Orrie Simko: An Old Soul in the Realm of Full Classics

It is generally accepted that you gravitate toward the cars that were new as you grew up. So, logically, 35-year-old Orrie Simko should be digging on cars of the early ’90s. Not a chance. Simko is an old soul; his vehicles of choice come from 1910 to the 1930s. Some might sneak into the ’50s, but that’s pushing it. He has had a love affair with these early cars since he was a little kid.

Where Simko grew up in Collinsville, Connecticut, there were many cars from the prewar era, so he was exposed to them more than others. Even if an exotic from the ’60s or ’70s passed him by, it was still the majestic and stately automobiles of the early part of the 20th century that attracted him. 

“It was the lifestyle that I dreamed about,” he says. “I would see a beautiful ‘Painted Lady’ home [of the Queen Anne era] and fantasize about a Locomobile or ’29 Cadillac that might have been parked in the garage. It was a world I aspired to.”

The lines of those grand old cars, their history, and why they existed in the first place have always intrigued Simko.

“I don’t know why I’ve always been captivated by Brass Era cars,” Simko says. “I remember a TV show I saw as a little kid with big cars like Thomas Flyers and a really early Rolls-Royce Ghost driving along the ocean. There was just something about the brass steering column and the big wooden wheels. The presence and elegance of these big Edwardian machines making exhilarating sounds that just sucked me in.”

Of course, there were books, too. Simko frequented the library, checking out every book he could find about early cars. His parents and younger brother were not into cars but would hit all the local car shows for his benefit. When the family went on vacation, his parents made a point of searching out a car museum for their young son. The now-defunct Wells Auto Museum in Maine was always a highlight. 

He used to pass by a shop in Collinsville where there was always a unique car, like a Packard or a Lasalle, sitting out front. The shop was wide open, so one day, Simko sat on a milk crate and waited for the owner to return. That’s how, at 16, he started toiling away there for a crotchety old collector.

“The owner of all the cars was a nasty SOB. All I was to him was cheap labor, and I labored a lot. But he had dozens of cars stashed away, which was like Aladdins’ cave for me. The guy was a taskmaster who screamed and cursed at me nonstop, but I endured for the love of the cars and occasionally got to drive one of them.” 

In the process, Simko learned the craft of being a prewar dealer. “I also learned about the type of dealer I didn’t want to be.”

Around the same time, Orrie met Tim Kelly by chance at the Greenwich Concours. Kelly would greatly influence his life. He was the person who got Simko behind the wheel of the Brass Era cars he so loved but had no access to. Kelly also gave Simko an appreciation for unrestored original cars and Springfield Rolls-Royces. Kelly’s family wasn’t all that interested in his foolishness, so he would take Simko along to events all over the country. The truck pulling the trailer would become a classroom, and Simko welcomed the shared knowledge.

Kelly’s only request for his tutelage was that Simko promise to help fire that interest in others. “Tim wanted me to get another generation interested in the hobby,” Simko says. “I promised when I had the chance, I would share my cars with young kids. That chance happened sooner than I expected, and I have kept that promise to my dear friend.”

Simko went off to college in Boston in 2007 to study business, with a focus on entrepreneurship. It was during this time he discovered a “modern” car he wouldn’t mind driving. 

“I was on my bike and came upon a 9000-square-foot derelict mansion with a ’74 Cadillac Eldorado convertible sitting out front. It was like something out of Grey Gardens. An alcoholic mother and daughter were living there. They said they had misplaced the keys. I thought the mechanic who worked on the car wanted it for himself and had hidden the keys from them. But I called in a locksmith, paid them, and the Caddy became my college transportation.”

By 2011, straight out of college, Simko was offered a job as an electrical estimator for construction projects. He had grown up in the construction world and also interned in the role, so it was an easy fit though not necessarily a dream job. On the weekends, he played with cars as a hobby. 

One day, he got a phone call regarding a Craigslist ad for a ’29 Packard and a ’29 Rolls-Royce. He took a drive to look the cars over. “I was thinking maybe I could get a free Packard if I sold off the Rolls, or vice versa.” In the end, he passed on the pair. They were not up to his standards. But he did pick up a six-cylinder 1956 S1 Bentley from someone else. He got it running, had fun with it for a while, and sold it on. He found that Bentleys were easy to work on, so he did this several times. 

Another thing Simko learned was that his great love of these cars was not shared by the young ladies of his generation. “Early Bentleys were not chick magnets,” he says. “I had to get by on my charm if I wanted them to take a ride with me.”

In January 2014, he was introduced to Robb Burt of Sports & Specialist Cars, and he leapt at the opportunity to leave the electrical industry. Simko moved to New Jersey and took a job with the company selling Morgans, Aston Martins, and Lotuses. Among the new machines, however, hidden away in the back, was a 1929 Lincoln Phaeton. Simko was the only one who knew how to start it, so he got to drive it. “You just can’t get into one of these cars like you’d get into a new Lotus and drive it well,” he says. “There is a skill you have to learn. You have to train yourself to live with it.” 

During this time he also interned at Honda of Princeton, where Burt was a major owner. He quickly discovered he hated it. “Man, I couldn’t stand selling modern cars. It was like selling washing machines. There was no soul in those cars.”

When the time came for Sports & Specialist to close its doors, Simko was offered a position at the Honda dealership. “I wrote a very nice letter and politely declined. But it was another learning experience.”

He interviewed for a job with RM Sotheby’s but that didn’t materialize, so he started searching elsewhere. In late 2014, Simko was aggressively courted for a job at Philadelphia-based exotic dealership LBI Limited. The numbers were good, and he had a girlfriend in Pennsylvania, so he jumped in. The company dealt almost exclusively with modern cars, but Simko took care of a few old cars, like MGs and Pagoda Mercedes. But it still was not the right fit. 

“LBI and I had very different philosophies on business and how it should be conducted,” he says. “It wasn’t my cup of tea.” But in May 2015, Simko had the opportunity to take over a dealer’s license, and he went out on his own. 

He was back in Connecticut, working away for the crotchety collector on the side and learning more about the old car world and what being a dealer in that market was like. He continued building his connections and his reputation, letting the old-timers know a young guy could be trusted—and that he knew his stuff. He chased down leads with the best of them, aggressively searching out barn finds, working his magic, and saving them from being scrapped or being turned into hot rods.

As a dealer, Simko is picky about the cars he represents. Before he puts his name on one, he thoroughly vets the car and its owner. He wants every transaction to be smooth and enjoyable. His connection with his clients doesn’t stop with a sale, either. He facilitated the sale of the PBX, a Fiat/Crosley-based historical H Mod race car from the 1950s with a long history of wins in the Northeast. Even after the deal was done, he represented the PBX at the Greenwich Concours so its new owner could continue to race at Lime Rock the same weekend.

He also does all he can to convey to his generation the enjoyment of being around and driving early cars. He’ll recommend people start with an old MG, like a TD, and hope that will lead them to an old Ford or a Bentley. It’s like introducing someone to Eric Clapton, and then they find out about Muddy Waters. But with the cars, they have to learn how to use a clutch, let alone how to advance or retard the spark.

His personal car is a 1922 Sunbeam 24/60 with a custom aluminum body by Brewster. It was previously owned by early collector D. Cameron Peck, racer and Sebring 12-Hour founder Alec Ullman, and collector Charlie LeMaitre, so Simko is in good company. It’s a big car with a big engine, very fast, with two-wheel brakes and no Bluetooth.

The passion and love for these big old cars are deeply ingrained in him. The feeling is infectious, and the old-timers are drawn to his enthusiasm, which makes it easy to create connections that help make his business grow.

The Lincoln owner from the Simko’s Sports & Specialist period remembered him and believed in him, for instance. “He entrusted me with selling an exceptional car of his, a 1929 Packard 645 Dual Cowl semi-custom by Dietrich. A real one, not a rebody. It was the first of many notable cars I’ve sold, and a real feather in my cap.”

When Louis Vuitton needed someone to pilot the company’s freshly restored 1929 Citroën delivery truck to various venues around Manhattan, it was Simko who got the call. But even before he could drive it, he had to get it running in the New Jersey logistics facility where it had been sitting since restoration. Of course, he was up to the task.

He’s been at this for a while now, and with his many connections in the hobby, Simko can serve clients who want to fly under the radar—those who don’t want to deal with tire kickers or have their machines on every site on the Internet. He’s able to curate just the right buyer for a special car without bringing it out on the public market.

Orrie Simko is old school. He believes in honesty, integrity, and reputation. He also believes in print ads in Hemmings. Still, he is just 21st-century enough to have a website.

He’s a young guy out of time, but very much part of his time.

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