[2] After returning to Maine, he started a business renting out golf carts on Peaks Island, where he lives.
In 2016, Sylvester ran to succeed the term-limited state representative for the 39th District, Diane Russell, defeating lawyer Andrew Edwards in the Democratic primary and Republican Peter Doyle in the general election.
[4] Sylvester ran as an open democratic socialist, supporting an increase in the minimum wage, legalization of marijuana, and single-payer health care.
Bills sponsored by Sylvester to create a municipal “union card check” law and to create a Ground Water Resource Committee were signed into law while a bill to allow teachers to bargain over preparatory periods was vetoed by Governor Janet Mills.
Sylvester sponsored bills to allow public sector workers the right to strike and to create a state-wide single payer healthcare system.