After assisting George W. Bush with both his 2000 and 2004 presidential campaigns, Jennings was appointed Bush's Deputy Director of Political Affairs and Special Assistant to the President.
While attending the University of Louisville, he worked for the local WHAS Radio station.
He was the political director for Ernie Fletcher's 2003 Kentucky gubernatorial campaign.
He was born and raised in Dawson Springs, Kentucky.
Jennings assisted fellow Kentucky Republican Mitch McConnell with his successful 2002 Senate re-election campaign.