When Kobe Bryant Honoured A Bet With The ‘Entourage’ Lads
— Updated on 24 August 2021

When Kobe Bryant Honoured A Bet With The ‘Entourage’ Lads

— Updated on 24 August 2021
Garry Lu
WORDS BY
Garry Lu

In the wake of Kobe Bryant’s untimely and unfortunate passing, the impact of his legacy has been revealed in some unexpected places.

One such example includes a story of when Mamba bet on himself, which also involves both Kevin Connolly (E) and Jerry Ferrara (Turtle) during the production of an Entourage episode.

The year was 2005. HBO was filming at the Staples Centre for the first time. Bryant had sustained an injury in his right ankle during a game against the Cleveland Cavaliers. Naturally, he’d been sidelined a fair few weeks for recovery. But that did little to slow his competitive drive.

After the cast and crew were done with rehearsals, Bryant made his way towards Connolly and Ferrara in a “boot” with an interesting proposition. A gentlemen’s bet, if you will.

The stakes were $100 for every one-legged, left-handed shot that Bryant made. Meaning that both E and Turtle would have to pay Bryant for every successful shot, and vice versa for every shot missed.

“We’re all in shock,” says Connolly in a text to Ferrara.

“Uhhh, hell yeah we’re in.”

RELATED: Michael Jordan Reveals His Last Text Messages With Kobe Bryant

Bryant’s first shot bounced off the rim. A setback, for sure. Though true to his reputation, he refused to stay down and out. The stakes were upped: double or nothing. Bryant went for the second shot. Nothing but… rim. Again. Bounced off.

At this point in time, the Entourage lads were just happy to have met a living legend and went about their day, not even thinking about collecting their winnings. They soon made their exit to let the Los Angeles Lakers prep for that night’s game.

Connolly and Ferrara stayed to spectate. Halfway into the second quarter, they received an envelope from the big fella himself.

“A dude shows up and taps us on the shoulder and says, ‘From Kobe’… eight $100 bills. Chills.”

Check out the scrolling screen record below to read the original story as told between Connolly and Ferrara’s texts.

Garry Lu
WORDS by
After stretching his legs with companies such as The Motley Fool and the odd marketing agency, Garry joined Boss Hunting in 2019 as a fully-fledged Content Specialist. In 2021, he was promoted to News Editor. Garry proudly retains a blue belt in Brazilian Jiu-Jitsu, black bruises from Muay Thai, as well as a black belt in all things pop culture. Drop him a line at [email protected]