Robert Wing Gray
June 24, 1940 – May 30, 2021
EULOGY by Benjamin Zucker
My great friend, Bob Gray, passed away last month. His story has been so wrapped up with Yale 1962 and, in a certain way, with the Yale Daily News. A story of friendship and a story of family and love. I met Bob through the “heeling” process at the Yale Daily News — when one tries out for the school newspaper. I was told that heeling was very, very difficult and required perhaps 20 or 30 hours per week. Hours that I couldn’t really spare from schoolwork but, ever the gambler, I signed up. The heeling process quickly divided itself into trying out for the “business” side or the “editorial” side. It was a highly competitive situation. One got points for each of the stories one wrote or for the ads that one sold. My father was in the jewel business and the feather business. I wanted to be the great American novelist but somehow family prevailed and I joined the competition on the business side.
Bob’s father was a banker for the Rochester Savings Bank. On the weekends, Bob and his two brothers and his sister would work on the family farm in Penfield. From the first moment, Bob and I were pals and not trying to compete with each other. Pretty much everybody else that I saw, with the exception of Paul Torop and George Ackerlof, seemed to be highly competitive. Lance Liebman didn’t seem competitive — he was just simply brilliant and could type faster than anyone in complete paragraphs, no rewrites, and knew his way around The Yale Daily News because of his cousin, Bud Trillin. About two weeks after we met, I was going home and invited Bob to join me. My parents were immediately head over heels for Bob and, as Bob had never sampled French food before, over the years Bob was a permanent visitor to our New York apartment.
Bob’s father was the Vice President of the Rochester Savings Bank. He never became president but he was an early investor in Xerox Corporation. While many people in Rochester invested in Xerox, over the years, as their profits grew, they tended to bail out. Bob’s father never did. That was, in my opinion, a model for Bob’s thinking about business. He wanted to be part of inventing some product, just like Kodak, the other great Rochester company. Bob revealed to me early on that he had some ideas about inventing a perpetual motion machine. I kept this secret and only told Paul Torop.
As the competition for the Yale Daily News grew in intensity, I believe we knew how many points had been garnered and how close we were to winning. I think the top 20 of us got a place on the newspaper. Bob and I finished high on the business side. And for the remaining three years, we worked on the newspaper together. In our second year, we had the idea together, I believe it was my idea (one tends to take credit for all good ideas) and Bob wasn’t sure, to have a newspaper that would be handed out free to many students at different colleges throughout the United States as a career opportunities guide. It would be called the Yale Guide to Career Opportunities. Where would the magazine make a profit? Well, we would sell advertising. And Bob figured out that we would have a standard 5/8 of a page ad—no more and no less—which would make sure the advertisers would not chisel on the ad purchase.
We started the summer after our second year at Yale. The first issue was a Career Opportunities Guide in Real Estate. For that, we interviewed people in the real estate world. They balked at the $600 cost of an ad. So we quickly dropped the price and offered ads at $200. In the summer, we got enough ads to ensure that the paper could come out. But the target required so much paper that as Bob said, “We are going to need a warehouse full of paper, which we will have to pay for in the summer even though we won’t need the paper until the fall. This was a moment of truth. I said to Bob, “What happens if we can’t pay for all the paper and the ads don’t continue rolling in?” Bob laughed with that terrific Scot-American laugh of his and I understood that we were on a path. No going back.
So we sold the edition. We delivered the papers at the beginning of our third year at Yale. And we were quite successful. Meanwhile, I would visit Bob in his room with his roommate, Bob Green. I found it linguistically very charming that Yale would place Robert Green and Robert Gray in the same room together as freshman. They continued on as roommates until senior year in Calhoun. By that time, I would say we were attending the Yale Daily News (the oldest college daily) more than we were actually going to our classes. But it was very heady stuff, writing articles, selling ads, surveying the politics of Yale and the camaraderie of the people on the News was extraordinary. The biggest success we had was Career Opportunities in the Insurance Business. Paul Torop became the editor-in-chief for that edition and was handsomely reimbursed. To this day, he still laughs at the “easy money, far beyond his expectations.” At the end of the third year at Yale, we had proposed a contract to continue with the publication of Career Opportunities with some of the money going to the Yale Daily News to buy equipment and the balance to ourselves as the staff. After Junior year, Bob stayed in my parents apartment the entire summer and we agreed to split the profits in the percentage that Bob presented.
I wanted to go to Paris with Dick Zorn. Bob wanted to spend the summer talking with my father, using the Pearl office as a selling base and eating my mom’s cooking to his heart’s content. We were a colossal financial success. I earned $40,000 for my share of the profits. I like to think of it as 14 times our college tuition for that year. Now Bob and I started to think of ourselves as venture capitalists. We decided that we would buy a real estate building on Riverside Drive and 84th Street. Also, Bob wanted to enter into the electric car business. After college, I graduated from Harvard Law School and Bob went to the University of Chicago.
I stayed in touch with Bob through all the vacations. He would come to New York occasionally and we made plans to really get together in New York after law school. In May 1965, I was walking down Massachusetts Avenue in Cambridge with Paul Torop when I spotted two beautiful women carrying four bags of heavy groceries. Bright as a button, I raced over to one of them and said, “Oh my god, what is America coming to? You two women having to drag these groceries to your apartment.” The woman said with a smile, “Oh. Of course, you can help us.” And we walked a block and went up to the second floor of a white clapboard house. I don’t know why I said this, but I looked at her and said “I have a friend who is coming to New York who you really would love to go out with. He’s perfect for you.” And she said, “Fine. As a matter of fact, in a month I’m going to be in New York.” I quickly called up Bob in Chicago and said, “Bob, I’ve found the girl you’re going to marry.” And he couldn’t stop laughing and within a year, they indeed did get married.
Bebe and Bob had an extraordinary marriage. Three children, Katherine, Al and Josh. Bob worked for Winthrop, Stimson, a longtime Yale law firm in New York — the firm of Henry Stimson, with a list of extraordinary clients. Bob and Bebe reminded me a bit of Nick and Nora Charles in the Thin Man stories by Dashiell Hammett. She was incredibly smart and he knew it. In a sense, they adopted my parents as their own parents and they lived a few blocks south on 86th Street and West End Avenue. Bob got a chance to move to open up a London office for Winthrop, Stimson and lived there for approximately five years. These were very happy years for both of them. They lived just off Hyde Park. When they returned to New York and he continued to work for Winthrop, Stimson, theirs was a life filled with working on the Armory show to raise money for charity. Bob was extremely busy as an advisor to the Singer Sewing machine company and other blue ribbon clients. Bob was equally a marvelous business man as well as an incredible lawyer. He looked like the farmer he was. Bob Green used to say, “Close your mouth Bob, you’re going to catch flies.” And he had an abstracted look but his mind was working at all times. He was a very, very good trial lawyer.
When Bebe was 45 years old, she was diagnosed with lung cancer even though she had never smoked. It was an immeasurable tragedy that had also befallen her mother at the very same age. The sickness was quick and brutal. Bob spent many years raising his children himself. He had the good fortune to marry a second time to Nancy, who had children of her own. Her son Donald passed away, but Andrew remains ever close to the Gray family. They all put a lot of effort into having a strong, blended family, never an easy task. Nancy died after nine years of marriage.
Bob was my lawyer but he was much more than that. He always encouraged of all of my dreams and hopes and plans. He had been Al Chambers’ lawyer, also on the News with us. He would provide advice for anybody and it was always very sound. At the same time, he never abandoned the idea of going into business where, in a certain sense, his first love was. Of course, he and I should have concentrated on the electric car business. We should have bought that building on 84th street. Woulda coulda shoulda.
Meanwhile, Bob was always struck by the friends he had at Yale, and the adventures that we had. We would never tire of talking about them. After Bob retired, Winthrop, Stimson was acquired by Pillsbury, one of the largest firms in the United States. He still had an office that he would go to, but mostly it was a moveable feast for us: each of us explaining how our next brilliant scheme — whether it was buying a wonderful gem or a sub company he was interested in or developing a lithium mine. To the very end, Bob never lost the exuberance and the sometimes quixotic plans to be a creator of a totally new business.
At the age of 75, I noticed that our kids had suddenly become smarter than we were, and they knew it. Bob was so proud of Katherine’s achievements in government and business. Bob loved talking about Al’s technical prowess. We all enjoyed, Bob, Al and I, going out to movies together. Bob adored Josh’s exuberant love of life and travel. Bob’s trips with Josh were like Huck Finn and Tom Sawyer, roaming around the United States, forever teenagers. I pointed out to Bob they should be the bosses and we should listen to them. Mostly, Bob did allow that, even though one time (because he was expressing illogical political beliefs), Al, who’s very adept technologically, fixed his television set so that he wasn’t able to receive Fox News. I told Bob, “You better be really careful because Katherine, Al and Josh may get even more strict with you unless you do what they tell you to do — such as not eat chocolate ice cream.” Bob was very self aware medically. He got one of the finest stent experts in the United States to install a stent in him. After five years, he needed another stent.
His kids, as the years went on, became closer and closer. In the last year of Bob’s life, they really became a unit to help him and take care of him. To the very end, Bob was completely lucid and laughed at my jokes. He died as he lived, part of a circle of friends, calling Chris Cory, Bob Green, Richard Davis, Paul Torop, myself, and his brother Bill on the speed dial that Al had set up for him. He will never die.