For most, the “good old days” involve some variation of late nights in a bar with good friends, beers in hand. For Monroe County Sheriff’s Office Lieutenant Colonel Don Hiller, the glory days with good buddies involved on-water shootouts, international investigations, stacking bales of cocaine and millions of dollars in seized cash.
The turn of the calendar to May marks the end of four decades of service to the Keys for Hiller, who by this point has firsthand experience in just about every division of MCSO.
Looking up to his older brother in law enforcement since the age of 8, Hiller said he and his friends at Marathon High School – including current Sheriff Rick Ramsay – knew their paths were clear after graduation, beginning in 1985 as the agency’s youngest deputy.
“For my first 11 years as a cop, I was a volunteer firefighter too,” he said. “We’d work all day, be on call all night, and it was just the best time. We were adrenaline junkies.”
“It was a sergeant and two deputies working the Marathon zone, and it wasn’t uncommon for me to be working midnights by myself, doing traffic stops with a shotgun,” he said. “But Rick and the other deputies that were off had scanners – so if somebody was like ‘there’s a bar fight at the Monkey,’ and Don’s working by himself, they’d all come out.”
By his own admission, Hiller thought there was “zero chance” he’d live past 40 – or at least that’s what he told his wife, Teri, as his rise through MCSO took him through some of the most rewarding, but dangerous, sides of the agency.
“I was a pilot, I had a Harley, I’m diving, I’m on the SWAT team, I’m doing (drug) raids. There was just no way – something was going to happen,” he said. “I told her I was going out in a blaze. I made 40, and she said, ‘OK. Let’s see if you can make 41.’”
Over the course of an hour-long interview with the Weekly, Hiller’s stories always returned to his days of tracking down “cocaine cowboys” and the money that funded them during his first two decades with MCSO – and it was clear we’d barely scratched the surface of the stories he had to tell.
“Don is like family to me, and this Sheriff’s Office is a second family to him,” Ramsay said. “He was one of the best undercover narcotics agents I’ve ever seen. You would never think he’s a police officer – he has the gift of gab, and he’s calm, cool and collected. … Between all the stuff we’ve done together, I know every move he’s going to make, what his mind is thinking and vice versa.”
“We did a tough job, and I’d like to think we did it respectfully – it was just business, nothing personal,” Hiller said. “I think that’s how we’ve been able to coexist down here.”
Hiller logged extensive undercover work, and his time with the South Florida High Intensity Drug Trafficking Area took him around the globe, from mainland Florida to England and Monaco.
“That was on my birthday in ’96,” he said, handing over a photo of a camper van stacked to the ceiling with bales of cocaine. That seizure, he said, was an accidental discovery, and wasn’t even his largest; he’ll point to a single 2,800-kilo snag or a $50 million seizure in Costa Rica in the late ’90s as his hallmark grabs.
“We were shooting cowlings out, shooting engines out – it was just crazy days in a different world back then,” he said, recalling the days of doing his job with a six-shooter revolver. “It wasn’t so much violent, it was just ‘catch me if you can.’”
He recalled a night assisting a shorthanded customs and border protection with a marine patrol:
“We were sitting off Sombrero in a 39-foot boat. We got a call, and they said ‘You’re the closest unit. A Blackhawk helicopter just went down, and it’s 17 miles off the coast of Cuba.’ We looked at each other, put the hammer down, and got there at two o’clock in the morning.”
Today, Hiller has the pleasure of driving past “monuments,” of sorts, to his team’s success every day. Since the seized money couldn’t be used to pay MCSO salaries, then-Sheriff Rick Roth instead used the funds to buy equipment and buildings that would go on in service to the public – Trauma Star and its hangar, to name just two.
And while his days are, thankfully, a bit calmer than his stories from the ’80s and ’90s, he said he’s relished the chance to become a mentor and a well-rounded source of knowledge over the back nine of his career – and to see monumental transformations in training, equipment and collaboration in the process.
“I’ve worked with every captain, every lieutenant here – they all worked for me at one time because I’ve been here for so long,” he said. “Some of these kids coming up now, I worked with their dads, and I knew them when they came home from the hospital. Now they’re the future of the agency, so I hope they’re all going to take the reins and go to the next level.”
Hiller’s mark on Marathon isn’t limited to law enforcement. He’s also been a steady hand in leading the Pigeon Key Foundation as its board chairman, preserving and improving one of his family’s absolute favorite islands.
“There’s an ongoing joke that any time I need anything, I can call Don, and he’s always ‘got a guy,’” said the island’s executive director, Kelly McKinnon. “The thing is, Don’s always the guy. He doesn’t care about notoriety or getting credit – he just always tries to help everybody. You’d never know what his history is or his past is if you just had a standard interaction with him.”
“We don’t have a Hall of Fame at MCSO. But if we did, he would be in there,” said Ramsay. “It’s a loss for me, personally and professionally, the agency, and the community. The stable thing I’ve known in my entire career has been Don Hiller.”
“I’m going out as happy as the day I went in,” Hiller said.
The Keys Weekly staff wishes Lt. Col. Hiller a restful, well-deserved retirement. Enjoy the grill, the boat – and no more midnight text messages.
Photos contributed.
