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Bill Simmons’s Eight Tips for Cubs Fans

The Red Sox die-hard knows what it’s like to wait a lifetime for a World Series run


Bill Simmons’s wait for a Red Sox World Series win became the subject of his first book: Now I Can Die in Peace. As a Boston fan since birth, he knows how crushing the MLB playoffs can be. Cubs fans know that heartbreak just as well, but they haven’t yet experienced the thrill of victory (at least, not for 108 years). Is this the year?

On this week’s Any Given Wednesday, Bill gave his advice to the Cubs fans yearning for a title on the eve of the playoffs.

Bill’s Advice for Cubs Fans

Bill also had Seattle Seahawks wide receiver Doug Baldwin and actor Joel McHale on the program to talk about the NFL. In the mailbag segment, the two were asked: Does the entire league really hate the Patriots?

Their response, in unison: Yes.

Mail Bag With Doug Baldwin and Joel McHale

Then, Michael Rapaport picked the week’s winners and losers with Bill. Their first subject: Tiger Woods and his disappointing Ryder Cup.

Winners and Losers With Michael Rapaport: Tiger Woods

The two then crowned Vin Scully, the one 88-year-old we can all agree on, a winner.

Winners and Losers With Michael Rapaport: Vin Scully