Chicago Cubs biggest question for remainder of 2026 season revealed by team insider

The Chicago Cubs have a 98.6% chance to make the MLB Playoffs. In other words, the only realistic way in which they do not appear in the postseason is if they go on an all time run of futility and collapse. Jobs would almost certainly be lost on the coaching staff, and numerous players would be sent packing.

Realistically, Chicago is about to cruise into October looking to make some noise in the ultra-competitive National League. However, they are poised to do so as the league’s top Wild Card and not as a division leader.

The biggest question facing the Chicago Cubs is if they can catch the Milwaukee Brewers

At 74-54, Chicago has the fifth-best record in all Major League Baseball. However, they stand five full games behind the Milwaukee Brewers for first place in the National League Central Division. If they are unable to overtake Milwaukee, the Brewers will win the NL Central for the fourth year in a row.

According to Cubs insider Jordan Bastian, whether or not they can reclaim the division lead is the biggest question facing Chicago at this point in the season:

“A three-game losing streak back from June 7-10 knocked the Cubs eight games behind the Brewers in the NL Central. At that moment in time, Chicago’s odds of winning the division slipped to 5.5%, per FanGraphs.

“The North Siders played 21 games above .500 over the next 59 games (40-19) to not only strengthen their grip on a Wild Card spot but also pull within shouting distance of Milwaukee.

“The Cubs have a challenging schedule the rest of the way, but chasing down the Brewers remains a goal for a club that added two veteran starters — Kevin Gausman and Clay Holmes — at the Deadline, have an MVP contender in Pete Crow-Armstrong and boast baseball’s best defense.”

Despite their 40-19 run over their last 59 games, the Cubs picked up only three games on the Brewers. However, Chicago still has seven games remaining this season against Milwaukee, four of which will be played at home at Wrigley Field.

There is no argument that the Cubs boast a more potent offense. However, Milwaukee’s pitching staff has been far more dominant and, almost just as vital, healthy.

The division race could really come down to which of the two teams is able to finish the year with the more healthy pitching staff.

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