Sport: MLB

Every fantasy manager wants to look like a genius drafting elite fantasy producers late in the draft. This scenario is easier said than done with all the research tools available nowadays, but it’s a sweet feeling when you pull off finding great value deep in fantasy drafts.

In this article, I take a look at the fantasy baseball shortstop sleepers that I feel are being drafted too late. Take advantage of the high-risk, high-reward players listed below to boost your chances of reaching your league championship.

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Shortstop Sleepers for 2026 Fantasy Baseball
Jacob Wilson – SS, Athletics (ADP: 165)

Jacob Wilson displayed elite contact skills during his rookie season last year. During which he posted a .317 BABIP and finished tied for second in the AL batting title, behind Aaron Judge, with a .311 batting average.

His 13 home runs, 63 runs, and 63 RBIs also helped him finish second behind teammate Nick Kurtz for the Rookie of the Year Award. The plate vision he showcased was also outstanding, with a strikeout percentage of only 7.5, the second-lowest among qualified batters. This skill helped him go 55 straight plate appearances without a strikeout.

Wilson will be highly motivated to repeat his success after signing a seven-year, $70 million contract during the offseason. However, he is ranked 16th among shortstops in our Fantrax consensus ratings. This low rating may be due to not doing one thing great, but doing most things consistently, except stealing bases. He had only five last season, which makes running the bases his only weakness.

Though 13 longballs may be about his max, his 2.2 barrel percentage and 24.7 hard-hit percentage don’t bode well for him increasing his homers. The shortstop position is deep this season, with many exceptional players. So fantasy managers can wait to grab their starter until later in the draft. This situation makes Wilson a prime target who can outperform his 165th ADP.

Colson Montgomery – SS/3B, Chicago White Sox (ADP: 182)

Colson Montgomery has had an up-and-down minor league career, but his massive power offers high rewards for fantasy managers with the guts to wait on the White Sox shortstop. Last season, he hit 11 home runs in 242 Triple-A plate appearances and 21 homers in 284 MLB plate appearances. His metric percentages (14.5 barrel, 44.5 hard-hit, 31.2 flyball, and 48.6 pull) are impressive for the shortstop position.

The downside to Montgomery is that his power comes at a cost, with his batting average hanging around the low .200s. When the South Side of Chicago shortstop wasn’t hitting homers, he was below average, posting a .263 BABIP. Montgomery’s high-risk, high-reward fantasy production is boosted by being multi-position eligible. Fantasy baseball managers can also slot Montgomery into the third base position, which his power can well account for.

The White Sox shortstop comes in right behind Wilson in our consensus rankings at 17th, though two of us ranked him a spot higher, me included. When drafting Montgomery, take into account that he will boost your home runs and RBIs, but will hurt you in batting average and on-base percentage.

Konnor Griffin – SS/OF, Pittsburgh Pirates (ADP: 255)

There is massive hype revolving around the Pirates’ 19-year-old prospect. The ninth overall pick in the 2024 MLB draft was electric in his only minor league season. Last year Griffin slashed .333/.415/.527 in Single- and Double-A. He also added 21 home runs, 117 runs, 94 RBIs, and 65 stolen bases. These statistics position the five-tool player as comparable to Mike Trout, which is great news for fantasy baseball managers.

Once Spring Training ends, Griffin may fly up draft boards. The hesitation in drafting the prospect higher than his 23rd shortstop ranking is because there is uncertainty around whether he will make the Opening Day roster. If he doesn’t make the roster, then it shouldn’t be long for Griffin to make his MLB debut.

If the Pirates are serious about wanting to put the best offense together to aid phenom Paul Skenes and their young starting rotation, they can’t believe Nick Gonzales is their best bet at shortstop. However, Griffin can also play in the outfield, giving the Pirates multiple ways to utilize their prospect.

If your league drafts early in Spring Training, you can add Griffin as a backup in the later rounds. As we get closer to the season, the likelihood is that fantasy managers will lose the luxury of waiting to draft the five-tool player. Keep your ears out for the Pirates’ plans for Griffin throughout Spring Training.

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