Richard “Ripper” Roy, an umpire for the Martha’s Vineyard Men’s Softball League for the past forty-three years, believes in delivering an impartial, civil ball game, without fear or favor. But there is one bribe he has been known to accept.
“You could give him hot dogs if you want good calls,” said Ben Madeiras, a pitcher in the league.
Roy’s love of hot dogs, fresh from the grills near the field, is so fervent that a group of players gave Roy a photograph of him eating a hot dog in his umpire uniform as a wedding present. How did he feel in that moment when the photo was taken?
“Hot diggity dog,” he replied with a grin.
Now, after more than four decades and too many Ball Park Franks to count, the stalwart adjudicator has decided to retire from his post. As the new season got swinging this year, he and Madeiras, who has played in the league for almost twenty years himself, reflected on what makes for a good umpire and what keeps people coming back to the softball diamond summer after summer.
The Men’s Softball League has been around since at least the 1970s, though some accounts put the start date decades earlier. The games currently take place in Veterans Memorial Park, the field behind Cumberland Farms in Vineyard Haven, on Mondays, Wednesdays, and Thursdays from June through August. There are currently five teams, and two games are played each night. They begin while the sun is shining, stretch through sunset, and continue after the lights come on. Sometimes a timeout is called when a skunk runs across the field.
Other wildlife makes appearances too. Madeiras has been coming to games since he was a little kid to watch his father play. Beyond the outfield is an osprey nest. “I remember the mother or father going out, getting a fish, coming back, dropping it off – just doing that all night until dark,” he said.
Madeiras’s father died when he was eleven. Since then, Madeiras has carried on the torch and found his home on the pitcher’s mound. Like a father and a son, an umpire and a pitcher have a special connection – one that can get contentious if the pitcher disagrees with the umpire’s calls. But that doesn’t happen between Madeiras and Roy. At least not often.
“Just like any other relationship, you have to respect each other. And, if you don’t agree with something, that’s fine, you know?” Madeiras said. “We’re going to go through life and have disagreements all the time.” (How often does he think Roy makes the right call? “Let’s say ninety percent,” Madeiras laughed.)
Not every player has this magnanimous spirit. Some have been known to talk back to Roy, telling him he got it wrong. Roy takes it in stride. An umpire must have the confidence to keep going anyway, to make call after call, knowing he’ll face objections. “I’m the easygoing umpire,” he said.
But that wasn’t always his position on the field. “You know how I got the name Ripper?” Roy asked. He cast his mind back to a moment several decades ago. “I’m a left-handed batter, and so when the first baseman was standing there, waiting for me to hit, I sizzled that ball so hard right by him. He turns his head and he’s like, ‘Jesus Christ.’ Yeah, I used to rip that ball.”
Now, the sizzle has cooled slightly and Roy is known for a measured respect for the game. Fair calls make an umpire good, but Roy has thoughts about what makes an umpire great. It’s about keeping your eye on the big picture.
Civility is also a necessary ingredient. “The only way I’ll throw you out is if you swear at me. I don’t tolerate the swearing when the fans are there with little kids,” Roy said – and kids come out in abundance, often to watch their fathers, uncles, or cousins play.
Although all kinds of people play in the league, some teams form based on shared experience. “There’s a team called the Scrubs, and they work at the hospital,” Madeiras said. His own team, the Highlanders, is mostly comprised of folks who work in the trades, as does he. When he’s not on the softball field, Madeiras works in landscape construction. And when he’s not building stone steps and pools, he’s coaching basketball at his alma mater, the Oak Bluffs Elementary School. Some of the kids he’s coached have left the court and joined him on the field. Madeiras wants to be a good role model for the next generation – like Roy has been for decades.
Roy’s decision to retire from his position wasn’t easy for him, he said. “They’re going to miss me, but I’ve been here for forty-three years. It’s just time for me to step down now.”
As the new softball season heats up, players and fans will have to put their trust in new umpires, but they won’t have to look too far to find Roy. He’ll be sitting in the stands now and then, watching the games, hot dog in hand. Will he be able to refrain from making calls from the sidelines? Yes, he said. He’ll just be there for the love of the game.


