Destiny and a Dream: Bobby Checchi’s Last Trip to Yankee Stadium 

Bobby and Gavin Checchi. Submitted photo

In August 2010, Bobby Checchi was in the hospital fighting a rare form of cancer when his family conspired to make a birthday wish come true for the longtime New York Yankees fan. 

They reached out to the team, asking if the Yankees could arrange a visit to Yankee Stadium for Checchi, a popular Sleepy Hollow Police detective and Tarrytown Schools SRO who was by then wheelchair bound. 

What unfolded after that is captured in The Last Home Run, a documentary directed and edited by his son, Gavin Checchi, which recently won the Audience Choice Award at YoFiFest in Yonkers.

The 10-minute film, which uses on-screen interviews with Gavin and his mother, Nancy Checchi, plus illustrations and photographs, is a moving tribute to Bobby Checchi, whose love of baseball is legendary in his hometown. 

The Checchis’ wish was fulfilled by manager Joe Girardi, who put together a 60th birthday for Bobby that can only be described as a Yankee fan’s dream, including wearing the skipper’s World Series rings as he and his family watched the Aug. 4, 2010, game against the Toronto Blue Jays from box seats.  

Right on cue, Yankee third baseman Alex Rodriguez blasted his 600th home run in the first inning, a fitting coda for Bobby Checchi, who was at the old Yankee Stadium on his 50th birthday when A-Rod clubbed his 500th round-tripper. 

Gavin Checchi in the short film, The Last Home Run, about his father, Bobby’s memorable trip to Yankee Stadium. Submitted photo

Bobby Checchi’s passion for baseball extended well beyond his Yankees fandom. He was a volunteer assistant coach for the varsity and junior varsity baseball teams at Sleepy Hollow High School, and developed the summer and fall programs for the TNT Baseball Softball Association.  

Gavin Checchi in the short film, The Last Home Run, looking at the jersey his father, Bobby, received from Joe Girardi during a memorable trip to Yankee Stadium. Submitted photo

Following his death in 2011, a scholarship at Sleepy Hollow High School funded by donations from the Yankees and community members was established in Bobby Checchi’s name for students pursuing criminal justice studies.  

“I think it was part of my dad’s destiny to have that special day with his family,” Gavin Checchi says in the film. 

He adds: “I think what it meant for my dad was that dreams can come true. I think that my dad, he probably never thought in the beginning that he’d be able to have the opportunity to go to Yankee Stadium on that day, but you never know, that’s the whole thing about life.” 

Gavin Checchi, now 23 and living in Beacon, studied filmmaking at Recording Radio Film Connection, where he was mentored by Zef Cota of Alphabet City Films, who encouraged Gavin to enter The Last Home Run in festival competition. 

The documentary has been submitted to multiple festivals and will be shown Feb 18 during a winter film series at RVE Warehouse District, 883 Broadway and North Ferry Street, in Albany. 

Click here to watch the trailer for Gavin Checchi’s film, The Last Home Run. 


1 Comment

  1. Love this, Gavin!!! Congratulations on your Audience Choice Award, what a beautiful tribute to you Dad and a wonderful reminder to us all how dreams can come true. Bravo!

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About the Author: Robert Brum