St. Pete Donald Trump supporter sued for reneging on election night bet sees victory after court reversal
President Donald Trump walks across the South Lawn of the White House in Washington, Saturday, July 11, 2020. Trump was returning from a visit to nearby Walter Reed National Military Medical Center in Bethesda, Md. Image via AP Photo/Pablo Martinez Monsivais

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Sean Hynes narrowly avoided jail time and convinced a judge to toss the case.

A St. Petersburg man who bet a former friend $100 that then-President Donald Trump would defeat now-President Joe Biden might’ve lost the bet, but he won in court.

Pinellas County Court records show Sean Hynes narrowly avoided jail time after missing a payment deadline. Hynes had agreed to pay on the bet, plus interest, during court-ordered mediation in March. When he didn’t pay by November, a judge warned he could face jail time. Then Hynes filed a motion to dismiss the whole case on the grounds that the bet was illegal.

“The Court agrees,” Judge Edwin Jagger wrote in his ruling. “Since the basis of the parties’ agreement was expressly ‘void’ and of no effect Under Florida law, and generally contrary to the public policy of the state, so too is the judgment.”

Hynes made an Election Day bet with former friend Jeffery Costa, who lives in Georgia. Hynes bet Costa $100 that Trump would win. Costa chose Biden. But amid Trump’s lies that the election was somehow fraudulent and stolen from him, Hynes refused to pay. He held out belief that the results would be overturned.

But even after Biden was sworn in, Hynes refused to pay. Costa took him to court in early 2021 and in March a judge ordered Hynes to pay $207.50 by Oct. 9.

When Hynes didn’t pay, a judge ordered him to show cause as to why he couldn’t pay by Nov. 1. If he didn’t, Hynes was told, he could face fines or jail.

“Pardon the drama, but I believe this case has gone far enough, wasted enough resources and needs to be put to rest, as we all value more important things in life,” Hynes then wrote to the court. “While I may be ‘liable’, the approach has been immoral and is not about the money, the plaintiff does not need it. It’s about ego. I know you don’t rule on ego, but I would hope you would dismiss the case on the grounds that the plaintiff entered an illegal contract.”

Daniel Figueroa IV

Bronx, NY —> St. Pete, Fla. Just your friendly, neighborhood journo junkie with a penchant for motorcycles and Star Wars. Daniel has spent the last decade covering Tampa Bay and Florida for the Ledger of Lakeland, Tampa Bay Times, and WMNF. You can reach Daniel Figueroa IV at [email protected].


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