Dates: December 26, 27, 28, 30, 31
Admission: $5 (reentry requires an additional $5 admission.)
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Jack Tosh came to York as an Assistant Director of Administration in 1974 and became Athletic Director in 1975. He was York's Athletic Director of 18 years. During that time, Jack was also an assistant basketball, football and baseball coach; as well as a varsity golf coach. Jack started the York Turkey Tournament, the York Holiday Tournament and the York Holiday Festival. The York Holiday Festival was renamed the Jack Tosh Holiday Classic in 1990. 

While Jack was AD, York teams won 61 West Suburban Conference Championships, 68 Regionals, 38 Sectionals, and 10 State Titles, including the 1984 IHSA Girls AA State Basketball Championship. Jack was the President of the Inter-Suburban Basketball Association and was elected into the Illinois Basketball Coaches Association Hall of Fame in 1989. Jack retired in 1990 and received the 2001 Buzzy O'Connor Award, the IHSA's highest award.

In 2013, Vince Doran continued to build the Jack Tosh Holiday Classic into a special event by expanding the field to 32 teams. The Jack Tosh has turned into a five day event that comprises of 67 games. The event has 16 games being played in two gyms over the first four days and then has three games on the final day. The Jack Tosh continues to grow each year in the way that it is carried out and it continues to build upon the original vision of Jack Tosh for 50 years