The Mr. Midwest Leather Contest first began in 2005.  The contest was founded by Kurt Pierce.  The first Mr. Midwest Contest was held at One Flight Up in Dubuque, Iowa.  The 1st Mr. Midwest titleholder was Wes Kassulke.  Mr. Midwest Leather 2005 went on to place in the top 20 at IML.

The following year the Contest was held in Chicago, Illinois at the Eagle.  The Midwest Leather Contest 2006 boasted the largest number of contestants of any leather contest in the United States leading up to IML that year.  Dr. Bruce Karmazin was named Mr. Midwest 2006, and also placed in the top 20 at IML.

In 2007, the contest moved to St. Louis, Missouri.  The contest was held at JJ's Clubhouse & Bar.  Dave Drees was chosen at Mr. Midwest 2007, and was noted for creating the Clean and Sober Leather Chat as well as remarkable fundraising.

The Mr. Midwest Leather Contest 2008 will be held again in St. Louis, Missouri at JJ's Clubhouse & Bar on April 4, 5, and 6.  The contest is open to contestants throughout the Midwest region including the 13 states: Illinois, Iowa, Wisconsin, Indiana, Missouri, Minnesota, Michigan, Ohio, North Dakota, South Dakota, Kansas, Nebraska, and Kentucky.

 
Mr Midwest Leather 2007, Dave Drees (Left)
with Mr. Midwest Leather 2006, Bruce Karmazin