This is the point in the season when the game goes into a full-blown time warp. After two weeks in their all-whites at Wimbledon, the birthplace of tennis, many ATP pros hop straight across the Atlantic to visit America’s version of the All England Club, the Newport Casino. The building, an early design of the Gilded Age's house architectural firm, McKim, Mead, & White, is where the U.S. Nationals (now known as the U.S. Open) were first held, in 1881. The tournament, and big-time tennis, left the old-line resort city and its rows of mansions long ago—the Nationals moved to Forest Hills in 1914—but for one brief, strange, and electrifying moment in July of 1965, the staid old town and its staid old sport found themselves perfectly aligned with history, and the rapid changes in it that the 1960s were producing.

Fifty years ago last week, the Casino held its annual mid-summer men’s tournament. But this was like none that it had hosted before. To start, for the first time in the Casino’s 85-year history, professionals were allowed to walk on its lawns. Ten male pros, including Rod Laver, Pancho Gonzalez, Ken Rosewall, and Pancho Segura, were invited there by tournament director Jimmy Van Alen, a child of Newport's mansion row and as unlikely a revolutionary as history has known.

“A lot of people,” said one of Van Alen's professional ‘guinea pigs,’" Butch Buchholz, “thought the grass would turn brown when we pros stepped on it."

Five decades later, the tournament they put on still stands as the most unconventional in the sport’s history.

Van Alen is most famous now as the inventor of the tiebreaker, even though he hated the 12-point version that became the standard. He wanted “sudden death,” in the form of a nine-point breaker, rather than what he derisively termed the “lingering death” of the 12-pointer. By 1965, Van Alen, a ukele-playing former captain of the Cambridge (England) tennis team who had grown up with Rembrandts on the walls of his bedroom—Bud Collins dubbed him the “Newport Bolshevik”—had been on a decade-long war against deuces of all sorts.

It had all started when, as tournament director in 1954, he had watched in an ever-escalating rage as two lesser-known American players, Hamilton Richardson and Straight Clark, played a final that ended with the tongue-twisting score of 6-3, 9-7, 12-14, 6-8, 10-8. The match lasted long enough that Van Alen had to move the doubles final, which included Rosewall and Lew Hoad, and which most of the fans had come to see, to a smaller side court without enough seats. From then on, Van Alen was hellbent on ridding the sport of those “damnable deuce games.”

“Any fathead can do better than this,” he said of tennis’ scoring system.

But the tiebreaker was only the first of Van Alen’s many hare-brained schemes for revolutionizing the game. None of them were ever seriously considered by his fellow amateur tennis officials—they thought Van Alen was a traitor to his sport, if not his class. So he took his money and his schemes to the dark side, to the pros. Van Alen’s experimental tournament at the Casino in ’65 finally gave him a chance to do tennis in his own loony, exciting way.

The Newport Bolshevik offered $10,000 in total prize money, a stratospheric sum in those days, but the cash came with a catch. The old pros had to play by his new rules, known as VASSS—Van Alen Simplified Scoring System. That included the tiebreaker, which had yet to be named and was referred to at that point as an “extra game” (for some reason, Van Alen's original tiebreaker was an even-numbered eight-pointer; naturally, the first one played ended at 4-4, which necessitated a second tiebreaker).

VASSS also jettisoned the traditional knock-out tournament in favor of round-robin groups. Games and sets were the next to go; matches were scored point-by-point, ping-pong style, up to 31. The money that each player earned—Van Alen awarded $5 per point won—was tallied up and flashed on an electric scoreboard above the court. When a match was over, Van Alen stood beside the court and rang a bell.

“Sounds half-VASSS to me,” Segura quipped.

And what about the court itself? It wasn’t safe from Van Alen, either. He had a new service line installed three feet behind the baseline, to deter the serve-and-volleyers who then dominated the game to an often-boring degree (if he were alive now, perhaps the “Van Alen line” would be drawn three feet inside the baseline). The players generally went along with the experiment, though Pancho Gonzalez threatened to quit mid-match. “How did I get myself talked into this?” he yelled. The worst of it for the pros may have come at night, after the tennis was over, when Van Alen held parties in the Casino and performed for them on his ukelele.

In the end, the one thing that didn’t change were the winners. Laver finished first, Rosewall second. And while only the “extra game”—the tiebreaker—survived from his scoring system, Van Alen did introduce another element to pro tennis that would make a strong comeback in the following decade: electric lighting for night matches.

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That's where the second part of our Newport summer of ’65 saga picks up—with electricity. Two weeks after Van Alen took down his lights and his scoreboard at the Casino, another revolutionary figure arrived in town, similarly bent on shocking the traditionalists in his own line of work. On July 25, Bob Dylan went electric at the Newport Folk Festival.

The 24-year-old Dylan, along with his partner in pure-minded leftist politics, Joan Baez, had been the darlings of that gathering the previous two years, and he was the headline act again in ’65. This time, he chose the festival to make his break with the folk purity that he had begun to find suffocating. Rather than the socialist-style work shirts and jeans he’d always worn, Dylan showed up in a leather jacket. Rather than strumming his acoustic guitar (symbol of all that was authentic), he plugged in an electric guitar (symbol of all that was commercialized) for the first time anywhere.

Rather than sing with Baez, Dylan was backed by the all-electric Paul Butterfield Blues Band. They played and the crowd booed until, as legend has it, old folkie and longtime Dylan supporter Pete Seeger pulled the plug on the whole thing (a story that is likely more legend than fact).

Dylan, of course, had the last word. After his electric debacle, he wrapped up his later acoustic set with a not-so-subtle message to his folk cult: “It’s All Over Now, Baby Blue.” Rock music, for the first time, was going to be taken seriously, and Dylan was officially a star.

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Is it nothing more than a coincidence that Van Alen’s kooky tennis tournament and Dylan’s electric debut happened within two weeks of each other, in the same small resort town? While the events represented two separate worlds, there were crosscurrents that traveled between them. Each was part of the same set of changes that transformed the U.S. over the course of that decade. In both cases, a refuge from commercialism—amateur tennis and folk music—had been successfully invaded.

The Newport Casino was the second old-guard tennis establishment to welcome the pros; Longwood in Boston had done the same the year before when it held the U.S. Pro Championships for the first time. It’s clear now that these were the necessary warm-up events before the pros could leap the highest club walls of all, those at the All England Club, which they did when they were invited to play an eight-man tournament there in the fall of ’67.

Tennis was running alongside the rest of the U.S. in the 60s, a decade that was about the collapsing of hierarchies and dissolving of boundaries. The inspiration had been the end of segregation in the South, but the idea radiated everywhere. By ’65, the liberalism that began the decade was beginning to morph into the more confrontational radicalism that would end it. That year the U.S. rapidly escalated its commitment in Vietnam. In the spring, Martin Luther King led the carefully organized voting-rights marches in Selma, Alabama; in August, deadly race riots broke out in the Watts section of Los Angeles.

At Newport, Dylan, famous for his protest sing-alongs, took a more confrontational stance with his audience. That year and the next, he erased the boundaries between rock and folk, between the commercial and the non-commercial. The same went for his accidental partner in historical crime, Van Alen. By desecrating the previously pure Casino lawns for three years—he would hold his VASSS event in 1966 and ’67 as well—he made it easier for tennis to collapse another hierarchy: the age-old distinction between gentlemen (amateurs) and tradesmen (professionals). Van Alen let the pros inside the club, and they never left. For music and tennis, breaking down these barriers led to stunning success. Dylan was at the center of a pop music explosion in '65 and '66, while professional tennis—with an assist from the tiebreaker—would prosper beyond Van Alen's wildest and weirdest dreams. Of all the revolutions of the 60s in the U.S., it was capitalism's that had the biggest impact.

It’s doubtful that Jimmy Van Alen played “It’s All Over Now, Baby Blue” on his ukelele on the final night at the Casino in that revolutionary summer of '65. But it would have been appropriate.

This post has been updated from a version that ran in 2011.