At Michigan, Matheny co-captained the Wolverines baseball team. Matheny's defensive and throwing skills had drawn the notice of major league scouts, and the Toronto Blue Jays drafted him in the 31st round of the 1988 Major League Baseball Draft. They waited two days until after the draft ended to tell him of his selection, and initially refused to disclose which round they had selected him in. Two days before he was due to attend his first class at Michigan, Blue Jays general manager Pat Gillick appeared at Matheny's home to convince him to sign. Gillick was ready to offer a deal normally reserved for second-round picks. At the time, teams held the right to negotiate with their draft picks until the moment they entered their first classroom in the following academic year. The Blue Jays called Matheny frequently until the morning of his first class, hoping he would sign. However, Matheny was convinced that he would not be a very good professional player at that point, so he chose to attend college instead. Before proceeding to his first class, he called the Blue Jays from his dormitory room to inform them of his decision. Matheny was a member of the 1989 Connie Mack championship team. In 1990, he played collegiate summer baseball with the Cotuit Kettleers of the Cape Cod Baseball League and was named a league all-star. Playing career (1991–2006) Minor leagues, Milwaukee Brewers and Toronto Blue Jays (1991–99) The Milwaukee Brewers selected Matheny in the eighth round of the 1991 Major League Baseball Draft, and he spent three years climbing the minor league system. He made his major league debut with the Brewers on April 7, 1994, at the age of 23; he became their starting catcher early in the next season. During a game against the Pittsburgh Pirates on May 26, 1998, Matheny was batting in the bottom of the ninth when he took a pitch from Rich Loiselle off his face. Remaining upright, Matheny placed his hand on his hip as Pirates catcher Jason Kendall and home plate umpire Jerry Crawford motioned wildly for the Brewers trainers. He spat out a mouthful of blood as he walked off the field. At the end of that season, he became eligible for salary arbitration and the Brewers granted him free agency a few months later. Ten years after they drafted him, the Toronto Blue Jays signed him on