Travel back 100 years ago to Martha’s Vineyard. It’s the end of the Roaring Twenties, which will soon collapse into the Great Depression. The Island population is under 5,000, and by the early 1930s, one-third of the population is on some form of government relief under Roosevelt’s New Deal.
In this uncertain and relatively idle time, people pulled together for Sunday gatherings, and a new game called softball was just becoming popular. The lore is that the game was invented in 1887 on Thanksgiving Day, when a Princeton student rolled up a boxing glove and threw it at a Harvard student, who hit it with a broomstick. And softball, which was sometimes called “indoor baseball,” was born. It became a way to keep baseball skills sharp through the winter. It officially adopted the name “softball” in 1926, and grew in popularity during the 1930s.
During the early years of its history, the Chilmark softball game was established in the backyard of the Flanders family in Menemsha as a Sunday morning neighborhood pickup game. Following church services, families would gather, choose sides, and play until lunchtime. When the game outgrew the Flanders’ backyard, it wound up in Muriel Toomey’s expansive yard off the road to Gay Head, now Aquinnah.
Fast-forward half a century to the mid-1980s. Toomey’s field was sold, and the new owner planted multiple trees in what had been the ball field. The diamond moved to the softball field of the West Tisbury School, and then to behind the West Tisbury fire station. Here it remained for a decade.
During this time, photographer Peter Simon took on the unofficial role of softball manager. He and Jim Brooks, team captains, would choose sides. This was known as “The Era of the Chosen.”
It was in 1984 that this writer first started playing. By the seventh inning of my first game, I was hooked. Those games were serious and competitive — or so it seemed until the kibitzing began. There were arguments about everything. Sometimes the arguments almost took over the game. But Bill Edison, the longtime commissioner, would stop the game when the quarreling got out of hand and consistently remind everyone: “Time is running short — play the game! Summer is fleeting.”
Around 2002, the game moved back to Chilmark, to a field off Peaked Hill Road. This was accomplished through the efforts of longtime players David Flanders, Billy Meegan, and Peter Simon, and of course Edison, among others. Some of these legends have passed on, but their spirit remains, and the game remains, too — with opening day set, as always, for the Fourth of July.
Chilmark softball has a unique longevity as a pickup game — an informal gathering of players who come together and choose sides. It may well be the longest continuing pickup softball game in the country.
The custom now is for all the players to throw their gloves in a pile; the gloves are randomly separated, and that is how the teams are decided. “Gloves in!” is the way each game starts.
Once the game was moved back to Chilmark, it took on a gentler and much-improved culture. Long-standing player Jason Balaban remarks: “Although we were all trying our best, there was always something larger than wins and losses. Comradery, friendships, history, dreams were all being formed or played out in this universal summer game. It was and still is an instrument transmitting and transferring us to our childhoods. There’s a reverence for the simple act of playing ball on a field with friends.”
On July 5, 2009, the field was dedicated as Flanders Field to the memory of legendary Chilmark player David Flanders, who had died the year before. The dedication ceremony began with a bagpiper in full Celtic regalia playing “Take Me Out to the Ball Game,” followed by informal comments by several long-term players. These included commissioner Edison, Hans Solmssen, Peter Simon, and Peter Neuman.
Solmssen, our oldest player at 89, reflects on Flanders as one of the true founding fathers of the game: “What I vividly remember is David Flanders stepping up to bat. All the infielders would drop their gloves, because we knew David would drive the ball into the pine trees for a home run.
“A Chilmark fire engine was visible in deep right field. The new scoreboard sign was christened with a bottle of champagne. Fran Flanders, David’s daughter, tossed out the ceremonial first pitch.
“It’s not Fenway Park. But in the early years at Peaked Hill, there was a big ugly boulder in left center field with poison ivy growing around it. It was referred to as the Green Monster. The field had its ups and downs and dips that could be lethal while tracking down a long high fly to center field. If a fly ball hits the dirt road beyond right field, it’s referred to as a Kerouac. Why? Because it’s On the Road!
“Our present-day first baseman, Ed Eger, has set records with his majestic Kerouacs. He refers to that ‘lumpy, pockmarked field of dreams’ where the focus is ‘to have fun, have some laughs, play some softball, not take ourselves too seriously, always be a good sport, and make lifelong friendships.’ Those are also guideposts for life. It’s important to be reminded of these things every summer, to help me get through the winter.”
Although there is no official dugout, there is a large players’ bench: the Tony Horwitz Honorary Bench, a tribute to the late Pulitzer prizewinning author who was one of our most enthusiastic players, as well as the in-game scribe.
Chilmark softball may not have had Babe Ruth visit, but still, it has a storied history.
One of the more searing memories is of Hall-of-Famer Jackie Robinson, who attended one game back in the early ’60s as the guest of Peter Simon and his mother, Andrea. In the ninth inning, with men on base, Bob Crichton stepped back from the plate and announced, “Now batting for Crichton, Jack R. Robinson.” He handed the nearly blind Robinson his bat and stepped away. Robinson fondled the bat and peered out toward the pitcher. He clearly wanted to give it a try, but then he handed the bat back. What followed was the silence of respect that no one else was ever accorded on the field.
“There were Bunyanesque figures out there,” wrote Jim Kaplan in the Vineyard Gazette in May of 2006. “Chilmarkers such as David Flanders who hit tape-measure homers, Ozzie Fischer, who came off the UMass varsity to hit line drives, machine-like, over the shortstop’s head, and Dan Cabot of West Tisbury, who caught errant throws that seemed to sail halfway down the line. There was Peter Simon of Chilmark, always barefoot, pitching or making underhand throws from the outfield.”
Jerry Kohlberg, “a bald little guy with a red elf’s hat,” participated in perhaps the most unusual double play in Chilmark history when a ball bounced off his head toward Peter Neuman, who caught it.
Those longtime umpires were memorable, too, Kaplan continued: “Roger Baldwin, who founded the American Civil Liberties Union, ruled ‘with the thundering authority of an Old Testament prophet.’ Rabbi David Weiss of Philadelphia had a strike zone that extended unto the heavens.”
The game became fast and competitive. Filmmaker and summer resident Spike Lee appeared in uniform, and was part of the first and only triple play in the almost hundred-year history of the game. Here’s how this writer remembers it: There are runners on first and second, no outs. Lee, at first base, snares a line drive and tags first base before the runner gets back for the second out, then whips the ball to the third baseman to snag the runner who’s taken off at the crack of the bat. The celebration is astounding on all sides. High-fives, low-fives, hugs all around.
The late Bill Edison believed the game needed to revert to being a true pickup game. He introduced the notion, still used, of 20 to 30 players throwing their gloves in a heap, and letting the youngest player randomly fling the gloves into two piles. Thus, two teams were randomly created each time. If the randomness resulted in top-heavy lineups, there would be some negotiation so that the lineups were more evenly divided.
Edison’s most profound contribution to the reestablishment of the game in Chilmark was the promotion of friendships, good sportsmanship, and high-spirited fun.
Conversations with his daughter Miranda reveal his long-standing friendship with Lawrence Ferlinghetti and his affinity for the San Francisco Beat era of the ’50s and ’60s. Edison served as Ferlinghetti’s part-time bartender at El Matador; this was the bar next to City Lights, the celebrated bookstore frequented by all the great writers and jazz artists of the time. He got to know Jack Kerouac and William Saroyan, as well as Allen Ginsburg. In the early to mid-’50s, Edison and his wife Lydia started spending their summers at their magical cottage in Menemsha. The late Peter Simon reflected on those years, writing, “[Bill] was the informal coach for all the younger players, and he taught me the nuances of the sport … I’ll always be grateful to him for taking me seriously and showing me how to play to my strengths. He used sports as a life lesson and got kids to believe in themselves.”
Three commissioners meet near the end of the season to determine awards such as the vaunted Howie Hustle Award, named after Howie Bromberg, long-standing catcher. He would wear a mask and kneepads and run to first base on every ground ball to back up an errant throw. Howie, of course, was the first recipient of this award, and to this day he hands out the award to the season’s player who represents good sportsmanship — and of course, hustle.
Paul Iantosca recalled taking his son-in-law to the game, assuming he himself would just watch it. But “everyone was warm and welcoming. I watched players from 14 to 84 just out on the field having an inordinate amount of fun and laughter. Everyone was enjoying the game as if they were kids again. I was hooked, and threw my glove into the pile for the second game. What I realized as the morning progressed was that I was amidst a group of the kindest and warmest people I had ever experienced. I won an award that year, the Howie Hustle Award for the most infield hits.”
As the weekly turnout of players increases dramatically, especially during August, the commissioners try to implement rules involving safety: limiting the number of outfielders, calling balls and strikes, establishing ground rule doubles, etc. But after only two games of the “season of the rules,” the rules — particularly on called balls and strikes — begin to slowly be disregarded. The one rule that persists, however, is the rule of coaching a youngster who may be on base and making sure that younger player does not get hit by foul balls or errant throws.
Peter Simon died unexpectedly in November 2018. He hadn’t been able to play much in his later years, but he’d had almost 50 years of Chilmark softball. In his great collection of photos “To Everything There Is a Season,” he included an entire section to the softball game. He would recall: “Playing softball on the Vineyard has allowed me to be the kid I never was able to be.”
At the end of the day, what makes this game so special is the spirit that has developed but that remains similar in its formula to those early days almost a hundred years ago. It’s about families — moms and sons and dads and daughters. It’s a social event where friendships have formed and exuberance and joy accompany a well-played game. It’s the game of summer.
Players have come and gone. The famous, the not-so-famous, the year-round Islanders and the summer folks. Hedge fund founders and hedge trimmers, fishermen, artists, writers, carpenters, architects, teachers, doctors, lawyers, psychiatrists, surgeons, pilots, writers, poets, photographers. Moms and sons and dads and daughters. All playing a game that has no clock. It’s the timeless game and we’re all just kids again.
Heading out to Peaked Hill on Sunday mornings this summer, we will recite the resonant words of Bill Edison: “Time is running short — play the game! Summer is fleeting.”
Retired psychotherapist Sig Van Raan has been playing Chilmark softball since 1984. He has three grown children and a growing brood of grandchildren who are regular visitors to his home in West Tisbury, where he lives with his wife, Susan Dickler.