T. Milton Street was raised on a farm in Montgomery County in a Seventh-Day Adventist Church family. He and his brother, former Mayor John Street, earned their political stripes as young men when they fought for human rights issues in the 1970s.

Both Streets went on to notable careers in public office. Milton Street's ended after he aided Republicans in their takeover of the Pennsylvania Senate in 1980. He lost his 1984 re-election attempt due to voter backlash.

Public attention continued for the next three decades. He entered into wide-ranging business ventures throughout Philadelphia, and ran for City Council in 2007 even though his nephew, Sharif Street, was already in the race. Street was later arrested and served time in federal prison for failing to pay income taxes on $3 million.