Monday, November 29, 2021

The Saltwater Cowboys Series Part Four: The Sheriff, the Smugglers, and the Saltwater Cowboys

The Sheriff, the Smugglers, and the Saltwater Cowboys

Marco Island has been very good to me. I have worked at what is now the JW Marriott on Marco Beach for over 40 years and back on that very bold Super Bowl Sunday in the mid-1980s, there was no exception. I was working.

My job at the time was to supervise the sailboats rentals, rides and lessons, organize the beach equipment, entertain and offer service to the hotel guests, and make sure everything was running smoothly on the waterfront at the Marriott beach.

At the time, I was single and living in the three-bedroom house on Fairlawn court. I shared the house with two friends that also worked at the hotel. Our combined rent was $600 a month. We were living the dream, working and playing in paradise.

Another aspect that made the dream lifestyle really fun was that 2 years earlier—with the help of dear friends—I was able to buy a 36-foot wooden sailboat that had been abandoned.

For the past 2 years, tons of work went into the boat to get her shipshape, and operational, and on the boldest day of Saltwater Cowboy smuggling ever, the old ketch—a sailboat with two masts—was at the Marco River Marina waiting to come back home to her dock and the canal on Fairlawn Court.

The Ketch had been out of the water to have the bottom cleaned and painted, and because she was a wooden boat, the sooner she got back in the water the better. Wooden boats can dry out, seams can open up, and as every professional knew, this was a bad scenario for any wooden boat that had been in the water for 29 years.

Because of this situation, and because the boat had been high and dry for the last few days, Chris Kenshiff from what is now Rose Marina called me at the Marriott on the super bowl smuggling Sunday and simply said, “Tom come and get your boat. It’s all ready and we put her back in the water this afternoon. She’s tied up at the floating dock by the travel lift and ready to go. We didn’t think it would be good for her to dry out another day. We’ll be closed after you get off work, but you can still pick up the boat. Come by Monday and pay the bill.”

I was happy to comply and after a fairly easy day of closing the beach—because most of the guests left early to watch the game—I was home at the house on Fairlawn Court just about the time the sun went down.

Mike and Keith were my roommates, and when I came home, they were watching the game on television. They didn’t look particularly interested in what was going on with the biggest day in football, so I threw out the question, “Hey, do you guys want to go with me to get the boat? She’s already in the water and ready to go,”

The boys looked at each other, nodded, and we were all out the door and headed over to the marina when the last of the sunset was all but over. When we climbed aboard the boat, it was completely dark. Soon we had the diesel started, the cabin and running lights on, and the mooring lines cast off soon after.

The old ketch was motoring through the water with little effort as the bottom paint was new and in only a few moments, we all saw something very out of place on the other side of the bay near O’Sheas—or what is now Pier 81.

Across the bay, in the channel, between the sandbar and the O’Sheas and Riverside docks, there were about ten smaller boats with each boat having what appeared to be about four or five persons on each boat.

The tropical darkness was inky black with only a few stars, but the water surrounding the little fleet of boats was greatly illuminated because it seemed every person on all of the smaller boats had a flashlight and was pointing their light beams into the water. 

Meanwhile, on the ketch we were curious, all in our twenties, ready for adventure, and even though this was not the direction of Fairlawn Court and home, I pushed the tiller over and we started for the light show unfolding on Factory Bay.

At first, it looked like maybe some kind of fishing was going on, or maybe something fishy, but when we came closer one of the boats with five big guys motored over and they didn’t care that they were making a wake.

When they pulled up alongside the ketch, the flashlights were no longer pointed at the water. The flashlights were pointed at us.

Every man on the small boat was armed. You could see the pistols in their holsters, and in the ambient light from five different flashlights searching our boat and our faces, we all could see their dark windbreakers with the big white letters: DEA

Before we could react, one of the Drug Enforcement Agents asked abruptly, “What are you guys doing here?”

“We’re taking our boat home from the marina,” I explained, “It just had some work done.”

“You’re taking it home in the dark?”

“Sure,” I answered, “I worked all day. I didn’t get off till after sunset.” 

Before any other explanation was asked for or given, the lead DEA agent turned his flashlight down toward the water as did the other agents, and to our vast surprise, there were seemingly hundreds of chunks of marijuana floating along the surface. The average chunk was the size of a basketball.

“What do you guys know about this?” the lead agent barked.

Before I could piece together an answer, my roommate Keith responded, “Wow, cool. I’ve never, ever, ever, seen that much pot.”

Mike and I quickly played along at the same time with the truth. We must have sounded like a chorus. “We don’t know anything about that!” we said together and pointed at the water.

“Okay fine,” the DEA agent seemed to relent. “But take your boat home now,” he insisted. “No more cruising around tonight and no scooping up any of this contraband.”

“Yes, sir,” Mike and I answered together.

After our encounter with the DEA, we did indeed cruise the ketch back to our dock and the canal on Fairlawn, and all along the way, one of the DEA boats followed us from behind. They came into the canal watching until we tied up, shut down the engine and the lights, then went into our house.

At the time, we had no idea what Frank, the Sheriff, and the rest of the Chief’s smugglers had been up to, but after the night that none of us will ever forget, I believe that Mike, Keith, and I just might be Saltwater Cowboys too.

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