Our Cars: Tim Tompkins’ 1969 Cutlass Convertible

Tim Tompkins’ Cutlass is a highway to the past


Tim Tompkins’ first car was a 1974 Triumph TR6, which he says “was a wonderful car except when the Prince of Darkness (those troublesome Lucas electrical components) visited, which was all too often.” In fact, Tim once drove the last 50 miles of a trip with no lights – during a storm.

He bought the Triumph for $500 and spent a lot more to keep it on the road, but the two-seater never sat for long. Tim regularly drove the car from Chappaqua, N.Y., seven hours up the Taconic Parkway and through the Adirondacks, to St. Lawrence University in Canton, N.Y.  And he wasn’t deterred by snow, driving it year ’round. “Usually, I was joined by two passengers, one of whom had to squeeze onto the little shelf behind the seats,” he said. “Of course, I never shared the driving duties as that car was a blast to drive, especially with the top down.”

After working for the Supreme Court of New York and at law firms in Seattle and London, Tim joined Hagerty’s legal team – and it was only a matter of time before he purchased a classic and joined the fun.

Title: Executive VP Business Development, Corporate Legal Officer

Years at Hagerty: Seven

Car: 1969 Oldsmobile Cutlass S

Why a ’69 Cutlass? In high school, we had a 1972 Cutlass Supreme, and since we had nine in my family, we also had the necessary Custom Cruiser wagon. Each of my older brothers got to drive the Cutlass to school during his senior year after dropping off Dad at the train station. The Cutlass, unfortunately, couldn’t survive the three consecutive senior years of high school prior to mine, so I never got to drive it. When I saw that our friend, Charlie Kuhn (of Chicago Classic Cars), had a ’69 Cutlass for sale on his website, it was only a matter of time until I got my chance – and it’s a better year than the old family Cutlass I missed out on driving.

Repairs and modifications: I had a new transmission put in, plus a stereo to convince my kids to ride with me.

Hobby activities: I participate in the Hagerty Cruise and the Hagerty Family Car Show every year.

Favorite drives: I love driving along the Taconic Parkway (in New York’s Hudson Valley). Locally, it’s M-22 (a 116-mile stretch of highway along the shores of Lake Michigan through four counties in northwest Michigan).

Best moments: My best moments in the car are when I’m out enjoying a ride with my family (wife, Maureen, and children, Molly, 17, Nonie, 15, and Teague, 11), although the single most memorable moment was probably last summer. Hagerty put together a small show for members of the military and their families, and the Navy Blue Angels flight team was there for an air show. We got our photo taken with the car in front of one of the jets.

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