Return of The Glory Cup: Football, Pranks and A Neighborly Rivalry

The series between the Shorewood and Whitefish Bay football teams dates back to the 1930s and was notorious for student pranks.

Friday night, in the WIAA Division 2 playoffs, Whitefish Bay and Shorewood will play football against each other for the first time in 11 years.

The programs have had little in common recently, playing in dramatically different leagues and experiencing different levels of success. Even Shorewood’s name has changed after forming a co-op with Messmer. 

So it’s easy to forget these two neighboring schools played 67 consecutive years for The Glory Cup, a rivalry marked by pranks so rampant that schools took to leaving stadium lights on overnight during the week and stationing police officers on rooftops.

“I think a lot of the Shorewood kids thought Whitefish Bay was snobby and was full of rich kids, and a few of the Whitefish Bay kids had it in their head that Shorewood kids were east side scrubs,” said Steve Whitcomb, a former Whitefish Bay player. “I think it was because we were so close to each other and we would see each other at church and on the sidewalks. The rivalry was really more fun than heated. It was generally good natured.”

The prize

"The Glory Cup," the neighborly rivalry between Shorewood and Whitefish Bay, dates back to 1934 and was held every year until 2001. In the early years of the rivalry, it was competitive. The two teams split the first 30 years, with 15 wins apiece. But Whitefish Bay has since dominated the series, winning the last 17 games and owning the series 45 wins to Shorewood’s 22. Shorewood did not score in eight of the last 13 meetings.

A dated trophy and plaque still reside in the trophy cases outside of the Whitefish Bay Field House.

A car in the pool?

A 1981 article in the Milwaukee Journal noted that administrators on both schools were on high alert for the game. The schools stationed police officers on the rooftops outside of the stadium, and school officials checked students at the gates for eggs, tomatoes and other possible projectiles. As preventive measures, school officials kept the field lights on overnight and asked local businesses not to sell eggs or tomatoes to students on game day, according to the article.

Shorewood High School alum Greg Trost remembered a story where students disassembled a Volkswagen Bug and reassembled it in the Whitefish Bay pool.

"The VW story is from the late ’60s and I have it from reliable sources that it happened," he said.

Another tale has a student throwing red paint onto a statue on the Whitefish Bay High School campus, being caught and forced to clean it during school hours.

"I remember dances in the youth center or Bay gym after," said Tamara Finely-Williams. "And, the late night sneaks to pull pranks on WFB. Such good times."

Luke Gaskell, a 1993 Shorewood alum, said someone in his class "borrowed" the Glory Cup during his senior year and presented it to the principal with a card that said something to the effect of, "Since we couldn't win it for you, we thought we'd steal it"

In 1976, the pranks got a little more serious. In that year, a Shorewood kid broke into the Whitefish Bay football field and axed the power lines, delaying the start of The Glory Cup game.

“We had to sit in the locker room for an hour or two twiddling our thumbs, and eventually a bus came and brought us down to Shorewood to play the game,” Whitcomb said. “It was about 9 p.m. at that point, and I think we ended up losing.”

The rivalry between the schools was less about football and more about the rivalry between the two small villages, Whitcomb said.

Gerry Kasik, who has been in charge of disciplining students at Whitefish Bay football games for decades, said she remembers pranks being played between the two schools. Regardless, she said she always looked forward to The Glory Cup, and is happy to see the two teams play again Friday night.

"It was always fun to watch every year so it was sad when it ended," she said.


The Shorewood football program has changed substantially since the Glory Cup ended. During the 1990s Shorewood had a 63-game losing streak, one of the longest in national prep history. Since then the school started the co-op with Messmer, joined a conference comprised primarily of small, private schools and now has made the playoffs twice in a row under coach Drake Zortman.

"We have been able to really progress and grow as a team," Shorewood Athletic Director Bill Haury said. "Right now, we are where we are supposed to be."

There's interest in renewing the age-old rivalry, at least in Shorewood, Haury said.

"There was talk at one time of making it a soccer rivalry," he said. "But our side, we would like to renew the (football) rivalry."

He said when Shorewood-Messmer closed out the regular season this year, they knew they would draw Whitefish Bay, and it would get folks in both villages talking about the glory days of The Glory Cup.

Unfortunately, the trophy will not be at stake in Friday’s contest. Under WIAA rules, there can't be an added incentive in a playoff game, Haury said. If the two schools agreed to re-establish the annual competition, it would have to be a regular season, non-conference game.

Shorewood-Messmer will do battle with the Blue Dukes at 7 p.m. Friday at Whitefish Bay High School.


Glory Cup scores (Whitefish Bay-Shorewood)

1934 7-6 1949 26-14 1964 34-7 1978 43-6 1993 28-6 1935 0-19 1950 13-7 1965 52-13 1979 35-6 1994 41-0 1936 6-38 1951 7-20 1966 32-13 1980 21-13 1997 38-20 1937 7-6 1952 25-0 1967 7-12 1981 9-12 1998 56-6 1938 15-13 1953 12-6 1968 7-16 1982 6-30 1999 56-6 1939 9-6 1954 32-0 1969 7-13 1983 33-0 2000 38-0 1940 6-7 1955 12-13 1970 14-21 1984 14-6 2001 64-0 1941 15-21 1956 16-0 1971 13-7 1985 21-14 1942 0-6 1957 0-19 1972 22-8 1986 22-12 1943 13-21 1958 18-24 1973 22-6 1987 33-0 1944 7-13 1959 7-47 1974 15-8 1988 21-0 1945 25-7 1960 7-14 1975 7-12 1989 28-0 1946 14-34 1961 13-6 1976 28-14 1990 35-0 1947 6-19 1962 25-0 1977 6-0 1991 70-0 1948 26-0 1963 7-6 1977 6-0 1992 32-26
Bob McBride October 18, 2012 at 12:40 PM
i remember the egg fights and having to scrub down parents' cars that got pummeled with them. I think I remember a Volkswagon hanging OVER the pool by the rafters in the '70s but I don't remember one ever being disassembled and reassembled IN the pool. I'm not sure how you could do that, since there was only one pool for most of the '60s and it was in the basement of the HS.
Anne Elliot October 18, 2012 at 03:40 PM
In my senior year a group of Shorewood students snuck into the beautiful new Whitefish Bay pool with minnows which pretty promptly died leaving a stench throughout the school the next day. As I met Whitefish Bay students through the years at UW and even in NYC they all remembered that prank with grudging respect.
Bob McBride October 18, 2012 at 05:33 PM
I was in one of the first gym classes of the day the day after and part of what we did was fish the minnows out of the pool (I think the first class of the day had the worst of it. We just caught the stragglers). Honestly, it didn't stink all that bad. Then again, we had all just come out of the boys locker room prior to hitting the pool...


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