[citation needed] In May 2000, Jennings was named Vice President of Business Development for Givenation.com, a non-profit organization run by former Democratic National Committee Chairman Steve Grossman.
He also became a partner in the Red Mango Frozen Yogurt store at the Maine Mall and a development at Thompson's Point, a project for which he requested and received a $31 million, 30-year tax break from the City of Portland.
At the time of his hiring, Dan Boxer, an adjunct professor at the University of Maine School of Law, raised questions about a potential conflict of interest between Jennings's role as a partner in the Thompson's Point project, located in Portland, and his responsibilities as South Portland City Manager, which included attracting businesses that could potentially compete with his Thompson's Point project.
1 for progressives," as Jennings pushed for the closure of the India Street Health Clinic, ending general assistance for asylum-seekers, limiting access to the city's homeless shelters, against a $64 million municipal bond to renovate elementary schools, and against the city's passage of the nation's toughest pesticide ban mandating organic lawn management which when passed over his objections he underfunded.
[16] Jennings had long-running feud with elected Portland Mayor Ethan Strimling and faced sharp criticism from local Black Lives Matter activists, who in 2020 called for him to be fired.
[22] In December 2021, Jennings met with Church of Scientology leader David Miscavige, who has stirred controversy by purchasing extensive real estate in downtown, much of which sits vacant.