Old Timers softball game benefits the Little League

They’ve been playing the Shelter Island Old Timers softball game for so many years that no one is exactly sure when it started. This year it was played on Oct. 10, a sparkling fall Saturday, with bags of ice for aging joints and snacks for all. The game, like every Old Timers game since the 1970s, was a way for players over 35 years old to raise money for the Shelter Island Little League.

In the tense minutes before the pitchers arrived, Tim Sheehan did not yet know which team he’d be on. “I think I’m gonna play 1st base today,” he said. 

“Yeah, limited movement,” offered another mature player.

Tim’s son, a 7th-grader, is a former Little Leaguer who now plays shortstop on the middle school team. 

Nearby, with the padding leaking from his aged cleats and one whole side blown, Marc Lava defended his look. “They’re vintage, circa 2004, he said. “They came out last year at this time. One time a year for this game.” Marc has played in the Old Timers game for three years in support of Little League and his son Noah, who is a player.

There’s a lot of lore around pitching at the Old Timers’ game, including the stealthy substitution of a grapefruit for the softball, just when someone yells, “Give him the heater.” This year’s game was grapefruit-free.

Brothers Mike and George Goodleaf returned as pitchers. They are notorious for throwing high-arching softball pitches with a spin, that are difficult to hit and drop right on the plate as strikes.  

The teams were Grey and Blue for the color of their T-shirts, which were available for purchase at the well-stocked merch table adjacent to the field.

Chuck Kraus hit one into the outfield for the Greys and took off for first as his wife Linda yelled, “No running for you! I don’t have travel insurance!” (They are about to go on vacation.) 

Later in the inning, Kevin Springer hit a base-clearing bomb, caught up with Chuck on the base path between third and home, and gave Chuck a pat on the rump to move him along.

A clutch play at third brought cheers from the sideline, “Whoo hoo! Whoo! That’s it, Robbie. Yeah, bro! Robbie Brewer.” Mr. Brewer was wearing a knee brace, and a teammate yelled, “Watch it, you’ve got to go to work on Monday!” 

The Little League umpires of the day were Jackson Surerus (home plate, grade 8), Oscar Sheehan (first base, Grade 7), Sloane Katta and Brookelyn Gulluscio (3rd base, Grade 7) In the outfield for the Greys, Mike Mitchell was coached by his son, who employed body English in an effort to move his dad into correct position.

In the end, George Goodleaf’s pitching on the Grey team kept the Blue’s offense in check. The final score of the seven-inning matchup was 20-12, but the two teams managed to come through the day with no disabling injuries and a little muttering about a pulled hamstring. 

The party after the game was donated and catered by Frankie at shelter Island Slice, an always generous sponsor of the Shelter Island Little League. Organizer and player Amanda Katta said the winner of the 50/50 raffle picked up the bar tab for players celebrating a great day with no injuries, and the Little League raised money to cover basic operating expenses and make costs more reasonable for the upcoming season.  

Ms. Katta said, “We always welcome additional donations from sponsors or community members to support pitching clinics, pay for umpires and equipment purchases.”

The Origins of the Old Timer’s Game

The Old Timers Game was born in the 1970s from the mind of Jack Cahill, owner of The Harbor Inn. 

Before sports bars were invented, there was one TV in Harbor Inn, and it got two channels. In the fall, a Giants game was on every Sunday afternoon, and the Yankees, Mets, and Red Sox dominated the summer. Red Sox legend, Hall of Famer Carl Yastrzemski grew up in Bridgehampton, and more than one patron of Harbor Inn played against him when Bridgehampton met Shelter Island in high school baseball.

When Jack heard that the Little League team needed more support, he put together a baseball team, the “Over the Hill Gang” pitted them against a team organized by Dick Edwards who owned The Dory and made it into an annual event. Starting in the 70s, on the third weekend in September, the annual Dory vs. Harbor Inn baseball game raised money for the Little League for decades.

Charlie Beckwith was a player and fundraiser for the Old Timers game in the 70s, when he worked weekends at The Harbor Inn as a bartender. He remembered when the games attracted large crowds. “Some started putting quite a bit of money in, people that could well afford it,” he said. 

Charlie organized a Little League trip to Shea Stadium for a game. “I had gotten a deal for really cheap tickets, but we didn’t have any money for the buses. A guy who used to live out here asked how much we needed. He opened his wallet, counted out $400 and said, “Make sure every kid gets a program.”