Neil’s Substack

Neil’s Substack

The Red Sox Won Themselves Into a Deadline Dilemma

Boston's historic surge has turned a lost season into a likely playoff run. Now comes the harder question: How much should the front office believe in it?

Neil Paine's avatar
Neil Paine
Jul 22, 2026
∙ Paid
Boston Red Sox first baseman Willson Contreras claps after getting to first base in the third inning. The Boston Red Sox played the Baltimore Orioles at Fenway Park on July 20, 2026. (Christian Kantosky/The Boston Globe via Getty Images)

As of roughly three weeks ago, the Boston Red Sox were one of the most frustrating experiences in baseball. A team that surged to the playoffs last year — and was supposed to be among the best again in 2026 — started the season so poorly that manager Alex Cora was fired before the end of April, and the team was also multiple games underwater with replacement Chad Tracy courtesy of additional losing months in May and June. Baseball logic dictated that the Sox would be shopping around some of their more attractive trade candidates before the Aug. 3 deadline, forcing fans to say goodbye to even more favorites in the name of future value.

But then, true to the form of a franchise that has oscillated violently between being unexpectedly good and unexpectedly bad almost continuously for 15 years now, Boston suddenly decided to rattle off their longest winning streak since Ted Williams was 27 years old. The streak has breathed life into the playoff odds for a team that down into the single-digits (which seemed generous) by late June:

It has also transformed the potential of this season at Fenway Park — in a good way, but also a confusing way, because of course it did.

User's avatar

Continue reading this post for free, courtesy of Neil Paine.

Or purchase a paid subscription.
© 2026 Neil Paine · Privacy ∙ Terms ∙ Collection notice
Start your SubstackGet the app
Substack is the home for great culture