The 2026 MLB Playoffs continue with more Divisional Series action, giving us one game to target for daily fantasy contests. We’re going to be using DraftKings pricing to build the best lineups to try to cash in on a large-field tournament. Don’t forget to check out our MLB daily trends page for game odds, data, and insights.
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Up to $1,500 in Bonus Bets if Your First Bet Doesn't Win*
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On the Thursday slate, we’ve got one game on tap: Guardians-White Sox. That means we have to stick to the single-game slate for this one. With that in mind, let’s dive into my best DFS picks for the Divisional Series of the 2026 MLB Playoffs.
MLB Playoffs DFS Picks
| Pos | Player | Matchup | FPPG | Salary |
|---|---|---|---|---|
| MVP |
👑Parker Messick |
CLE @ CWS | 19.4 | $18,600 |
| UTIL |
![]() Jose Ramirez |
CLE @ CWS | 8.3 | $8,800 |
| UTIL |
![]() Chase DeLauter |
CLE @ CWS | 7.8 | $7,600 |
| UTIL |
![]() Brayan Rocchio |
CLE @ CWS | 6.8 | $6,000 |
| UTIL |
![]() Patrick Bailey |
CLE @ CWS | 4.4 | $4,400 |
| UTIL |
![]() Braden Montgomery |
CLE @ CWS | 6.0 | $4,200 |
Parker Messick (CPT) – CLE/SP ($18,750)
Parker Messick is expensive at $12,500, but I’m still willing to play him at “Captain,” where both his fantasy points and salary is 1.5x. That’s because he pitched like an ace this season, putting up a 2.56 ERA and a 1.06 WHIP with a 25.8% strikeout rate and a 6.6% walk rate. This includes excellent advanced metrics, as highlighted by a 3.54 SIERA.
Messick started in Game 1 of this series. He got off to a terrific start, but ran into trouble and was pulled early. He finished with 4.1 innings, four hits, two earned runs, two walks, and six strikeouts. The upside is there against this strikeout-prone White Sox lineup. Messick is capable of punching out eight batters in this one, giving him the highest ceiling on the slate. That’s why I’m firing him up at captain.
Jose Ramirez (UTIL) – CLE/3B ($8,800)
I’ll add Jose Ramirez, who got on track at the plate on Wednesday night, going 2-for-4 with two runs and two RBI. We all know about his long track record, so even though he had a disappointing season, he’s always capable of getting on track at the plate.
With a power and speed profile, Ramirez is worth paying up for, especially since this is a game that I think the Guardians will win. Ramirez comes at a better value than other sluggers in this game, including Miguel Vargas and Munetaka Murakami, making him worth firing up here.
Chase DeLauter (UTIL) – CLE/OF ($7,600)
Chase DeLauter has gone 3-for-8 with two runs and one RBI in the last two games. This comes after he had a terrific rookie season, where he hit .287 with 16 homers and 11 steals in 495 at-bats.
What’s great about pairing DeLauter with Ramirez is that he hits right behind him in the lineup. That’s a ideal stack partner when targeting Guardians’ hitters in this one.
Bryan Rocchio (UTIL) – CLE/SS ($6,000)
I’m including Bryan Rocchio here due to salary relief. He also is a sneaky stack partner for Ramirez (2nd) and DeLauter (3rd), since Rocchio hits in the No. 9 spot. That creates a scenario where Rocchio can be leading off an inning, getting on base, and then driven in by Ramirez or DeLauter.
Rocchio had a bit of a power surge by his standards this year, homering 15 times in 534 at-bats. He had two hits and an RBI on Wednesday, so perhaps he’s getting hot at the plate.
Patrick Bailey (UTIL) – CLE/SS ($4,400)
Patrick Bailey hits in the No. 8 spot, making him worth firing up to finish up our Guardians stack. Bailey homered nine teams this year. He’s also coming off a big game on Wednesday, going 2-for-4 with one run.
Bailey is a bet on salary relief here, since I want to jam in Messick+Ramirez+DeLauter.
Braden Montgomery (UTIL) – CHW/OF ($4,200)
With the way I built this lineup, I have to use my last slot on a White Sox hitter, since you’re only allowed a max of five players from the same team per entry. Braden Montgomery is the best choice at $4,200, since he has prospect pedigree with some pop.
Montgomery has gone 1-for-7 with two runs and two RBI in his last two games. As a switch-hitter, he’s in a good spot against lefty Parker Messick.
Photo Credit: REUTERS





