The end of the year felt like it was on fast-forward, with Los Angeles racing toward the millennium's first finish line in a blur of holiday buzz and industry hustle. For Leon Donaldson, time seemed to compress even further.
The Princess Diaries was in its final, frantic prep phase. The sets were ready—Genovia's opulent yet cozy palace and Mia's humble, warm San Francisco home meticulously built in the studio, waiting for the cast to bring them to life. Casting was locked in, with the main actors wrapping up intensive etiquette, vocal, and script read-through training, all in peak form. Director Garry Marshall was champing at the bit, and the whole crew was like a finely tuned machine, fueled up and ready to roar into action on January 5, 2000, for a three-month shoot.
Amid this chaos, Adriana Lima's presence was like a burst of fiery South American sunshine, cutting through Leon's packed schedule. The Brazilian supermodel, fresh off her Victoria's Secret show, was a rising star, swamped with cross-industry promos and commercial gigs. But whenever she had a free moment, she'd pop into Leon's orbit, leading to a few passionate, thrilling nights—spicy footnotes to his relentless workload.
In contrast, Carmen Kass kept things cool and measured, like her personality. Their few phone calls were brief—polite check-ins with a hint of curiosity before she'd cite work and hang up, maintaining a faint connection rather than chasing anything immediate.
Anne, meanwhile, only managed a few short meetups, her parents sticking around until after New Year's.
Leonardo DiCaprio, on the other hand, was visibly bouncing back. The dark cloud from The Beach was lifting, replaced by new purpose and energy. He was hustling hard for Catch Me If You Can and had rediscovered his love for basketball.
On December 3, he dragged Tobey Maguire and Leon to the Staples Center for a high-stakes Lakers vs. Portland Trail Blazers game. On the way, Leonardo and Tobey geeked out over the teams' lineups and key matchups. Leon, listening quietly, felt fragments of a past-life memory click into place—this was the game where Kobe Bryant, fresh off an injury, staged a legendary fourth-quarter comeback. It was a nail-biter, but the Lakers pulled it off, with Kobe's explosion sealing the deal.
A wild idea hit him. He needed cash. The Princess Diaries budget was manageable, but he'd sunk a lot into it personally, and upcoming projects like Catch Me If You Can and Girl with a Pearl Earring would need funding too. Final Destination's box office profits were trickling in, but his ambitious plans demanded more liquidity.
Betting on the game? It sounded risky, borderline insane. But with his future knowledge, this wasn't a gamble—it was a calculated "investment."
"Leo, Tobey, you guys ever place a little bet on games like this?" Leon asked casually.
"Sometimes, just for fun," Leonardo replied, glancing back with a grin. "Why, you interested? Tonight's tough, though—Portland's got Pippen, they're solid. Lakers are coming off Kobe's injury, so it's a wild card. Odds are probably decent, but it's risky."
"Just curious," Leon said, smiling, his mind already made up.
At the arena, while Leonardo and Tobey chatted with friends, Leon slipped away to connect with a trusted private betting contact Leonardo had mentioned. After a quick talk, he confirmed the odds: with Shaq's emotional volatility and Kobe's uncertain return, the Lakers were underdogs at 3-to-1.
Leon didn't hesitate. He calculated his available liquid funds—$1.5 million, the max he could risk without derailing his plans. With a calm that surprised even himself, he said into the phone, "$1.5 million on the Lakers to win."
There was a pause on the other end, the amount clearly catching them off guard, but they quickly confirmed the bet. Hanging up, Leon felt his palms sweat and his heart race. $1.5 million was nearly all his discretionary cash. Win, and his funds would balloon; lose, and his plans would take a hit, though he'd survive.
Back at his seat, Leonardo and Tobey didn't notice the massive move he'd just made. The game kicked off, and as Leon's memory—and Leonardo's prediction—suggested, it was a slog. Pippen, still a force, carved up the Lakers' defense with veteran savvy, and Portland held the lead most of the game. At halftime, the Lakers trailed by a few points, and the mood was grim.
Leonardo and Tobey dissected the game, skeptical about a comeback. Leon stayed quiet, sipping his drink, torn between confidence in his memory and a nagging anxiety. Knowing the outcome was one thing; watching it unfold was another.
The second half took a wild turn. Shaq, after a controversial call, lost it, yelling at the refs and picking up two technicals—ejected! The Staples Center erupted in boos and gasps. Down 70-77 without their star center, the Lakers looked doomed.
The jumbotron caught Leonardo, Tobey, and Leon in the crowd—Leonardo and Tobey visibly stunned, Leon playing shocked but inwardly screaming, This is it! Their faces on the big screen drew a mix of laughs and groans from the crowd.
"Shaq, you idiot!" Tobey groaned, head in hands. "We're done for!"
Leonardo slumped, deflated. But Leon's eyes were glued to the No. 8 jersey. He knew what was coming.
In the fourth quarter, Kobe Bryant's demeanor shifted. The hesitation and rust from earlier vanished, replaced by a cold, almost ruthless focus. He drained a tough mid-range jumper, then stole the ball for a fast-break score. A pull-up three followed—bang! The basket must've looked like an ocean to him. Nine straight points! Kobe single-handedly unleashed a jaw-dropping run, flipping the game's momentum.
The Staples Center went berserk, the roar nearly lifting the roof. Leonardo and Tobey shot out of their seats, screaming, barely believing their eyes. Leon clenched his fists, a rush of joy and relief flooding him. They'd won—not just the game, but his bet. $1.5 million was now $6 million.
The final score: Lakers 93, Trail Blazers 80. As the buzzer sounded, Leon kept his cool, a restrained smile masking his inner triumph. Leonardo, still hyped, pulled him and Tobey to the locker room with his connections to congratulate the team.
The locker room was electric. Shaq, despite his ejection, was all grins. Kobe, the night's hero, glistened with sweat, exhaustion, and satisfaction.
"Kobe, you're a damn legend!" Leonardo said, throwing him a bear hug.
"Unreal, man!" Tobey added, slapping his shoulder.
Leon stepped up, offering a handshake. "Hell of a game, Mr. Bryant. Your grit and skill under pressure were something else."
Kobe shook his hand, nodding. "Thanks, Mr. Donaldson."
Shaq bounded over, oblivious to his earlier blunder. "Yo, Leo! Your crew's alright! Tonight was wild! I'll hook you up with prime tickets next time!"
Leaving the buzzing arena and piling into the car, Leonardo was still riding the high. "God, did you see that? Kobe! The guy's a hero! I'll be talking about this comeback for a year!"
Tobey nodded, dazed. "Like a dream."
Leon gazed out at the passing city lights, feeling lighter than ever. The thrill of witnessing the iconic game was only part of it. That $6 million windfall would ease his cash flow crunch, fueling The Princess Diaries, Catch Me If You Can, and Girl with a Pearl Earring.
"Yeah," Leon said with a knowing smile, "like a dream."