Chilly Willy debuted in Extreme Championship Wrestling in early 2000, defeating Scott D'Amore in Toledo, Ohio on February 25, although he later lost matches to The Prodigy and HC Loc on ECW on TNN during the next several weeks. After defeating Johnny Swinger on March 24, he began feuding with Swinger over the next few months.
In his first pay-per-view appearance, he defeated Johnny Swinger at Wrestlepalooza 2000 in St. Louis, Missouri on April 16. He would face Swinger in a rematch the following month, defeating him at Hardcore Heaven 2000 in Milwaukee, Wisconsin on May 14. During the "Midwest Massacre" tour, he would also score victories over Tony DeVito and E.Z. Money in June.
With Chris Chetti and Nova, Willy beat the F.B.I. (Little Guido, Sal E. Graziano and Tony Mamaluke) in Wichita, Kansas on July 1, 2000. Several days later, they defeated the F.B.I. in a rematch on ECW on TNN in Poughkeepsie, New York on July 7. Losing to ECW TV Champion Rhino on ECW on TNN later that month in Peoria, Illinois, he teamed with The Sandman to defeat the F.B.I. (Little Guido and Tony Mamaluke) in Huntington, West Virginia on August 4, when Willy pinned Mamaluke. In the following weeks, they also defeated Justin Credible and Rhino several times before losing to them in the opening rounds of a championship tournament for the vacant ECW World Tag Team Championship in Manhattan, New York on August 25.
Teaming with The Sandman against The Baldies (Tony DeVito and Angel), Willy teamed with Mikey Whipwreck and Balls Mahoney to defeat Johnny Swinger, Simon Diamond and C.W. Anderson in a 6-man tag team match in Buffalo, New York on September 8. The following night on ECW on TNN, he and Balls Mahoney defeated The Baldies in Mississauga, Ontario.
Feuding with The Baldies over the next several weeks, he and Mahoney were defeated by The Baldies in a tag team match at Anarchy Rulz 2000 on October 1 and, with The Sandman and New Jack, defeated Justin Credible and The Baldies on October 12. The following month, he and Mahoney defeated The Baldies in a rematch at November to Remember 2000 on November 5 in a flaming tables match. During the next two months, he also defeated Tony DeVito and Mike Bell in singles matches. At ECW Guilty as Charged 2001, Balls Mahoney and Chill Willy fought Simon Diamond and Swinger to a no-contest because Rhyno attacked all four wrestlers. This was Willy's last ECW appearance.