For many Yalies, The Game is an annual opportunity to release anti-Crimson vitriol, brag about superior parties and generally berate Yale’s longtime rival in Cambridge.
But Richard Sperry ’68 and Roger Cheever, Harvard class of 1967, have overcome this famed rivalry: This year marks their 37th consecutive joint attendance of The Game.
Although both attended The Game independently while they were undergraduates, they did not meet until after graduation, when they were both stationed in Newport, R.I., at a Navy training center and were randomly assigned to the same room.
When Cheever entered the room for the first time, he could tell Sperry was a sworn rival — Yale paraphernalia adorned the room. But the two nonetheless became fast friends.
When they found themselves on different ships on their way to Vietnam, it seemed like their burgeoning friendship might end.
“Sending mail from one ship to another in the Pacific causes a lot of problems,” Sperry said.
Still, the two kept in touch through postcards. And at one point, Cheever took a helicopter to visit Sperry in the Gulf of Tonkin; the two visited each other by helicopter several other times in Vietnam.
Serendipity intervened once again after Cheever and Sperry were released from service. The two found themselves living in Boston — Cheever is a native, and Sperry was attending Boston University School of Management — and they decided to rent an apartment together.
When the 1972 Game rolled around, “we just decided to go,” Sperry said. To heighten the drama, the two agreed that the alum from the losing college would pay for the tickets. The next year, with Cheever anxious to get his money back after the Bulldogs’ win the previous year, the two decided to attend again.
To this day, the bet still stands. About 10 years in, the two agreed they should keep the tradition going, and Cheever is “cautiously optimistic” about his chances this year.
Indeed, tradition is not something this pair takes lightly. In 2001, Cheever was faced with what is perhaps a Cantab father’s ultimate dilemma: attend The Game or watch his son, Witt, the captain of the football team at Middlesex School, a private boarding school in Concord, Mass., compete for the New England Championship.
Cheever chose to see his son play, but he was not willing to sacrifice the tailgating tradition entirely, rounding up several Middlesex parents to start his own tailgate at the championship game in Concord.
“It was a little more lively crowd than at most high school games,” Witt Cheever said in a phone interview from San Francisco. “He carried the tailgate over, if you will.”
Still, even with an impromptu tailgate at the Middlesex game, Cheever and Sperry did not want to break their tradition. That morning before The Game, the two had asked the head of Yale security to open the Yale Bowl for them at 8 a.m.
“We threw a football around, made toasts to each other, and then I drove straight to the train station,” Cheever said.
Though Cheever did not see The Game live, Sperry kept him updated via cell phone.
The two are glad Cheever did not miss that game entirely — because, at least by Sperry’s estimation, the pair has the longest streak of consecutive Game attendances in history. Out of curiosity, Sperry once put advertisements in the News and The Harvard Crimson seeking alumni challengers. One Cantab responded, but his wife, upon further inquiry, told Sperry her husband had missed The Game one year. Nobody else stepped forward. Although the investigation perhaps lacked academic rigor, Sperry said he is nonetheless confident of the record.
Beyond their long-standing attendance streak, the “H/Y Cheever/Sperry” tailgate, as the two have dubbed it, has become a tradition in its own right.
While the tailgate started in 1972 as a typical hot dogs-and-beer affair with just Cheever and Sperry, the tailgate has since evolved into a full-fledged event with about 60 to 80 attendees each year.
Like any good tradition, the H /Y Cheever/Sperry tailgate has historians: The two have been keeping minutes — they call it “the log,” from their naval days — for about 30 years, documenting every event of the tailgate.
Cheever and Sperry have other traditions when they reunite for The Game. The two use navy jargon at the tailgate, and each year, Cheever, Sperry and Jon Steffensen ’68 bring their signature foods and drinks. Steffensen brings deviled eggs and Bloody Marys, Sperry is responsible for tomato soup (made with sherry instead of water) and his famous steak sandwiches with an herbes de Provence sauce introduced to him by a French Air Force officer in Paris, and Cheever brings the Commencement Punch — a rum-based punch whose recipe has been passed down through Cheever’s family since Prohibition. The night before The Game every year, he and his wife have a “ritual tasting” to make sure the punch is just right.
As it has grown in scale, the tailgate has attracted its fair share of celebrity attendees. University President Richard Levin, former U.S. Ambassador to China Clark T. Randt Jr. ’68 and former Yale quarterback Brian Dowling ’68 have all made appearances. One year, Cheever and Sperry were confused at the Secret Service detail milling about in the crowd until they realized Barbara Bush ’04 was there.
But for everyone involved in the annual Cheever-Speery reunion, the primary impetus for making the trek to The Game each year is the sense of camaraderie between old friends and family.
“It’s a real family affair,” Steffensen said.
Indeed, Cheever brought Witt to the tailgate when he was only a few weeks old, and between Cheever and Sperry the two have amassed a following of Yalies and Cantabs who come every year. Sperry now works as a marketing executive, and Cheever is the associate vice president of principal gifts for Harvard.
“It’s a great excuse to get everyone together,” Cheever said.
Sperry added that many people stay at the tailgate and do not make it into the stadium.
Now featuring recent innovations, such as a gas grill and a flag to identify their tailgate, the H/Y Cheever/Sperry tailgate will convene this weekend as it has for nearly four decades, this time in Lot B. Cheever promises a good time.
“It’s a riot,” he said.