The Chris Mattingly Award for Outstanding Leadership in Kentucky was established to honor the memory of one of the first McConnell Scholars. Chris died as a result of a car accident on November 1, 1996; he was 21 years old. He had completed 104 hours towards a Bachelor of Arts degree in Political Science at the University of Louisville. Chris was a member of the first McConnell Leadership Council; he was also the communication coordinator for the Scholars.

The Chris Mattingly Award was first presented in 1998 and is given annually at the Senior Dinner to an individual who reflects exceptional character and leadership benefiting the Commonwealth of Kentucky. McConnell Scholars vote on this award. To date, eleven individuals have received the Chris Mattingly Award for Outstanding Leadership in Kentucky, with Crusade For Children CEO, Rebecca Jackson as the most recent award winner.