Jake Skorheim once walked away from becoming a PI. Here’s why.

Following the announcement that iconic photographer Greg Gilbert is retiring after 56 years with The Seattle Times, KIRO Nights host Jake Skorheim thought back to the myriad of odd jobs he worked after graduating high school before becoming a radio host.

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“For a while there, I was a photographer for a private eye,” Skorheim said on KIRO Nights. “Now the way that I got into that job was, in my younger years when I was in my late teens during the summer, after I graduated from high school, I was playing a lot of poker at the time as young men want to do. And I was playing poker with these guys that were a little bit older, they were probably in their 50s or something.

“Now you might ask yourself, why are these 50-year-old guys hosting these young 18-year-olds? You can come to your own assumptions on that,” Skorheim added. “Probably they realized we were just easy marks and we gave him our money. But 18-year-olds don’t have much money. So I lose all my money to these guys one day and one of them says to me, ‘Hey, if you want to make that money back, I know a guy who is downtown. He’s a private eye and he is always looking for help. You should give him a call.'”

Skorheim was also working for the Seattle SuperSonics during this time as a ball boy, and the idea of working alongside a private investigator was too much to pass up.

“It’s like it was going to be the prime of my life at 18, I’m so excited. I was so happy,” Skorheim said. “I drive down there and I’m a little bit scared because it was in the area of Pioneer Square (in Seattle) that his building was in. This old, old old building. Looked straight out of a ‘Dick Tracy’ novel. Had my parents known where I was going, they never would have let me go. Absolutely not. They would have stopped me instantly because it was not a safe looking area.”

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The private investigator Skorheim was about to work alongside was Pascal Calabrese, also known by the name ‘Paddy.’ He previously ran Sherlock Holmes’ Cafe and Precinct House in Spokane. That business closed in 1981 after the revelation that the chief of the intelligence unit of the Spokane Police Department had invested $50,000 as a secret partner, The Buffalo News noted in 2005.

“So I’m sitting across from this guy named Paddy Calabrese and he puts his leg up on the desk. He’s sitting in front of one of those big circle windows behind him, looking across at me and he goes, ‘so I hear you want to make some money?'” Skorheim said. “I said, ‘Yes sir, I’d love to make some money.'”

The job Calabrese had for Skorheim was to follow people around and take their pictures — much like a private investigator would.

“He gives me a manila envelope, and just in the envelope is a piece of paper with a name on it, an address, a description written with a typewriter of a lady and where I would need to go and a disposable camera,” Skorheim said. “He told me, ‘We’re being paid to follow her. You need to follow her for four hours. Her husband thinks she’s she’s cheating on her.’ He thinks she’s cheating on her with her cousin, which is a weird thing. So that’s my entry into this weird world.”

Calabrese was willing to pay $50 for four hours of work, which was “fantastic money” for 18-year-old Skorheim.

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“So I go out to this lady’s house, and I practice a little bit on the way out because I think to myself, if I’m going to be following this lady around, there’s some spy craft that’s going to be involved in this,” Skorheim said. “So, I watched some spy movies and I’m thinking about how to blend in with the background, and you’re following her in the car and all that stuff.

“I go to a park in front of her house in Bellevue, and I’m sitting in my truck that does not fit in well in Bellevue at all. That was the first mistake,” Skorheim continued. “She comes out of her house and I start snapping pictures and I realized, I’ve already taken 12 shots on this thing. I got four hours left to go and I don’t have another camera. If I pull over to get a camera, I’m going to lose her and I’m going to lose this case right away. So she’s basically being followed by a child version of the Pink Panther or Mr. Magoo or just an idiot.”

But Skorheim continued to follow the woman around town running errands, snapping pictures the entire time. After spying on a meeting between her and another person, he came to the conclusion that her husband was just insecure.

“They were having a fight and he thought to himself, ‘She must be cheating on me,”’ Skorheim said. “Now I’m going to pay this guy to follow her around. But I found nothing on her.”

Skorheim continued working with Calabrese for six weeks, even roping a friend into picking up some cases. But he could never shake off the feeling of being a sleaze and eventually got too uncomfortable with the job as a whole.

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“A few years go by, and I think nothing more of this job other than it being a delightful anecdote to tell at parties that I was once a private eye,” Skorheim said. “Then a few years ago, I’m wondering, now that the internet is a thing, I’m going to look this guy up and see whatever happened to him. So I find this article from 1990 on him and he’s in The Seattle Times.”

The article’s headline: “Private Eye Had To Go Public, And Didn’t Especially Like It“. In the 33-year-old piece, Rick Anderson detailed that Skorheim’s old boss was the first Mafia informant to be given a new identity by the federal government. Calabrese was originally convicted of an armed robbery of the treasurer’s office in Buffalo City Hall in the 1960s before he testified against major Mafia figures, including Buffalo Mafia boss Frederico Randaccio, who was sentenced to 20 years for conspiracy.

He went into hiding under an assumed name, Pascal Calabrese, after testifying against the Buffalo Mafia He lived in Reno, Nevada, for five years, working as a security consultant for gambling casinos. There he began his work as a private investigator, consorting with criminals as an undercover agent for the government.

“And when I first meet him, he had this suspicious leg injury,” Skorheim said. “It was a weird spot to be in. Anyway, that’s how I was a private eye, but he was a great family man and his family loved him. He was a really cool guy.”

Calabrese has been credited with playing a major role in cracking a vice and gambling ring on the Alaska pipeline when he was working as a freelance undercover agent during the 1970s. Then, while working with U.S. and Canadian authorities, he infiltrated a counterfeit-money ring, leading to the arrest of six Mafia figures and the seizure of $1.2 million in bogus money in Canada.

Calabrese died from a heart attack at the age of 66.

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