Winnecke graduated from Central High School in 1978 and attended the University of Evansville where he received a Bachelor's degree in communications.

For thirteen years prior to running for mayor, he worked as senior vice president and marketing director for Fifth Third Bank.

[3] Winnecke has held office continuously since shortly after the 1999 city campaign, when he was selected in a GOP caucus to succeed then-newly elected Mayor Russ Lloyd Jr., on the Vanderburgh County Council.

As a county official on both the council and the commissioners he balanced budgets for 11 straight years and held per capita spending to 43% below the state average.

In his first year in office he fought for, and secured, a state-funded full cloverleaf at one of the city's busiest intersections at the Lloyd Expressway and U.S. Route 41.

He successfully championed a downtown location for a new interdisciplinary academic health science education and research campus affiliated with the Indiana University School of Medicine - Evansville.