Lines in the Sand: The Legendary Cocaine Caddie

Dear readers, while most golf stories from the 1980s involve persimmon woods and polyester pants, this tale isn't one of those and it is sure to blow you away (pun definitely intended). So fill a cup with your finest Colombian - coffee that is - and settle in for a tale about an underground network of caddies with profits that would make Gordon Gekko green with envy.

Like all great rise-and-fall stories, this one starts at the bottom – specifically, the bag room at a club we'll call Little Pelican Country Club. That's where Sonny Montana first made his mark, not as a criminal mastermind, but as a caddie with an almost supernatural ability to read greens. The members said he could spot a break that would make Ben Crenshaw second-guess himself. But what Montana really noticed was how many members disappeared into the locker room between nines and came out fired up and ready to play 36 more.

By 1983, while Miami was riding a wave of questionable prosperity that had turned the city into America's cocaine capital, Montana had figured out that Little Pelican’s membership was full of customers with no safe access to their favorite new pastime. The same skills that made him an elite caddie – discretion, attention to detail, and knowing exactly what the client needed – turned out to be perfectly suited for a different kind of service industry.

Montana's big break came during a member-guest when he was paired with a Colombian coffee baron who spent as much time in Miami as Medellín. As they discussed the grain of the greens, the conversation drifted to a different kind of agricultural business. Within weeks, Montana had something the snow-hungry members couldn't find at their other clubs: direct access to Medellín's finest product, with no middlemen cutting into quality or profits.

Montana's real genius wasn't just securing the supply - it was recognizing the perfect distribution network hiding in plain sight. While street dealers worried about turf wars and police raids, country club caddies moved freely among America's elite, invisible despite being right in front of everyone. The security gates and armed guards that kept the rough elements out were now working in Montana's favor, creating the safest marketplace imaginable. Why sling product on a street corner when you could make deals on the 7th tee, where the only shots you had to duck were from the double digit handicaps on the adjacent fairway?

By 1984, Montana saw opportunity outside the gates of Little Pelican and expanded to clubs nationwide to become what old-timers still refer to as 'The Bag Network' – a carefully curated team of caddies stretching from Palm Beach to Pebble Beach. Montana ran his operation smoother than a freshly rolled green. His caddies knew every nook and cranny of their respective clubs, every secret spot between the 7th and 8th holes where a quick transaction could take place. They communicated through a complex system of golf terminology that would have made the CIA proud. 'Reading the wind' wasn't about judging conditions, and 'checking the grain' had nothing to do with the grass.

By 1985, Montana's wealth became impossible to hide - not that he was trying. His fleet of Ferraris made the members' parking lot look like a Honda dealership, and his suits cost more than most regular caddies made in a year. But it was his behavior that really turned heads: correcting a banking CEO's arithmetic at the tip window, offering to "loan" a circuit court judge enough to cover his gambling debts, even suggesting to the grounds committee that the 15th bunker needed more "Colombian sand."

But it was his 30th birthday celebration that would prove to be his undoing. The same man who had built an empire on discretion decided to host Miami's party of the decade in Little Pelican's hallowed main dining room. Picture it, dear readers: The usually austere space transformed into something between a Versace showroom and a Miami nightclub - white roses everywhere, crystal champagne fountains, and of course the obligatory caged tiger on the terrace. The guest list was a who's who of 'who shouldn't be here' – nouveau riche caddies in silk suits, mysterious 'business associates' from Colombia, and even a few compromised members who'd lost their moral compass somewhere between the bag room and the Bolivian powder room.

Just as Montana mounted a table for a champagne toast, resplendent in a white linen suit, his carefully crafted facade crumbled faster than a member's handicap during an audit. FBI agents swarmed in from every entrance – including the assistant pro who'd been gathering evidence for months, the locker room attendant who'd been noting every suspicious interaction, and even a member who'd flipped on Montana after getting caught with a gram on his drive home, choosing to wear a wire rather than let his wife learn about his afternoon pick-me-ups.

As federal agents paraded him through his ruined party, the lead agent - who'd spent the last six months posing as the new assistant pro - allegedly leaned in close and said: "Say goodbye to the country club life, Montana. Your lie is unplayable."

These days at Little Pelican, even during the coldest South Florida winter, you won't find a trace of snow in sight, and the biggest powder concerns rest on the shoulders of the locker room attendant ensuring there’s enough in the bathroom for post-round foot relief. Like every match play hero who talks trash at the turn only to choke down the stretch, Montana's downfall came from forgetting the golden rule: the quieter you play it, the longer you stay in the game.

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When a rafter of wild turkeys turned a 1960’s club championship into a game of survival, some members wanted to serve them for Thanksgiving dinner while others just wanted to serve them a less violent eviction notice. A holiday tale that gives new meaning to 'shotgun start.'

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