How I Won a Whopping $63.60 Betting on Sports

The handicapping service Jambos is designed to give gamblers a leg up. It might look completely different after the Super Bowl

- IRA BOUDWAY With Eben Novy-Williams

My experiment as a Jambos bettor began on New Year’s Eve. It didn’t get off to a great start. Jambos is a handicapping service, known to sports bettors as a “tout,” that sells picks for a fee; I paid $250 for a week’s worth. Every day around 11 a.m., Jambos would alert me that the day’s betting suggestions were available. There might be a handful or dozens, depending on the season and the schedule. On this day there were 13, including that the Kentucky and Virginia Tech football teams would score fewer than 47 points combined in the Belk Bowl.

Picks in hand, subscribers place the suggested wagers with bookmakers of their choice. Then, in theory, because Jambos has crackerjack statisticians running elaborate models, bettors win more often than they lose.

My plan was to bet on every wager that Jambos suggested in a week. Bloomberg Businessweek would cover any losses, and profits would go to charity. I sold this to my editors as a firsthand exploration of the mainstreaming of the handicapping business, and, somehow, they said yes.

Sports betting has come out of the shadows in the U.S. since a Supreme Court ruling in 2018 that opened the way for the industry outside of Nevada. Fourteen states now allow sports gambling. Together, they’ve taken more than $15 billion in wagers since the ruling, according to the American Gaming Association. Sports leagues, which fought against legal betting for years, are signing marketing deals with casinos.

When Jambos began selling picks in August, it promised to be a new kind of tout for a new era of sports betting. Would I, a novice, be able to execute the Jambos system? (Sorta.) Would Jambos live up to the hype? (Kinda.) Would I make money? (Yes.) Would I find myself frantically scrolling through my phone for a bookie that would give me under 47 on the Belk Bowl? (Yes.) Would it be any fun? (Do you like spreadsheets?)