Bill Simmons’s Red Sox Tweets Timeline Captures Rollercoaster Second Half of Season

The Boston Red Sox are back in the hunt for the postseason for the first time since 2021 and it’s gotten Bill Simmons back into baseball. After a 30-35 start and a big shift in vibes following the Rafael Devers trade, Simmons has been tweeting more frequently about his favorite baseball team.

Unfortunately, that has often led to immediate consequences for the team on the field. Almost as if his being happy about the team on social media has resulted in some sort of jinx. Here’s a quick recap of how things have been going for the team as he has posted through the second half of the season.

July 18

The Red Sox had won their last 10 games before the All-Star break and are just a game behind the New York Yankees in the AL East standings. (Both teams trail the Blue Jays) The day the season resumed Simmons tweeted that he was excited about the team. They lost to the Cubs that afternoon.

This is the most excited I’ve been about the Red Sox coming out of the All Star Break in 7 years. They better not F with this team.

— Bill Simmons (@BillSimmons) July 18, 2025

July 21

Boston suffers a “new dumbest loss of the season” in a bizare walk-off loss to the Phillies. They’re now two games behind New York.

July 22

Boston loses for the fourth time in five games. “Was way more fun when the Red Sox were playing the sh—- NL teams.”

July 28

The Red Sox had just won two games against the defending World Series champion Los Angeles Dodgers, but there’s chatter about a lockout. just as “MLB is getting its mojo back.”

August 1

Boston has won three straight, but they didn’t do anything at the trade deadline. Simmons hopes “the Red Sox owners get explosive diarrhea this weekend.”

August 5

The Yankees drop their fifth straight game. The Red Sox win their seventh straight. Boston now has a 3.5-game lead over New York and are three games behind the Blue Jays. Doctor Bill (his father) is very excited about Boston Blue. After sending this tweet the Red Sox would drop four of their next five games. Meanwhile, the Yankees have won eight of their last 11 since this tweet.

I can’t get enough of these Yankee games — this is better than Season 5 of Seinfeld.

— Bill Simmons (@BillSimmons) August 6, 2025

August 9

The Red Sox had won 10 of 12 games and Roman Anthony hit a double in the ninth inning against the Padres to tie the game 4-4. Simmons hit send shortly before the Padres scored in the 10th to win the game. They have dropped seven of 10 games since he tweeted this:

The Roman Empire Year One!!!!!!!

— Bill Simmons (@BillSimmons) August 10, 2025

August 11

Roman Anthony hits a two-run home run in the seventh inning to bring the Red Sox within one of the Astros. After an all-caps “WE ARE ALL LIVING IN THE ROMAN EMPIRE” tweet no one else scores in the game and the Astros win 7-6.

August 17

The Red Sox took a 3-1 lead into the eighth inning and lost 5-3 to the Miami Marlins. It’s the “Worst Red Sox loss in awhile!”

August 19

The Orioles, who can “f— off,” beat the Red Sox 4-3 in 11 innings. It is the Red Sox’s third straight loss.

Meanwhile, Aaron Judge returned to the Yankees lineup and hit one of the team’s nine home runs against the Rays as New York won their fourth straight game. New York is now back ahead of Boston in the standings.

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