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Minnesota Twins vs. Chicago White Sox prediction, pick for Wednesday 5/27/26

Minnesota Twins vs. Chicago White Sox prediction, pick for Wednesday 5/27/26

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By: Bryan Armetta

Surprising postseason contenders are set to meet on Wednesday in the Windy City. The Twins (27-28), despite their sub-.500 record, are currently in sole possession of the American League’s second wildcard spot. As for the White Sox (27-27), it’s been a terrific month of May in the South Side. Which of these two division rivals will earn a series victory this evening?

Tonight’s game is a pick ’em, with the White Sox and Twins both priced at -110. The over/under is set at 7.5 runs. Below, I’ve laid out my preview, prediction, and best bet for Wednesday’s showdown between Minnesota and Chicago on DraftKings Sportsbook.

Twins vs. White Sox prediction, preview

Minnesota’s biggest weakness is pitching depth. After a solid first few arms, the rotation has been shaky in the back end. Getting some consistency out of Connor Prielipp could go a long way for the Twins. Through 29.0 innings, the 25-year-old has notched a 4.03 ERA, 1.17 WHIP and 30 strikeouts (9.3 K/9). He had been effective this season prior to last week’s poor showing vs. Boston (4.0 IP, 5 ER). There’s nothing the righty does exceptionally well, but he ranks within the top 70th percentile in hard hit rate (35.4%).

Limiting hard contact could prove key tonight against a lineup that loves to mash. The White Sox rank third in home runs (73) and seventh in slugging percentage (.397) among all MLB teams. Much of the credit goes to offseason acquisition Munetaka Murakami. The Japanese standout is slashing .234/.370/.547 with an American League-leading 19 homers this season. However, he’s joined by several other standout South Siders. Miguel Vargas (136 wRC+), Colson Montgomery (120 wRC+) and Sam Antonacci (118 wRC+) have formed a promising young nucleus.

Much like Minnesota, the White Sox aren’t blessed with an abundance of quality arms. Tonight, it’ll be David Sandlin making his major league debut at Rate Field. The 25-year-old, acquired last summer, is someone Chicago’s front office is high on. Looking over the numbers, it’s easy to see why. Through four starts this season with Triple-A Charlotte, Sandlin has recorded a 0.75 ERA, 1.25 WHIP and 17 strikeouts (12.8 K/9). The downside is that the righty isn’t someone that pitches deep into games. In each of his three seasons in the minors, he’s never tossed more than 106.2 innings. Don’t expect more than a handful of frames from the rookie on Wednesday.

The Twins don’t do anything particularly well on offense, but this group shouldn’t be slept on. They rank eighth in baseball with 254 runs scored this season, led by two-time All-Star Byron Buxton (143 wRC+). Although the loss of catcher Ryan Jeffers (hand) hurts, there’s enough lineup depth for Minnesota to remain a force at the plate. Still, there’s reason for some concern. Sandlin’s favorite secondary pitches are his curveball and slider. Twins batters own a .201 batting average and .282 wOBA against those two offerings.

Twins vs. White Sox pick, best bet

It’s never easy backing a rookie starter, especially in a division game. Regardless, it’s not as if Prielipp is the most experienced arm, either. Given the uncertainty for both sides on the mound, it’s only natural to side with the better, healthier lineup. In front of an energetic home crowd, the White Sox are poised to win this series tonight.

Best Bet: White Sox ML (-110)

Bryan Armetta is a New York-based writer that has spent over eight years in sports media. Working for DraftKings since 2024, he currently serves as a writer, editor and analyst for all things sports and pop culture. Bryan specializes in MLB, NBA, NFL, college sports and entertainment content. Prior to his time at DKN, he worked for MLB Network, NHL Network and SiriusXM Sports.
Disclaimer

I am a promoter at DraftKings and am also an avid fan and user and may sometimes play on my personal account in the games that I offer advice on. Although I have expressed my personal view on the games and strategies above, they do not necessarily reflect the view(s) of DraftKings and do not constitute a representation that any particular strategy will guarantee success. All customers should use their own skills and judgment in building lineups. I may also deploy different players and strategies than what I recommend above. I am not an employee of DraftKings and do not have access to any non-public information.