Jon Lieb’s Legacy of Sportsmanship, Community Spirit Lives On in Pleasantville’s Annual Softball Tribute

By Toby Rosewater

For anyone who attended Pleasantville High School baseball games last season, a new, roughly 20-foot-high structure was hard to miss. 

Outfitted with wheels, white scaffolding, and a robust sound system, the glistening new press box sang over the baseball diamond during all 13 home games. 

Partially funded using proceeds from the inaugural Jon Lieb Memorial Softball Tournament, it is a physical embodiment of Lieb’s legacy. 

Throughout his 53 years of life, Lieb was known as a huge sportsman. He founded his own softball team, The Moonlight Grahams, announced high school baseball games (from a folding table), and rallied the community around local athletics — always eager to connect with friends and strangers. 

Yet, even as he thrived publicly, Lieb silently struggled with private pain. He died by suicide in June of 2023. 

“My husband was the last person you’d ever expect to do that,” his wife Sarah Lieb told The Examiner in an interview last week. “He was so full of life, almost like the mayor of Pleasantville. It was a shock to everyone.”

This year’s second annual Jon Lieb Memorial Softball Tournament, set for Sunday, June 22, from 11 a.m. to 3 p.m. at Parkway Field in Pleasantville, brings the community together to honor Lieb’s spirit.

More Than a Game

Following his death, Sarah founded The Jon Lieb Legacy Fund in partnership with Break The Hold, a local organization focused on mental health and suicide prevention. From there, friends and family conceived the Jon Lieb Memorial Softball Tournament — a fundraiser envisioned as both a tribute to Lieb’s love of the game and his passion for community. 

The inaugural tournament last June was a huge success. 

“It was incredible,” Sarah said. “We had like a hundred people show up.”

Eight teams played from 9 a.m. to 3 p.m. as friends and family, on picnic blankets and lawn chairs, watched softballs flutter across the sprawling summer sky. In the end, the tournament raised $1,500 for the Jon Lieb Legacy Fund and $1,000 for Break the Hold.

“It was a tremendous success, but we hope to improve it this year,” said Paul Dispenza, Jon Lieb’s close friend and the event’s main organizer. 

Last year, food trucks catered to the lunchtime crowd. This year, alongside an ice cream truck, they’re hosting the Taco Project. Additionally, Dispenza plans to use the mobile press box (and its microphone) for announcements. 

“We’re thinking about maybe having cornhole, too,” added Dispenza. “maybe even like a home run contest eventually, but these are all larger goals.”

‘Sportsmanship, Friendship, and Love’

This June marks two years since Lieb’s passing, and as friends and family move further from their grief, the tone of the event may feel different, too.

Last year, beyond being a community event, the tournament served as a kind of physical eulogy. 

Jon and Sarah’s college-aged children led a heartfelt tribute by releasing balloons on first base.

“That was Jon’s position,” Sarah explained. “So that was… very touching and nice.”

And, as Sarah also noted, the event helps ensure the community will continue to remember “who Jon Lieb was.”

It’s often said that every person dies twice — once when they take their last breath, and again when their name is spoken for the last time. Through softball, the press box, and the lasting memories of friends and family, Jon Lieb still remains — and will always remain — very much alive.

“His character,” Sarah concluded, “continues to persevere throughout our Pleasantville town, you know, through sportsmanship, friendship, and love.”

Teams interested in playing can contact Dispenza at 914-671-1085.