Dermott Bottoms Is Blacktip Island’s First Private Eye


Dermott Bottoms has opened a private investigative service on Blacktip Island, the first of its kind on the small Caribbean island. (photo courtesy of Gary Halvorson, Oregon State Archives)

Blacktip Islanders seeking help with unsolved crimes and hard-to-find information have a new champion as of Wednesday, when long-time resident Dermott Bottoms received his private investigator’s license from the Caribbean Association of Research Professionals.

“Lots of happenings on Blacktip Island, not all of ‘em good,” Bottoms said. “What people need is someone unofficial to help when the police won’t.

“Grew up dreaming of being an inquiry agent, see,” Bottoms said. “‘Dermott Bottoms, P.I.,’ y’know? And I’m out and about anyway, hearing things and seeing things. Thought to myself, ‘all right, then, why not mix business and pleasure?’”

Many residents welcomed the new investigative service.

“This’ll keep Dermott occupied, and I don’t suppose he can do too much damage,” said retiree Frank Maples. “Of course, it’s hard to go undercover or disguise yourself when you’re 6’6” and 300 pounds. And blind drunk by noon.

“Cyber surveillance could be his wheelhouse,” Maples said. “If he can learn how to switch on a computer. Last week he strapped on a hidden camera, but got the ‘on’ and ‘off’ reversed and ended up with video of himself in the Eagle Ray Cove toilet. The clients weren’t happy.”

Other locals were more skeptical.

“We need a PI on Blacktip?” the former-Reverend Jerrod Ephesians said. “There’s the Ballyhoo happy hour for information, and a policeman for crimes. All this does is get Dermott’s talking like Humphrey Bogart. It was funny at first, but now it’s just annoying.”

Others concurred.

“The last thing this island needs is another dick, private or otherwise,” divemaster Alison Diesel said. “It’s creepy, him following me around, peeking my the windows at night. After I hired him to find my bike.

“He should get his nose punched, sticking it in other peoples’ business,” Diesel said. “Only he’s, well, Dermott, and no one’s that suicidal.”

Island authorities downplayed the gumshoe’s impact.

“As long as Dermott’s not driving a moving vehicle, I don’t care,” said Island Police Constable Rafe Marquette. “I’m not sure he’ll get many cases, anyway. He found a lost bike, but the island’s only a mile wide.

“True, I’ve arrested him once for trespassing. And twice for stalking,” Marquette said. “But the next morning I just turn him loose after he sleeps it off.

Bottoms admits he’s still learning the finer points of his new profession.

“One big case already, but that dame, she played me, y’know,” he said. “Shoulda seen it coming, that double-, triple-cross. But I’m a sucker for a big brunette. Won’t happen again, though. Not often, anyway.

“I’m not Sam Spade, but I am Blacktip,” Bottoms said. “My motto’s: ‘Dermott gets to the bottom of everything.’ And if people don’t have money, they can pay in beer.”

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