Of course, the 2026 MLB season won’t end today, as only a handful of teams have even reached the 54-game (one-third) mark of the regular season. However, it’s noteworthy that if the season did end today, both the Chicago White Sox and the Minnesota Twins, who finished with the two worst records in the American League last season, would be in the playoffs.

The teams will face off for the first time this season at 2:10 p.m. ET, marking the start of a four-game set on the South Side of Chicago.

Anthony Kay will start the opener for the White Sox, and Zebby Matthews will get the call for the Twins.

Let’s break down this matchup with some odds and lines at DraftKings Sportsbook.

Minnesota Twins at Chicago White Sox prediction, preview

Minnesota entered the season with low expectations after selling several of its best assets at last summer’s trade deadline, but new manager Derek Shelton has done a tremendous job, and after winning 10 of their last 14 games, the Twins have climbed to 26-27. Their offense has remained relatively consistent despite all of their trade deadline departures, and Byron Buxton, who’s been mostly healthy, has produced arguably the best season of his career. More notably, Minnesota’s rotation has made strides; it finished 23rd in ERA in 2025 before jumping all the way up to ninth so far this season, as Taj Bradley and Bailey Ober have both had strong seasons to complement incumbent staff ace Joe Ryan. While the Twins’ bottom-10 bullpen is still an issue, Anthony Banda will likely bounce back at some point, given the pivotal role he played on the Los Angeles Dodgers’ 2024 title team.

Chicago showed some signs of progress last season after the All-Star break, producing a 28-37 record in the second half of the season. In 2026, the White Sox started just 7-14, but since then, they have had a monthlong stretch at a 99-win pace, going 19-12 and climbing briefly above .500. In particular, their offense has jumped from the league’s third-worst last season to its ninth-best so far, as Munetaka Murakami (.235/.376/.530 slash line with an American League-leading 17 homers) has been a revelation. He, Miguel Vargas, Colson Montgomery, and Chase Miedroth have demonstrated enough for Chicago to believe that it has its infield of the future in place. The White Sox’s offensive growth alone has been enough to lead to wins, as neither the rotation nor the bullpen has made significant strides after last season.

Matthews wasn’t good last season, pitching to just a 5.56 ERA in his 16 starts, but he had an excellent first two starts of the 2026 campaign, giving up just two earned runs in 13.0 innings while walking one and striking out 11. He’d also given up two or fewer earned runs in four of his final five starts for Triple-A St. Paul before earning promotion back to the majors. Though his two starts represent a small sample size, there’s reason to believe that his form could be sustainable, as his Statcast expected numbers are pretty elite and he’s generated more break on his curveball and slider than he did last season. Even in 2025, he excelled at inducing chases and whiffs, and while hitters haven’t missed much so far in 2026, that could change this afternoon, given that Chicago has been the most whiff-prone team in baseball. The White Sox could also mitigate his tendency to give up fly balls, given that they hit grounders at the sixth-highest rate. I’m still not too high on a guy who had a 22nd-percentile barrel rate last season against a team that ranks fifth in that stat this season, but a 26-year-old improving from pitiful to serviceable wouldn’t be a shock. Matthews has also been slightly better on the road throughout his career, and while Chicago has been better at home, it has also been worse against righties.

I’m not sure Kay has an advantage in the starting pitching matchup, but he has had a strong month, pitching to a 2.11 ERA across four starts. He also had a 1.74 ERA across 24 appearances in Japan in 2025, finishing second in the Central League’s ERA title, so while he doesn’t have a lengthy track record of success in the MLB, he clearly has the tools to succeed at a top level. However, Statcast doesn’t paint such a positive view of his repertoire: his 5.93 expected ERA ranks in just the eighth percentile, and he’s also posted bottom-quintile whiff and strikeout rates. Given that Minnesota’s high whiff rate is one of its biggest offensive weaknesses, Kay represents a good matchup. Additionally, the southpaw has walked a lot of batters and given up a lot of barrels, and the Twins have already produced plenty of both as is. The splits are in Kay’s favor, but only ever-so-slightly, as Minnesota’s offense has performed similarly whether at home or on the road, and its platoon splits are insignificant.

Minnesota Twins at Chicago White Sox pick, best bet

Best Bet: Minnesota Twins Moneyline (-107)

I’m not overly confident in either of these starters or in the bullpens behind them, but the Twins are better-suited to get to Kay than the White Sox are to Matthews. They’re also in hotter form overall.

Strong Lean: Munetaka Murakami or Byron Buxton – Either Player 1+ Home Runs (-101)

This is a pretty aggressive line, but Murakami and Buxton rank first and third in the American League, respectively, in homers. Kay likes to offer predominantly four-seam fastballs to righties, and Buxton has a .583 expected slugging percentage this season against lefty four-seamers. Murakami’s expected slugging percentage against the righty four-seamers that Matthews relies on is even higher.