The Chicago Cubs have been the toast of Windy City baseball for most of the last decade, but the Chicago White Sox are catching up.

Both Chicago teams have reason to believe the shortened 2020 MLB season provides an opportunity to challenge for a division title and return to the postseason. But of the two teams, which has a better chance to win the most games and pay out an MLB futures betting prop?

DraftKings has posted props matching teams and win totals for the 2020 MLB regular season. One of those props includes a head-to-head wins wager for these Chicago rivals.

MLB odds current as of publication

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Comparing The Rosters

The Cubs ranked 10th in runs scored and sixth in home runs in 2019, and nearly everyone is back for perhaps one final hurrah before the team gets broken up due to expected salary explosions. Kris Bryant will bat leadoff, a great move that puts him in front of a wicked Anthony Rizzo-Javier Baez-Kyle Schwarber lineup. The offense could dramatically drop in production after the first 4-5 hitters, however.

The rotation begins with Yu Darvish, who really struggled early in 2019 but was one of the game’s dominant hurlers the second half of the season. Veterans Kyle Hendricks and Jon Lester are again in the fold, and the bullpen was top 10 last year – it should be better if closer Craig Kimbrel recovers from a terrible 2019.

The White Sox went 72-89 last season, but that was 10 games better than 2018. They seek their first above-.500 campaign since 2012 and first playoff berth since 2008. Last season was an improvement, and this offseason was a sign of better things to come.

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The White Sox added slugger Edwin Encarnacion, a consistent 30 HR, 100 RBI contributor over much of the past eight seasons. They secured the top free-agent catcher on the market in Yasmani Grandal. And they added much-needed pitching depth in Dallas Keuchel and Gio Gonzalez. Keuchel, a former Cy Young Award winner, joins Lucas Giolito atop the rotation.

The Sox still have questions, including the lower-half portion of the starting staff and which Giolito will show up (he was a Cy Young candidate through eight starts in 2019 before fizzling out). They have speed at the top and bottom of the order, and power in the middle.

Matching up both teams, the Cubs have the better batting order. The White Sox might have a higher ceiling at starter, but the Cubs lineup is sounder. Each team is above-average in the bullpen, but the Cubs again have the slight edge.

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Comparing The Schedules

The NL Central and AL Central are matched up against each other in interleague action. But one division is stronger than the other.

The Twins and Indians are expected to clash for the AL Central crown, but the White Sox are a darkhorse in the field. After that, it gets weak with the Royals and Tigers. In the NL Central, four of the five teams are on nearly equal footing – the Cubs, Cardinals, Brewers and Reds could all stake a claim. Only the Pirates are longshots, and they’re better than Kansas City or Detroit.

The White Sox will have to deal with the Cubs’ rivals, and vice versa, but when it comes to division strength, the NL side has the depth.

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The X-Factor

Staff aces need to get it done for playoff teams. Each team has a guy it really needs to take that mantra and perform for a complete season.

Darvish was dominant over his final 11 starts of 2019, averaging nearly eight innings per outing while amassing 118 strikeouts to just seven walks and a 2.76 ERA. He’s a four-time All-Star and even took second in AL Cy Young voting in 2013, so we know it’s in there.

Giolito was unstoppable in the first half of 2019, allowing just six runs over his first eight starts with 65 strikeouts. He faltered late but still went 14-9 with a 3.41 ERA. He ranked No. 3 in swing-and-miss pitches, but can he regain his form for his third season as an MLB regular?

Whichever ace delivers gives his team a big, big MLB betting boost.

The Pick

The White Sox have pop and some speed, but the Cubs appear to have the more balanced, better order from top to bottom. The same could be said for the rotation and the bullpen. In other words, the Cubs are better than the White Sox.

But when it comes to total wins, it could be close. The NL Central offers a tougher day-in, day-out schedule for the North Siders. The Sox might have a higher overall ceiling than the Cubs, too.

But the Sox feel like a team you can’t count on – yet. With the high odds they’re showing in AL pennant and World Series betting futures, they’re a great flyer to do something special. But when it comes to simple wins, the Cubs are the safer, and better, bet. Wager on the Cubs to win more games in 2020 with DraftKings .