The WIAA goes back to 1925 to determine the beginning of its boys swimming tournament program. The first meet was held at the University of Wisconsin in Madison. The meet was held indoors, according to WIAA records, because "water on the lake was too rough.''
Milwaukee West won the first championship with West Allis runner-up.
The meet was held at a variety of sites through the years, but since 1966, it has been held exclusively at UW-Madison.
Madison Memorial has won 16 team championships to lead all other programs. Ten of Memorial's titles have come in the last 12 years. The Spartans also have 16 runner-up finishes. Waukesha (before it became North, South, and West) won 15 State championships, which is second-most among all schools. Seven of those titles came in succession (1964-70). All but one came during a 17-year period from 1958-1974. Madison West has won 13 State team titles. Wauwatosa, before it became two schools with East and West, won nine titles. Seven of those came during an eight-year period from 1944-51. Shorewood also has nine titles, including five in a row from 1935-39 and all nine of them coming from 1933-1943. Arrowhead and McFarland have won six team championships, with all six of McFarland's coming consecutively from 2007-12. Kenosha and Whitefish Bay have won five titles.
Boys swimming and diving was conducted in a single class until 1993 when a two-division format was adopted. Verona won the first Division 2 team championship.
Only five athletes have won the same individual event four times. Kyle Bubolz of Waukesha North/Kettle Moraine was the first to do it. He won the Division 1 50-yard freestyle from 2001-04. Ryan Jefferson of Edgewood accomplished the feat in the diving competition, winning the Division 2 titles from 2003-06. Alex DeLakis of Eau Claire Memorial/North was a four-time Division 1 champion in the 100 breaststroke from 2010-13. In 2015, Joe Kaszubowski of Whitefish Bay was the fourth individual to accomplish the feat, capturing his fourth title in the Division 2 diving competition. Paul DeLakis of Eau Claire Memorial/North joined the ranks of the group when he won his fourth straight 100 breaststroke title in Division 1 in 2017.
There have been 40 three-time winners in the same individual event. Of those, only four individuals have won three titles in two different individual events. John Thuerer of Rhinelander won three titles in the 200 and 400 freestyles; both Edward Garst of Wauwatosa and Tom Wanezek of Brookfield East won three titles in the 50 and 100 freestyles; Tom Shane of New Berlin Eisenhower won three 200 individual medleys and 100 butterflies; and Ben McDade of Monona Grove has won a trio of championships in the 200 and 500 freestyles from 2015-17 and has the opportunity to go for his fourth straight in those events in 2018.
Ryan O'Donnell of McFarland has won the most titles, including relays, with 14. Ben McDade of Monona Grove has won 11, while Ben Anderson of Arrowhead, Jay Mortenson of Madison West and Tom Wanezek of Brookfield East have won 10. Paul DeLakis of Eau Claire Memorial/North and Chris Richard of Sturgeon Bay/Southern Door have won nine titles.
Madison Memorial has won the most State event titles with 89, Waukesha, before it split into three schools, recorded 77 individual and relay championships. Madison West has had 64 champions. Wauwatosa crowned 61 champs before forming separate programs.
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