished product. You are paying for strikeout upside and a realistic chance that Minnesota lets him settle into a real role. If the command stabilizes, he has the tools to return mid-rotation value at a bench price.
Andrew Vaughn might be the cleanest value play of the bunch.
The full-season line from 2025 looks ordinary, but that undersells what happened after he landed in Milwaukee. Vaughn finished last year slashing .308/.375/.493 over 64 games with the Brewers, and he has carried that momentum into spring, where he opened 2026 hitting .400 with two homers in 30 at-bats. Milwaukee’s projected depth chart also places him in a clear starting role, which matters for a player whose biggest fantasy edge could simply be stable lineup context.
This is the kind of first baseman who gets overlooked because he is not flashy. He probably is not hitting 40 homers. But 25 to 30 with a playable batting average in a good lineup is very much on the table, especially if the Milwaukee version of Vaughn is the real one.
That makes him a strong roster construction target. You can wait at first base, fill scarcer positions earlier, and still walk away with a bat that has a real chance to finish well above cost.
Emmet Sheehan is one of the more interesting upside arms in this draft pool because the Dodgers have already shown they trust him.
His MLB and minor league numbers from 2025 tell the story. Sheehan struck out 89 hitters in 73.1 big league innings for Los Angeles, while his minor league work was even more dominant. Projection systems for 2026 generally land around a mid-3s to low-4s ERA with well above-average strikeout rates, which is exactly the kind of profile that can make a leap if the workload cooperates.
The obvious risk is role management. The Dodgers always have options, and no starter on that staff feels like a lock for 180 innings. But that cuts both ways. On a team with constant health and workload questions, Sheehan has multiple paths to value. He can start, he can absorb innings, and he can pile up strikeouts on a club that should hand him plenty of win equity.
That combination is hard to find in his draft range. Even if the volume falls short of a true workhorse season, the per-inning production can still make him a major profit arm.
Jac Caglianone is the upside swing.
His first look in the majors last year did not go well, but the underlying quality of contact was better than the batting average suggested. Statcast credited him with a 12.2 percent barrel rate and a .321 expected wOBA in 2025, both signs that the raw damage was more real than the results. Before that call-up, he obliterated Double-A and Triple-A pitching after debuting on June 3, 2025, establishing himself as one of the game’s fastest-rising power bats.
That is why the fantasy case still works. The power is not theoretical. It is already here. What matters now is approach. If Caglianone trims the chase and gets to even adequate major league swing decisions, the home run upside becomes too loud to ignore.
This is not the safe pick. It is the pick you make because 30-homer upside in the middle rounds can change a season. If the adjustment comes quickly, he will not stay affordable for long.
Fantasy Baseball Takeaways
- Zebby Matthews is a skills-over-results pitching target with strikeout upside and a believable path to steady starts.
- Andrew Vaughn looks like a post-hype hitter who benefited from a new environment and now has stable playing time in Milwaukee.
- Emmet Sheehan offers strikeouts, team context, and enough role flexibility to beat his draft cost even without ace-level volume.
- Jac Caglianone is the ceiling play. If the approach improves, the power can carry him into league-winning territory.
- The common edge here is price. All four are being drafted below their realistic upside.
- In 2026, the fantasy managers who win drafts are often the ones who bet on growth instead of last year’s stat line.
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