This scenario isn't entirely impossible. For the 2016 election, FiveThirtyEight ran simulations of election results based on polling, and there were some simulations (roughly 1-2%) which produced a Democratic win of the EC without winning the PV.
It's difficult to make up such a scenario, but with Booker on the ticket, they both could win some Southern states that Hillary didn't win and some Western states, while the Inner South and the Great Lakes states and Florida keep on trending Republican due to alienation.
