Amazing Gambling Story: The Man Who Turned $40 Into $48k Without Even Watching The Game

With close to $48,000 on the line from a $40 Same Game Parlay, any ordinary bettor might be inclined to watch their wager play out by tuning into the game on TV. For Kenny McAndress, he instead cashed the biggest gambling win of his life by following the box score on his ESPN app while watching a movie on the couch with his fiancé. Then again, McAndress is no ordinary bettor.


The man known online as @kiiLkenny hit the biggest Same Game Parlay we’ve ever seen here at back in April, during a regular season game between the Atlanta Hawks and Chicago Bulls that returned odds of +119239.

The selections - three in total - were so simple: Trae Young to score 40+ points with LaVine to do the same while also swishing five three-pointers. 

“There were just a bunch of indicators that highlighted the ‘BOOM’ potential of both guys,” McAldress said when asked what made him put together the parlay that night.

“I remembered a game the two played against each other a few years back that went to 2OT, both almost went for 50, and it was essentially 1v1 for the entire second half. So it felt like a good combo to run back for a Friday Night Bomb”

And what a bomb it was. Zach LaVine from the Bulls miraculously notched up his 40-piece before halftime, on the way to scoring 50 points for the game. For Young, though, things were much tighter. The Atlanta guard didn’t hold up his end of the parlay until a floater with 28 seconds left in the match secured a total of $47,735.52 for Kenny.

“Pretty tamed at first,” Kenny said upon reflecting back on his initial reaction once he landed the huge windfall. “Me and my fiance were watching a movie, so she had no clue what was at stake,” he said.

Once he had told his partner about the winning bet, disaster struck. The FanDuel Sportsbook app, which was used to place the huge parlay, crashed for close to 12 hours. 

“Luckily the money hit my account a few minutes later (after the crash), and then we proceeded to celebrate for like a week straight.”


The Philadelphia resident has become part of a tight-knit group of gamblers online who have grown communities around their big wins. For McAndress, however, that community has gone far beyond that of Twitter, with a nightly stream on Twitch originating in July 2020 called The Moonshot which pools the community together to discuss that night’s slate of games to gamble on with hundreds of viewers religiously tuning in.

“The #MoonieGang is everything to me, man” said the 28-year-old, referring to his loyal group of online stream followers.

“Gambling content has gone crazy on platforms like Twitch and Discord over the last six months, and I take a ton of pride in knowing that I was one of the first people to bring gambling-specific content to these platforms.”

It’s a sentiment that is often the running theme across notable bettors online that has seen a galvanized community of gamblers come together, buoyed by the opportunity to help each other beat the ‘books each and every night. It’s a community spirit that Kenny says has been completely organic in its evolution.

“Watching complete strangers become legitimate friends that interact daily and genuinely care for one another has been one of the most rewarding experiences of my life, especially during a year when there wasn’t a whole lot to feel positive about,” he said.

“Everyone just wants to see everyone succeed; whether it’s in gambling, in their careers, or in their relationships”

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Kenny, who is also part of a radio show in the Philly area on Fox Sports which is devoted to gambling, says a main source of his research for bets on player props is the NBA website as well as StatMuse, which enables bettors to create search terms and get insights based upon specific conditions.

In addition to those tools, during games McAndress has done away with the ESPN box scores that he originally followed when hitting his first big parlay, instead using a new tool created by two members of the #MoonieGang called Prop Tracker. "It's the single best app for tracking multiple player prop plays," he said. "I just hope they don't forget about us after one of the sportsbooks buys their incredible app for a gazillion dollars."

With sports betting blowing up across the country, and only due to get bigger as more states legalize it, Kenny says new time gamblers need to ask themselves what they’re getting into it for - for fun or to try and actually make money - and to set your expectations accordingly.

“If you’re someone who wants to get involved more deeply, at the outset, set your limits and your goals - both long-term and short-term,” he said. “Track everything. Poke holes in your research and constantly refine it. And most importantly, take a break the second it’s no longer fun.”

You can follow Kenny on Twitter @kiiLkenny, or catch him streaming on his Twitch channel.



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