BOSTON — In a city where the outcome was as certain as tomorrow’s sunrise, gamblers still found a way to make it weird. More than $172,000 changed hands on the crypto prediction platform Polymarket during Boston’s mayoral election, an election Michelle Wu was literally running unopposed.

By Election Day, Wu’s odds had hit a perfect 100 percent, yet bettors kept piling in, chasing microscopic profits like crypto day traders on caffeine.

Wu’s rivals, mostly ghosts from old ballots and creative write-ins, still attracted tens of thousands of dollars. The biggest shocker? Althea Garrison, a perennial Boston character, drew $70,105 in bets, quadruple Wu’s own $16,520 market.

Josh Kraft, who bowed out weeks ago after getting flattened in September’s preliminary (Wu 72%, Kraft 23%), still had nearly $17K wagered on him. Even the city’s former police commissioner and a random policy wonk named Jorge Mendoza-Iturralde saw action.

Totals:

Althea Garrison – $70,105 Jorge Mendoza-Iturralde – $39,628 Josh Kraft – $16,905 Michelle Wu – $16,520 Ed Flynn – $15,221 William G. Gross – $14,317

Why bet on a sure thing?

Experts call it “penny-flipping psychology.” MDN calls it what it is: degeneracy with better branding.

Wu celebrated her walkover victory at Grace by Nia in the Seaport, aiming fire at Donald Trump in a speech that could have doubled as a campaign ad for MSNBC. “Whether we will bow to a criminal who acts like a king,” she warned, as Boston’s traders quietly collected their 2 percent gains.

The 40-year-old mayor now enters four more years with zero opposition and full national attention, while Polymarket proves the obvious. Even when politics is boring, there’s always money in pretending it’s exciting.

Sources

Polymarket Boston Mayoral Election Market: https://polymarket.com/event/boston-mayoral-election

WCVB: "'Boston doesn't back down': Boston Mayor Michelle Wu attacks Trump in election night speech" (November 4, 2025): https://www.wcvb.com/article/boston-mayor-unopposed-election-2025/69254398

The Boston Globe: "Mayor Michelle Wu keeps staggering lead over Josh Kraft" (September 10, 2025): https://www.bostonglobe.com/2025/09/09/metro/boston-mayor-election-wu-kraft/

The Boston Globe: "Boston Mayor Michelle Wu officially claims second term" (November 5, 2025): https://www.bostonglobe.com/2025/11/04/metro/michelle-wu-second-term-election-national-figure/

WBUR: "An unopposed Boston Mayor Wu celebrates re-election victory" (November 4, 2025): https://www.wbur.org/news/2025/11/04/michelle-wu-boston-2025-mayoral-race