Cubs Face A Stressful Fenway Twist At The Worst Time

As a looming noreaster threatens to disrupt the critical final stretch of MLB's regular season, the Cubs and Red Sox must navigate potential delays that could impact their playoff hopes and seeding.

The last week of the MLB regular season is here, and a storm system in New England could make an already tight playoff race even more complicated.

The Cubs enter the final three games holding the National League’s top wild-card spot over the Padres on a tiebreaker, with the Phillies sitting one game back. Chicago closes the season with a three-game series at Fenway Park against the Red Sox, a matchup that matters on both sides of the bracket. Boston has already clinched a playoff berth and sits in the AL’s second wild-card spot, but its seed is still unsettled.

That creates a scheduling headache MLB would rather not deal with. The regular season ends on Sunday, and the wild-card round starts two days later, so the league needs the Cubs-Red Sox series to finish cleanly and on time.

The weather forecast is not encouraging. An early-season nor’easter is forming in New England, and it could stretch into a multi-day event by the time the series begins.

NBC 10 Boston reported that its model guidance points to a familiar New England storm setup: strong wind, heavy rain, and the possibility of coastal flooding. The full moon later in the week only raises the concern for moderate or major flooding along the coast.

Small changes in the storm’s track and strength will matter, but the current expectation is for a significant system to bring soaking rain and gusty winds, especially near the shoreline.

If the weather does force a delay or cancellation, MLB could be staring at a late-season makeup scenario. That would bring back memories of the Mets and Braves in 2024, when heavy rain in Atlanta wiped out two games late in the season and forced the teams into a Monday doubleheader after the regular season was supposed to be over.

That situation carried far more drama. In 2024, playoff lives were on the line.

The stakes were simple: split the doubleheader and both teams would reach the postseason; one team sweeping both games would send the other home. The Mets won the opener, the Braves took the second game, and both clubs advanced.

Atlanta then got swept by the Padres in the wild-card round, while New York made a run to the NLCS before falling to the eventual World Series champion Dodgers.

This year’s setup is less severe, but still far from ideal. The Red Sox have already punched their ticket, and the Cubs are one win away from clinching theirs.

Chicago’s spot in the field looks safe, but its seeding is still unresolved. Even so, MLB has no interest in letting weather create a late-week mess that could turn into an unwanted doubleheader and force teams to play under the kind of disadvantage the league wants to avoid.

In Other News...

Payton Tolle Just Gave Red Sox Fans Another Reason To Love Him

Payton Tolle had more than the usual rookie celebration in his pocket when the Red Sox wrapped up their postseason spot. The left-hander spent part of the clinch festivities speaking with reporters, and he came off as a pitcher who not only knows how far he has come since 2025, but also understands why Bostons run matters so much right now. His 2026 season has turned into a strong one, with a 9-6 record, a 3.02 ERA and 166 strikeouts across 25 starts.

For a club already looking ahead to October, Tolles growth has become another reason the fan base has taken to him so quickly. He did not sound like someone content to simply enjoy the moment, either, as he expressed optimism about the Red Soxs playoff chances and the kind of baseball this group can still play. For a team built around believing the next step is still possible, that kind of confidence from a young arm only adds to the intrigue. [Read more 🡒]

Red Sox Could Soon Face A Tough Garrett Whitlock Decision

Garrett Whitlocks future keeps circling back to the same question for the Red Sox: is he more valuable as a high-leverage reliever, or could he bring even more to the club if he moves into the starting rotation? Whitlock has the kind of pitch mix that can make the idea tempting, and Boston has long appreciated the versatility he brings to the staff. With his contract situation giving the team options for 2027 and 2028, this is the sort of decision that could shape not just his role, but part of the clubs long-term pitching plan.

The appeal is obvious, but so are the concerns. A move to the rotation would ask more of Whitlock physically, and health has to be part of the conversation whenever Boston weighs changing a pitchers usage pattern. For now, the Red Sox can keep exploring the possibility without rushing into anything, but the fact that the discussion is even on the table suggests this could become one of those strategic calls that defines how the roster is built in the seasons ahead. [Read more 🡒]

Red Sox Suddenly Face A Pre-Playoff Seeding Problem At Fenway

The Red Sox have already punched their ticket to October, but the final three games at Fenway Park suddenly carry a different kind of importance. Boston is set to close the regular season against the Cubs, and a significant storm forecast could put the schedule in flux just as the club is trying to settle into its playoff rhythm.

MLB may be forced into some awkward juggling if the weather knocks games off the board, with postponements and possible makeup plans creating the kind of late-week uncertainty teams prefer to avoid. Doubleheaders could enter the conversation, and so could the impact on rest before the postseason begins, leaving Boston with one more variable to manage before the real games start. [Read more 🡒]