Donald Osborne Interview

Story by Sean Smith
Lead photo by Sean Smith
Photos below courtesy Donald Osborne

Just a kid in Manhattan without a car

When you are growing up in Manhattan and Queens, your family doesn’t need a car to get around. This was the plight of Donald Osborne; not till the age of 12 did his family own an automobile.

That didn’t stop Donald’s older brothers from reading Road & Track and AutoWeek. Donald, already a voracious reader, would get a hold of them and consume everything between the covers.

His brothers took him to his first auto show in 1964 at the Coliseum in New York City, and he just went crazy. Even at that tender age of seven his tastes were already set; he gravitated towards the Citroen DS, the Lancias, Abarths and other foreign exotics. He even fantasized as to how to pronounce the names, as he had never heard them, only read them.

Donald also found the magical Polks Hobby Shop in Manhattan. Whether it was in a life or death dice on the slot car track on the top floor of Polks, or building a model of a Jim Clark F1 Lotus, Donald found a hobby which fueled his imagination and dreams. He and his brothers began to create their own automobile lines and hand drew the sales catalogs. His brother’s was the “Machel,” Donald’s was the “Vulcan.” He created a full line of cars, family cars, sports cars, even vans.

The way the love of art and the love of cars come together is in automotive design. Donald applied and was accepted to Pratt Institute for industrial design, after having graduated from high school at the age of 16, with a major in art. But another love raised its head.

Singing Carmina Burana with the New York Philharmonic

In addition to his car hobby, Donald had been singing in choruses. At 12(!) he had his first professional engagement, singing in the chorus of the New York Philharmonic, performing Carl Orff’s “Carmina Burana.” He had a childhood friend who sang with the New York City Opera so he got free tickets. So instead of paying a buck fifty to go to the movies Donald went to the opera!

As he was about to graduate, there was a scholarship competition sponsored by the New York Daily News. The winner would receive a $500.00 scholarship, a story in the paper and sing in a concert. So he jumped in feet first. When the judges asked “Is there anyone left to sing?” Donald announced “Sure I’ll sing!” He sang and he won. A love of art, theatre, history and music all came together, so Donald forgot about the Pratt and headed off to college as a 16-year-old opera major and graduated with a BA in opera from the Hartt College of Music in West Hartford, CT, in 1977. He worked his way through college, with jobs at the school in the instrument room & library, as a Holiday Inn reservations center operator, and singing in the Extra Chorus at the Metropolitan Opera.

After college, Donald still singing with the Metropolitan Opera chorus. It was a great break but wouldn’t pay the bills. This sage advice was imparted to Donald: “If you are going into the arts you are going to have to find a way to support yourself before you make it big.” A love for cars seemed to lead to a job at a car dealership. After a few false leads, he found a Buick dealer in Hartford, CT that was looking for salesmen, no experience needed, they would train. His career with Buick lasted all of four hours. He went to the introduction then he went to the general manager of the dealership and told him in no uncertain terms “This is NOT for me, I will hate cars if I do this! Thank you very much.”

Next stop, Macy’s. He went through the executive training program and became a junior executive, all the while he was still singing in the Extra Chorus of the Metropolitan Opera. He was doing fifty hours a week as an exec and sneaking out at lunch to rehearse at the Met. At the end of the season Osborne went to the Chorus Master and confessed he could no longer sing as he was too tied up in the 9 to 5.

“You’re going to do WHAT?”

The Chorus Master was firm, and probably right; as a talented young black man with his foot in the door at the Metropolitan Opera, this might not be the best time to walk away. Business could wait a career in music wouldn’t. Donald listened, quit Macy’s, sold his car, bought a piano and pursued his singing, while still partnering in some other businesses in NYC. He went out on the road and toured the country for eight years and came back to the Metropolitan Opera as a soloist, making his debut in the 1984-85 season.

After a few years one thing became painfully clear, Donald loved to sing, but hated the business of music. The more success came his way the less he liked it. And music was such a joy to Osborne. It was just like those Buicks. He didn’t want to come to hate music. So he retired from his singing career.

Back to Macy’s. Donald lent his talents to many jobs throughout the company. He wrote, directed produced and starred in the promotional videos. This led to another job with a company called Focus Networks creating satellite broadcasts for retailers. That in turn led to Osborne opening his own marketing and communications company, it was then bought out by Burson Marsteller, a global public relations and communications firm.

Finally, a career with cars

Another marketing company was then created with a partner, but Donald’s first love was still cars, so he became an Accredited Senior Appraiser in personal property with a specialty in automotive by the American Society of Appraisers and started his business, Automotive Valuation Services, in 2004.

Donald describes himself and acts as a consultant. He will become the eyes of his client when looking over an automobile that may be thousands of miles away, but he knows the criteria and with his knowledge and expertise he can say this is the car for you and his clients will pull the trigger. Osborne is often referred to as the guy who tells people what cars to buy. He counters with “I’m more often the guy who tells people what cars NOT to buy.”

A voice of reason

Donald becomes the head to the buyer’s heart. As with machines in this stratosphere, it is often emotional, so Donald is the voice of reason. He listens to all the criteria and helps guide the buyer to the right car. He helps educate the buyer on how to choose the right machine that will give them the most joy or the best possible return.

In Donald’s mind someone can have a collection of automobiles that they have no emotional connection to, but why? He would rather there be great love than pure avarice.

Osborne equates his work to that of a great interior designer or architect. It’s not his tastes that are important, it’s the tastes, enthusiasms and passions of his clients that he is attempting to satisfy. He discovers what his client is searching for. Do they want to go on rallies, do they want to show a car at regional events, do they want to show a car on the international concours scene, or do they want to possess the most perfect example of a specific marque. He can then search out the car to fit those needs.

Donald and Jay Leno

Then, television beckoned. There was need for a host replacement on “What’s My Car Worth.” (2009) The network initially went to Wayne Carini, but he was tied up with his own show “Chasing Classic Cars” that had come about because of a New York Times article that Donald had written about Wayne and his Hudson Italia. Carini suggested Donald as a perfect match for Keith Martin. However, after a while the network decided it was in search of a younger demographic. It was perceived that Osborne was too sophisticated for the audience they were trying to reach.

At the same time Jay Leno was in conversations with NBC about his TV project. Donald had done an episode of the web based show with his Lancia Fulvia Sport and there was a great deal of mail and comments about the great chemistry of the pair. He asked Donald to be part of the pilot he was going to do. They did a show with Jay and Donald on the field at the Quail. The subject: what people should think about before buying a car. The result was that he was asked to join the “Jay Leno’s Garage” show for its series debut in 2015, and still appears with “Assess & Caress with Donald Osborne.”

Along the way, he became a monthly columnist in Sports Car Market magazine and has been published in the New York Times, Art & Antiques, The Wall Street Journal Online, Octane and other publications. Then there is judging, a natural extension of the appraisal process. What is valued in a good judge is their knowledge and observation; the perfect judges are often restoration experts and appraisers. From his years of experience at auctions, Osborne had trained his eye so he knows what to look for. That discerning eye is put to the test at the Amelia Island Concours, the Concorso d’Eleganza in Kyoto, Japan, and he is now the Chairman of the Concours d’Elegance at the Audrain’s Concours and Motor Week in Newport, RI.

The Italian line

Donald has eyes for the coachbuilt machines of Italy. This goes back to his love of art. Having artisans take a conveyance and elevate it to rolling art fascinates him, and were the inspiration for his book, Transatlantic Style/ Stile Transatlantico, exploring and studying the cross pollination of American and Italian auto design in the post war environment, in conjunction with an exhibition at the Blackhawk Museum. Read VT’s Review

Donald has followed so many different roads in his life and there have been many changes. He was once asked back in his marketing days, “Donald where do you see yourself in ten years?” with a laugh he replied, ”I have no idea!” Ten years before, he had been a classical opera singer and ten years from then he had become a classic car appraiser, judge, author and TV personality.

We will check back in ten years and see if he has it all figured out.

Watch this space.