Scott Jennings started his political career licking envelopes in a campaign office but went on to work for campaigns at both the local and national level, including four presidential campaigns. The CNN senior conservative political commentator – and keynote speaker at NAIOP’s 2025 Chapter Leadership and Legislative Retreat – joins the podcast to share his views on political strategy, including what it takes today for a candidate to win, the two policy areas he believes drove Donald Trump back into the White House, and how Republicans “completely revolutionized” their ground game in the 2024 presidential election. He discusses the ambitious timeline for Congress to pass a tax bill, the Trump administration’s use of tariffs and other economic levers, whether J.D. Vance gets the nod as the Republican candidate for 2028, and even his opinion on the Democratic Party’s best option for a candidate in 2028. Recorded on March 18, 2025.