Shane "Sugar" Hennen documented his rising stakes in sports betting on an Instagram account he called #bestthateverdidit. Read more Anton Klusener/ Staff Illustration. Photos: AP; Getty Images; @bestthatevadidit; @sugarshanewins

by Ryan W. Briggs and Max Marin Updated Oct. 28, 2025, 5:00 a.m. ET | Published Oct. 27, 2025, 5:27 p.m. ET

On the green felt of a Bellagio baccarat table, Shane “Sugar” Hennen flaunted $3,125 in winnings from a Pittsburgh Pirates game in June 2014.

It was a drop in the bucket for Las Vegas moneylines. But on Instagram, Hennen called it “#2dayswork.”

He was burnishing his brand as a high-stakes gambler, documenting his exploits under the handle @bestthateverdidit. Within a decade he would place bets 100 times larger than that on a Saturday n

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