Alex Bregman Just Raised The Stakes For The Cubs This Weekend

As Bregman makes his comeback in a high-stakes Cubs-Red Sox doubleheader, questions loom over playoff positioning and how weather woes might further complicate the schedule.

Alex Bregman is back in the Cubs’ lineup, and the timing could hardly be better for a club that has spent the last few days looking stuck in neutral at the plate.

Less than a week after taking a foul ball to the face last Sunday, Bregman will return Friday in Game 1 of a doubleheader against the Boston Red Sox as the designated hitter. Matt Shaw will handle third base.

Bregman had already resumed hitting and running the bases, but there was still real uncertainty about whether he’d be ready to take the field at third. Instead, he’s back in action far sooner than anyone reasonably expected after a scare that put his season and playoff availability in doubt.

That matters even more given how much the Cubs needed a jolt. They struggled to score over the past three days against the Miami Marlins, and Bregman’s return gives them a needed lift as they try to sort out the final stretch of the regular season.

The Cubs already punched their playoff ticket Thursday, and Pete Crow-Armstrong joined the 40-40 club, but the bigger question now is where they’ll begin October. As of Friday morning, Chicago would be headed to San Diego to face the Padres in the NL Wild Card series. The Cubs enter the day one game behind San Diego for the top Wild Card spot.

There’s also the weather hanging over this series. A nor’easter is forecast for the Boston area this weekend, and that has thrown the rest of the schedule into doubt.

Right now, the Cubs’ plane is slated to leave for Florida after Friday night’s game. The expectation is that both teams will have Saturday off before finishing the regular season Sunday in Tampa Bay.

Friday’s scheduled starters are Clay Holmes and David Peterson. If the teams do end up playing Saturday, the current plan is for Shota Imanaga to pitch on short rest, something Craig Counsell has already made clear he’s not happy about because of the load it would put on the pitching staff before the playoffs.

The Cubs and Red Sox were both willing to move the series to Wrigley Field, with Chicago offering to reimburse Boston for the lost revenue, but the Padres and Phillies objected to that setup. Both of those clubs have understandable reasons to push back, but in this case it feels like MLB should have gone with the option the teams actually involved in the series were willing to accept.

In Other News...

Ian Happs Wrigley Gesture Felt Bigger Than A Normal Thank You

Ian Happ has never been hard to spot as one of the faces of the Cubs, but his latest Wrigley Field gesture landed with a little extra weight. After a recent game, he tossed a ball into the stands with a thank-you message and $300 attached for the fans, a small act that felt meaningful for a player who has spent his entire big league career in Chicago since being drafted in 2015.

It also came with an undercurrent that Cubs fans can feel even if nobody is saying it out loud. Chicago has already wrapped up a postseason spot, but there is no guarantee the club will host a playoff game at Wrigley, and Happ is heading toward free agency after the 2026 season. So a simple thank-you might have carried a subtler message too, because there is still real uncertainty about whether he will get another regular-season sendoff at the ballpark he has called home for so long. [Read more 🡒]

Cubs Could Fix A Quiet Lineup Flaw With Their Next Outfield Move

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What makes the discussion interesting is the fit of the lineup itself. Chicago already has the power to do damage, but there is room for a player who can help manufacture runs with small ball, situational hitting and steadier at-bats when the game tightens. If the Cubs go shopping for corner help, the best addition might be the kind that balances the order more than it headlines it. [Read more 🡒]

Anthony Rizzo Just Sparked A Cubs Playoff Debate Fans Will Hate

Anthony Rizzo has reignited a familiar October debate around the Cubs, floating a playoff approach that would prioritize the most favorable path once a berth is secured. The former Cubs first baseman suggested that after clinching, the team should back into a matchup with the Braves on the road rather than chase a different bracket, a take that immediately puts roster health, matchup preferences and the value of home-field edge under the microscope.

David Ross, his podcast co-host and former Cubs manager, pushed back on that idea and made the case for keeping the game in Chicago, where Wrigley Field can matter in a short series. The larger concern hovering over the conversation is the possibility of a first-round trip into a hostile setting, with the Phillies looming as the kind of opponent no one around the Cubs would want to see under those conditions. [Read more 🡒]