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About Cadillac Carl

Carl Massaro (“Cadillac Carl”) began singing and playing guitar at age 12, starting with folk music such as Bob Dylan, Paul Simon, Lester, Flat, Jimmy Rogers, and the like.


In seventh grade, his junior high school held a “hootenanny” concert in the gym, and Carl sang several folk songs. As it turned out, the main act that day was Flatt and Scruggs. Carl went on to be a barroom crooner and ski bum, drifting from ski town to ski town, eventually ending up in Sun Valley, Idaho at the Crazy Horse saloon.


In 1975, Carl suffered a broken arm and leg after a bad ski accident. Destitute and unable to play guitar, he set up camp in a Triumph, ID mine tunnel to get well.


In 1977, the tour manager for Waylon Jennings heard Carl sing, and offered him a deal: He would bring Carl to Nashville if Carl picked up and delivered a horse for the bands' drummer. This brought Carl to Leiper's Fork, TN (with a mare in foal). He promptly moved into the mailroom at 1117 17th Ave. S. — Waylon Central — and the team got him a gig on the road with a band called the Goose Creek Symphony.


By the following Spring, Waylon and Willie were on top of the world, and every major writer came by the office at all hours of the day or night — Kris Krisoferson, Rodney Crowl, Johnny Cash and his daughter., Hank Jr., and David Allen Coe, to name a few.


Although this was an extraordinary time to be where he was, Carl observed one negative thing: “They all looked so poor, and I didn't want to be poor again.” So he got to work doing various construction jobs, writing, singing, and playing guitar when he could.


Another frequent face around the Jennings office was Lori, the “Outlaws’” secretary. After years of construction work, Carl moved back to Nashville in 1990 and married Lori. They made a great team in all aspects of life and started a real estate business together.


Determined to own a piece of Music Row, Carl and Lori began buying and remodeling building in the Music Row and Edgehill area. In 2000, they struck a deal with Vanderbilt to buy a dilapidated building that, at the time, was being used as a methadone treatment facility. Carl cleaned it up and began renting to nursing and medical students.


By 2008, with plenty of Music Row real estate to his name, Carl moved back to Idaho where he purchased his old home — the Triumph Mine. Carl has since focused on his singing and guitar playing. He says, “The story of the Triumph Mine and the company I bought is worth telling and if I can sing a few songs along the way, by God, I will.”

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