Jennings grew up in Phoenix, Maryland. As a child he was an active 4-Her, raising market lambs and cattle and showing them at various fairs including the Maryland State Fair. At the age of sixteen he joined the Jacksonville Volunteer Fire Company, Station 47, where he was a firefighter and emergency medical technician. He eventually became a lieutenant before serving on the board of directors. In 1994 he, and several other firefighters from Maryland, were sent to Idaho to fight wildfires that were raging due to extreme drought. They received recognition from Maryland Governor William Donald Schaefer for their actions. He is a graduate of Baltimore County Public Schools. Jennings attended Carrol Manor Elementary School, Cockeysville Middle School and graduated from Dulaney High School. After graduation, he attended Essex Community College, where he graduated and received his A.A. in 1995. Jennings then transferred to the University of Baltimore, where he graduated in 1997 with his B.S. in Business Administration. While in college, he worked at the United States Capitol for Congressman Robert Ehrlich as a staff assistant. In 1998, Jennings became co-owner and president of a feed store in Hereford, Maryland, The Maryland Feed Company. In 2007, he merged The Maryland Feed Company with The Mill to create The Mill of Hereford. Jennings has been farmer since his days in 4-H. While in college he worked on a dairy farm before starting his own beef cattle farm where he raises Black Angus. He married Michelle Slusher in 2004. Jennings is an instrument rated pilot. He has served in the Maryland Air National Guard with the 135th Airlift Squadron since 2008. He is a loadmaster having initially trained on the C-130 before transitioning to the C-27J Spartan. In 2012 he transferred to the 276th Cyberspace Operations Squadron. He was activated and deployed during the 2015 Baltimore protests and riots.
House
Since his election to the House of Delegates, Jennings has been very active in environmental and agricultural issues. He served on Environmental Matters Committee, the Agriculture Preservation & Open Space subcommittee, the Wetlands & Waterways Funding Work Group in 2004, and the Natural Resources subcommittee in 2006. Jennings was the chair of the Natural Resources work group in 2004, was a member of the Agricultural Stewardship Commission from 2005 to 2006, and has been a member of the Maryland Fire, Rescue and EMS Caucus since 2003. He has also been on the Maryland Rural Caucus and the Maryland Legislative Sportsmen's Caucus since 2003. His efforts were recognized when he was selected as Deputy Minority Whip.
Legislative notes
voted against the Healthy Air Act in 2006
voted for slots in 2005
voted against in-state tuition for illegal immigrants in 2007
Senate
Jennings was elected to the Maryland Senate in 2010, and served on the Education, Health and Environmental Affairs Committee, Joint Advisory Committee on Legislative Data Systems, and Joint Committee on Transparency and Open Government. He was appointed as the Senate's Minority Leader in 2014 and won reelection that year. Since 2015, Jennings has served on the Finance Committee, Legislative Policy Committee, the Joint Committee on Legislative Information Technology and Open Government, the Joint Committee on Spending Affordability, and the Public Safety and Policing Work Group. In 2016, he joined the Executive Nominations Committee.