A Good Problem to Have: Andy Greenberg’s Timeless Trio of British Greats

Cars made a lasting impression on Andy Greenberg at a very early age, literally. His mother remembers her son falling asleep on his collection of toy cars and waking up with their outlines imprinted on his face. Luckily, those impressions didn’t last long, but others have lasted a lifetime. Some of his first words were “top-down.” Both of his parents had cars, and one was a convertible, but no matter which car they put him in, he would pipe up, “Top-down, top-down!”

Greenberg’s biggest thrill was when the car would go wrong, and he and his father would have to figure out how to make it run again. Young Andy loved the adventure. His gateway drug was a pedal car with a vanity plate that said “ANDY.” Then it was a go-kart, a two-stroke that wasn’t all that great, but his dad found a more robust four-stroke model, and it was hammer down. 

Greenberg tore around the courtyard of his parent’s house on Long Island, and on the weekends, he was taken to an empty parking lot for a special treat so he could really wind it out. Occasionally, when no one was around, he hit the streets. He loved the feeling of speed and being in control. And when he wasn’t behind the wheel, he learned to take apart the kart’s engine and put it back together.

Greenberg was always drawn to English cars, a point reinforced when he went to camp at 10 years old, and all the counselors had MGAs and Austin-Healeys. Those cars stuck with him, but one of his first cars was the polar opposite: a 1958 Buick Special convertible. 

“It was Candy Apple red with a giant matching red steering wheel,” Greenberg remembers. “Everything was bright red with massive chrome bumpers. It drove like a boat, but I liked it. I especially loved the tube radio. You had to wait for it to warm up before you could listen to music.”

Then, in 1961, the Jaguar E-Type came on the scene, and like millions of people around the world, Greenberg thought it was the prettiest, sexiest, most wonderful thing he had ever seen.

“Back in the ’50s,” he says, “my father had a Plymouth convertible. It broke down on the way back from the city, and we somehow made it to a garage. The owner told him he couldn’t fix the car until tomorrow and lent my father his car, an XK Jaguar roadster in Winter White. He drove it home and was so excited. He cleaned out the garage and drooled over it. My mother had a different idea. She told him are you kidding? You have a family; this is not the car for us.” 

That was that, but Andy Greenberg never forgot his father’s enthusiasm. “In 1969, I was 17 and had just gotten my license, and I didn’t have the funds for such a machine. I reminded my father of his unfulfilled dream of owning a Jaguar, so we went shopping, and I got him to buy the E-Type. But it really wasn’t his thing. His back was stiff, and it was not an easy car for him to get into and out of. In the long run, he wasn’t very excited by it, but I was.” After some finagling, the E-Type became Andy’s car. 

“And now I have driven it around 235,000 miles. All of which have been gentle miles and in nice weather,” he adds with a big, sly grin. “I haven’t fully decided if I like it, but I’m beginning to think it has made a positive impression on me.”

What’s particularly amazing about Greenberg’s long-term ownership of the Jag were his enthusiastic early years, otherwise known as his teens and early twenties. How did an E-Type with a young enthusiast behind the wheel not get wrapped around a tree? Well, sometimes you just get lucky.

 “Late at night, on a windy road showing off for a beautiful girl, I over-cooked a turn, and I knew we were going off the road sideways, and there was a stone wall looming. I saw it coming, and I thought to myself, too bad you can’t redo the last nanosecond of your life. But I got lucky. There was soft mud, and it just grabbed the car, so we didn’t hit the wall. We dug the car out, got back on the road, and finished the trip safely. The girl with the beautiful eyes that were very wide when we went off the road disappeared after that, and I never saw her again. But the car survived, and that was more important to me. It was the real keeper.”

Greenberg sampled other cars like Triumphs and MGs (and his stepfather’s race-prepped Datsun 240Z), and those little Brits were fun but didn’t fulfill him like the E-Type did. At the same time, Jaguar wasn’t the only British marque of his youth that influenced him. 

“My parents moved to a new house when I was 10, and I had a friend across the street whose dad had a Series 1 DB4 Aston Martin. I was totally enthralled with that car. I used to love getting rides in it and I’d help wash it. When he came home at night, I could hear him coming up the road, and I would press my face up to the window just to watch the taillights disappear into the garage.”

Sadly, the DB4 ended up getting totaled. No matter: “My friend’s dad went out and got himself a DB6,” Greenberg says. “Again, I was enthralled.”

During his early 40s, Greenberg became good friends with Lance Evans, the founder of Pennsylvania Aston Martin specialists Steel Wings. Greenberg was on the hunt for his own DB6. “I had driven a DB4 and DB5,” he says, “and I just liked how the DB6 with the longer wheelbase went down the road.”

Evans soon found a DB6 for Greenberg, but it had been off the road for a while, and the original lacquer had become chalky. Though Evans assured him it was mechanically solid and the paint would buff out, Greenberg balked and passed on the car—a decision he immediately regretted. “A short while later, the person who bought it sold it to me—with a lovely shine and at a premium.” 

While reviewing the paperwork, he says, he discovered that the car’s original owners were Sonny and Cher. “I drove that car all over as well. It didn’t compete for my attention with the E-Type because it was a different experience. They both had their own personalities and gave me a different ride, and I loved doing what I could to make them more reliable, so I tended to carry a lot of spares and tools around to make repairs on the fly.”

On a rally with the Aston Martin Owners Club in 2009, however, things didn’t turn out how Andy would have liked . . .

“On a beautiful, bright, clear spring day on a straight stretch of road, I was following another Aston that made a left in front of me. There was oncoming traffic, so I stopped. A car driven by an elderly person who was out of it had cut into our group and slammed into me while I was waiting to turn, doing what the police estimated was 70 mph.” Greenberg was able to limp his Aston off the road but could smell gas and knew the tank was badly damaged, so he quickly shut it off and got out. An ambulance soon arrived, but not before Greenberg was able to call Lance Evans and his partner, Jon Clerk, who were on their way to Lime Rock. “They came and collected the car.”

Greenberg took stock of his roughed-up DB6. The steering wheel was bent up like a pretzel from his death grip on it. The car absorbed the shock, which went right through him to the front of the vehicle, where the engine was ripped from its mounts and the cam covers dimpled the bonnet.

With all that damage, the car could still be repaired, if the right people touched it.

“It took some time to deal with the insurance, and I was a bit ambivalent. I didn’t want to give up the car, but I wasn’t in a rush to get it back, either. Finally, I entrusted the car to Raymond and Dwayne Nosworthy [of Westchester Classic Cars & Coachwork Ltd.]. “Raymond made the frame better than new, and his son Dwayne was ready to give it a new coat of paint. I decided I wanted to change the color and have a fresh start with new karma, so I went in search of the right color, even so far as going to Newport Pagnell to go through their archives.”

Months into the process, however, Greenberg was sidelined with some health issues. “I was weak and had trouble moving around, so I thought this would be an excellent time to catch up on my car magazines and catalogs.” In the RM Sotheby’s catalog for its upcoming auction in Scottsdale, Arizona, a beautiful DB4 GT caught his eye. “I thought to myself, this might be just what the doctor ordered and get me back in the groove. I spoke to the previous owner, [race and sports car specialist Jack Boxstrom], to specialist Don Rose from RM, and to Jon Clerk, who had restored it for Jack. They gave me the green light.” 

RM extended Greenberg a line of credit, and he put in a bid. And though they told him they could set him up to bid online, his health issues stood in the way. “This is my number,” Greenberg told them. “If it hits, call me. If it doesn’t, call me in the morning, I’m going to sleep.” Don Rose called him that night with the good news. 

“He called again in the morning and said they had an offer for me. The underbidder didn’t want to let it go. He was ready to offer me $100,000 to let him buy the car for my winning bid. Easy money was not something I had experienced in my life, and it had its appeal, but I didn’t think twice. I said ‘thanks, but no thanks’. I was happy to have the car.” Greenberg had it shipped to Steel Wings, and they went through it. 

There was snow on the ground in Pennsylvania when Greenberg was able to go see the car, so he just sat in it. Just as it had been the first time he laid eyes on an E-type, “it was love at first sight. Not for a second was there any buyer’s remorse.”

By the time the good weather returned, so had Greenberg’s health, and he was ready to drive it. “The DB4 GT differs from the DB6 and the E-Type, but they all resonate with me differently.” Each car is unique and takes him on a different journey. They each connect to other parts of his life. “I have a penchant for these cars. I crave and enjoy them,” he says. “I like looking at them. I like thinking about driving them. Some things in my life did not live up to my fantasies or expectations, but these three cars have never let me down in that aspect.”

At present, he is completing a beautiful garage across from his home in Connecticut that will house the three Brits. “For one reason or another, I have never had all three cars in the same place at the same time.” Which brings up an interesting conundrum: If they’re all sitting there side by side, how will Andy Greenberg choose which car to take on a drive?

 “I will have to let you know in a follow-up discussion, but I think it’s a good problem to have. I have no doubt I will work out a satisfactory response.”