How Michael Jordan’s Atlantic City gambling trip paved the way for his first retirement

As a long-suffering Knicks fan, I’ve become almost immune to the losing. When you can rattle off the memorable defeats as quickly as you can recall historic moments in your own life — getting married, having kids — you know it’s been a lengthy, painful existence rooting for the Knicks.

And no series loss stings more than when the Knicks blew a 2-0 series lead in the 1993 conference finals, otherwise known as the series sandwiched around the greatest Michael Jordan gambling story of all-time.

The series is remembered by the block, strip, block, block defensive sequence on Charles Smith at the end of Game 5. But Michael Jordan’s gambling excursion to Atlantic City stole all the headlines. And more importantly, as “The Last Dance” indicated on Sunday night, Jordan’s quick trip to A.C. paved the way for his first retirement.

Jordan owned the Knicks. Let’s start there. His Bulls defeated Rick Pitino’s Knicks in the 1989 playoffs, swept John MacLeod’s troubled Knicks in the 1991 playoffs, and beat Pat Riley’s on-the-rise Knicks in 1992.

But New York’s 1993 collection of talent was the best the franchise had seen in 20 years. They won 60 games and had the best defense in the NBA, led by a mix of unheralded tough guys — Anthony Mason, John Starks — and one of the premiere players in the league, Patrick Ewing.

The Knicks soundly thumped Jordan’s Bulls in Game 1. Ewing scored 25 points and collected 17 rebounds; Starks hit five three-pointers and scored 25 points while he and Doc Rivers harassed the NBA’s scoring leader into woeful 10-of-27 shooting. Still, Knicks fans knew better than to get excited about one win; New York won Game 1 the year prior. In Chicago, no less! And they still lost in seven games as MJ hung 42 on them in the clincher. We knew how this story could go.

But nobody could have predicted what happened next: Michael Jordan decided on the team’s day off to head to nearby Atlantic City for a gambling excursion. The buttoned up New York Times headline blared: “Jordan’s Atlantic City Caper.”

After practice on Monday, he checked into Bally’s Grand at 5:07 that afternoon according to a hotel employee, checked out at 11:05 P.M., was seen in the casino as late as 2:30 A.M., returned to New York and was on the Garden court for a midmorning shootaround, 10 hours before Tuesday night’s game.

The tabloid media in Gotham went wild with reports of Jordan’s colossal losses, which surely were going to portend a series loss to the overdue Knicks. MJ reportedly blew $5,000 playing blackjack faster than you can say shot clock violation. Did he really stay until 2:30 in the morning, with a game just 17 hours later?

Jordan offered firm denials to his coach Phil Jackson and GM Jerry Krause, saying he was in his room by 1 am, not on a casino floor. Yet a funny thing happened in Game 2: Jordan looked mortal.

Sure, he scored a game-high 36 points, but he shot a woeful 12-of-32 and the Bulls lost to fall into a 2-0 deficit. Through two games, Doc Rivers and John Starks combined to play His Airness to a standstill.

This story was the perfect storm for the media and historians; less so for Jordan himself, particularly given recent history. A year earlier, in 1992, Jordan reportedly paid out $165,000 in golf debts over high-stakes games. Combine that with the crummy start against the Knicks and the bizarre Atlantic City jaunt, and the media got out its collective jump-to-conclusions mat: Did the most popular athlete on the planet have a gambling problem? Perhaps the gambling chatter was simply getting to Jordan? Was the media swarm taking a toll on the unstoppable Air Jordan? Could it cost the Bulls a 3-peat?

The Bulls bounced back in Game 3 with an easy 20-point win, but Jordan had his third straight pedestrian game, shooting just 3-of-18. After going 1-for-7 from deep in Game 2, he abandoned the three-ball and became a facilitator, tallying 11 assists.

The gambling storyline kept coming, though, reaching a fever pitch in the heat of the Eastern Conference finals. Jordan brought it on himself with his decision, of course, but to him, it was just a quick father-son outing to help him get refocused. If the media was going to make such a big deal about something seemingly so trivial, at least in Jordan’s mind, maybe he didn’t need all this anymore.

You can see it in Parts 5 and 6 of “The Last Dance” — a world-renowned role model and superstar athlete who’s over the scrutiny and the spotlight. As reporters peppered Jordan with questions, he boycotted them. In episode five of The Last Dance, you can almost see the look of disdain on his face: I’ve won two straight titles and you’re going question me over gambling for a few hours in Atlantic City? Who were these ink-stained wretches to question the NBA’s best player?

Of course, you know what that meant for Game 4: Vintage Jordan. The quintessential performance to rip the hearts out of Knicks fans and remind everyone the gambling was just for fun, basketball was everything. Jordan made the media forget the gambling excursion with a truly epic 54-point night that included six three-pointers. The Bulls won the game. The Knicks never won another game in the series.

But the damage was done. Jordan’s penchant for gambling was well known; now it was very public in the midst of a quest for a third straight title. If there was any doubt in Jordan’s mind about whether it was time to step away from the game leading into the 1993 playoffs — a consideration “The Last Dance” shows was very much on his mind — then the firestorm around his wagering gave him the answer he needed, especially as the flames grew larger and larger.

Next came the publicity-seeking individuals seeking to capitalize. Within weeks, an entertainment executive named Richard Esquinas wrote a book and distributed it to reporters on the eve of the Finals, saying that the 3-time MVP had to pay off a golf debt of $300,000 and once was in the hole $1.25 million.

The book alleges that their golf competition included putts that often were worth $100,000 and sometimes rose as high as $250,000.

And that seemingly was enough for Jordan. He ended his media boycott before the Finals against Charles Barkley and the Suns, telling his buddy Ahmad Rashad that he didn’t have a gambling problem.

“I just felt that it was unfair that I was being considered a criminal for doing something that is not illegal,” Jordan said on June 9, 1993. “Gambling is legal, betting is legal.”

With that off his chest, Jordan had arguably his greatest Finals ever, outdueling Barkley and knocking off Phoenix in six games. A few months later, in October 1993, he announced his first retirement. Nothing left to prove in the NBA. Media is obsessed with me over this gambling stuff. Who needs it?

Really, it’s too bad. Maybe Jordan still retires without the Atlantic City brouhaha, of course. But maybe he comes back for the 1993-94 season if he finds another way to relax, or if the media doesn’t make such a big deal about it, or if he were a little more clandestine with his trip. Maybe we get to see MJ’s Bulls take on Hakeem’s Rockets. Maybe we get more of the duel between Jordan and the upstart Orlando Magic of Shaq and Penny.

With all of the noise surrounding him thanks to that one decision, though, there was no way he was going to come back. The Atlantic City sojourn in the midst of a heated Eastern Conference Finals vs. the rival Knicks was a tipping point in Jordan’s career. The national media sunk its hooks into what at the time was a tantalizing story: Rich, famous, and seemingly in need of a constant competition fix.

We openly laugh at that now, as the stigma against gambling has eroded. (My young kids, 1st and 3rd graders, are watching every episode of the Last Dance with me, are shocked at the references to cigarettes and cigars. Reverse stigma in effect on that one.) Yet, the Atlantic City excursion was one for the books. It combined some of my favorite things in sports in an arc fit for a documentary: The rise of the Knicks, Jordan going gambling, the media worked into a frenzy, the Knicks putting the screws to Jordan, then MJ exacting revenge, more gambling, and five months later, the best basketball player on planet Earth retiring.

All thanks to the biggest star in the world deciding to blow off some steam by playing cards.