Bollinger was born on 15 th November 1979, to Rob and Lisa in the Capital City before sailing on the clouds of stardom, at Grand Forks Central and then with the Badgers. H e did his major in history from the University of Wisconsin where he also played football as a quarterback . His father, Rob was an offensive coordinator at North Dakota . Bollinger also became the guest speaker at the annual athletic banquet at the Bismarck Elks Club. In 2000, Los Angeles Dodgers baseball organization signed him.

As a collegiate, he finished his career as one of the leading quarterback in Wisconsin history. He was red-shirted as a Badger in his first year and became the starter as a freshman, early in his second year. He is considered as the only Big Ten quarterback to wins games at Ohio State and Penn State in the same season. He also made to the state title game in football, basketball, and baseball.

In 2004, Bollinger turned the ball over twice and sprained his right knee in the opening playoff for the Jets.