Freeport, New York holds a surprisingly rich and unique place in the history of professional wrestling. From legendary icons of the past to present-day champions, Freeport has been a consistent backdrop for the evolution of sports entertainment.
In the earlier days of professional wrestling, Freeport High School served as a venue for the World Wide Wrestling Federation (WWWF) and World Wrestling Federation (WWF), the precursor to the modern WWE. The school gymnasium is documented to have hosted non-televised events in the 1970s and 1980s featuring the likes of Rocky Johnson (father of Dwayne "The Rock" Johnson), Tony Atlas, Afa, Sika (father of Roman Reigns), Special Delivery Jones, Chief Jay Strongbow, and Ivan Putski. More information on these cards can be found here and here.
On a larger scale, Freeport Stadium is documented to have hosted live boxing and professional wrestling events in the 1930s (via Jack Curley Promotions), 1950s (under NWA Capitol Wrestling), 1960s and 1970s featuring the likes of Bruno Sammartino, George "The Animal" Steele, Eddie Graham, Jimmy Valiant, Karl Gotch, Antonino Rocca, Captain Lou Albano, "Nature Boy" Buddy Rogers, Arnold Skaaland, Haystacks Calhoun, Dr. Jerry Graham (reportedly Vince McMahon's favorite wrestlers as a child), and Gorilla Monsoon.
As contributed by reader Mailman Nick and verified from a New York Times article, Jess McMahon -- grandfather to Vincent Kennedy McMahon, WWE chairman, and father of WWWF founder Vince McMahon Sr. -- had his first event as a live event promoter at Freeport Stadium in 1932. The card included Cy Williams (former New York Giants' football star), "Dr. Ralph Wilson of Philadelphia," Vanka Zelezniak and Joe De Vito. More about Freeport Stadium and its previous boxing and wrestling events can be read here, here, here, here, here, here, here, here, here and here.
During the 1990s, Freeport once again found itself in the wrestling spotlight, this time courtesy of Extreme Championship Wrestling (ECW). The Freeport Recreation Center multiple ECW events in 1998 and 1999, bringing the brand’s gritty, hardcore style to a new audience. Wrestlers like Taz, Rob Van Dam, Sabu, Yoshihiro Tajiri, Bubba Ray Dudley, Tommy Dreamer, Tracy Smothers, Lance Storm, Jerry Lynn and The Sandman plied their violent craft into this small venue -- generally called "the rec center" by locals -- further establishing ECW’s renegade reputation. More information on these events can be found here, here and here.
The village's wrestling connection continues into the modern era. In 2018, a NYWC event was held at Tropix which included former WWE Tag Team Champion Mike Mondo on the card. In 2025, Freeport’s iconic Nautical Mile hosted a National Wrestling Alliance (NWA)-sanctioned event that drew notable talent from across the industry. Headlined by NWA World’s Heavyweight Champion Tom Latimer and NWA Women’s Champion Kenzie Paige, the show also featured high-profile stars such as Natalia Markova, local favorite Joe Ocasio, Patrick Fitzpatrick, and Aron Stevens (better known to WWE fans as former tag team champion Damien Sandow). This event symbolized a return to intimate, open-air wrestling spectacles and highlighted Freeport’s ongoing relevance in the wrestling world.
Adding a personal connection to this wrestling tapestry is Sgt. Craig Pittman, a former WCW star and U.S. Marine Corps veteran who hails from Freeport. Known for his no-nonsense style and amateur wrestling background, Pittman represented his hometown with pride on national television in the 1990s. He reportedly made his televised debut as one of the judges for a "Marquess of Queensberry Rules" match between Ric Flair and Lord Steven Regal on the April 30, 1995 episode of Worldwide. Pittman is believed to have made his pay-per-view debut at The Great American Bash that same year, against "Hacksaw" Jim Duggan.
Freeport is also often credited as the hometown of Rock & Roll Hall Of Fame artist Flavor Flav, who has served as a guest General Manager on WWE's Monday Night Raw program. WWE online content featuring Flav can be seen here.
Altogether, Freeport’s enduring relationship with professional wrestling illustrates how even small towns can play big roles in the industry. From Bruno Sammartino’s appearances, to ECW’s anarchic shows, to having a hometown WCW star in Sgt. Craig Pittman, to the NWA’s 2025 resurgence, the village has embraced every era of the sport. Its venues, crowds, and athletes have all contributed to a quietly significant wrestling history that continues to unfold along the shores of Long Island.
Researched by Darren Paltrowitz on June 4, 2025. Updated on June 14, 2025 and June 18, 2025.