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Come Fan with UsTuesday, June 23, 2026

5 bets the Boston and Philadelphia mayors should make for Super Bowl 52

We need to raise the stakes more than Rocky statue vs. Rocky statue.

Benjamin Franklin statue at the Franlin Institute...
Benjamin Franklin statue at the Franlin Institute...
Photo by John Greim/LightRocket via Getty Images

Political sports bets are perhaps the friendly wagers that so often do not live up to their potential. We could be doing so much better than these creampuff wagers where we send a case of beer to the other state or what have you.

Sometimes it does get pols in trouble, like in 2009 when the governors of Florida and Alabama made this wager on the SEC Championship Game that year.

Gov. Bob Riley made the usual friendly bet with Florida Gov. Charlie Crist on last weekend’s Southeastern Conference football championship game: a crate of Florida oranges versus ribs from Dreamland BBQ in Tuscaloosa.

Riley took some flak at the time from gambling opponents, and asked Florida not to send the oranges.

The actual mayor of Boston is too chicken to make bets anymore, given that he lost two in a row. So it’s up to Philadelphia Mayor Jim Kenney and Bill Carpenter, mayor of Brockton, Massachusetts — about 45 minutes away from Boston — to make the wager for Super Bowl 52.

Brockton is the birthplace of famed heavyweight champion Rocky Marciano. Both cities have their own Rocky statue — one is of the real-life Rocky, the other is of the film version.

But we think they can do better. There’s something political bets often lack — I’m talking bigger stakes. Since Boston’s mayor isn’t really a betting man anymore, we’ll let Carpenter put up some Boston-affiliated wares for the wager.

So here are a few things that the mayors could bet that would make things much more interesting. Put up or shut up. This is football after all.

1. Mayors should have to only eat the opposing city’s staple food every meal for a week

If the Eagles win, Carpenter should have to eat a week’s worth of Philly cheesesteak with all the Cheez Whiz money can buy slathered all over ‘em. But what Mayor Kenney would dine on if the Patriots win? That’s a more elusive proposition because Boston doesn’t really have a staple food. New England Clam Chowder’d probably be the go-to, so here’s hoping the guy likes soup.

2. Trade their best statues

Both mayors are wagering what to dress their statues in, but why don’t they just put staple statues on the line.

Kenney can put ol’ big Ben Franklin on the table ...

Benjamin Franklin statue at the Franlin Institute...
Photo by John Greim/LightRocket via Getty Images

... and Carpenter can wager Paul Revere.

Boston Exteriors And Landmarks
Photo by Paul Marotta/Getty Images

3. Mayors join in antics with the other city’s best mascots

Don’t lie to yourself, you’d love to see a mayor dressed to the nines in 18th century garb firing one of these bad boys with the End Zone Militia.

Revolutionary Patriot reenactors fire guns after a New England Patriots score at Gillette Stadium
Photo by: VOA/UIG via Getty Images

And who among us wouldn’t like to see Carpenter on the back of this thing with Philadelphia’s famous plush mascot riding around Citizens Bank Park.

Washington Nationals v Philadelphia Phillies
Photo by Rich Schultz/Getty Images

4. Mayors have to work a famous line from a movie into their next speech

Maybe it could be in a debate, or in some other speech when witticisms are needed, but I would very much like a politician to ask their opponent if they like apples. The scene comes from the lovely Boston-based movie, Good Will Hunting.

This would be a pretty quick burn for Kenney to work into a speech. With the best speechwriters in Philadelphia at his disposal, he should be able to figure this out should the birds lose.

Carpenter’s task would be much easier. The line would only be one word long.

5. Sing a song from a favorite music act

In a live televised performance, I think the losing mayor should have to sing the song of note from one of the opposing city’s most renowned musical acts.

For Kenney, get the rags out. It’s “Dream On” time.

For Carpenter, there are plenty of acts to pick from. In a perfect world, it’d be the melodic stylings of Boyz II Men.

I doubt he can harmonize like the Boyz do here, but we can certainly watch him try. I’m shooting for entertainment value here, and we’ve got that.

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