Prior to entering politics he worked in a sugar refinery and was an electrician's helper.

In 1975 he led a successful fight against Governor Michael Dukakis bid to eliminate the council.

Skinner, as assistant attorney general, had prosecuted several of McDonough's fellow councilor for extortion.

[1] McDonough was a candidate for Governor of Massachusetts in 1954 and 1956, but lost the Democratic nomination at the party's convention both times.

Prior to running for Mayor, McDonough left the liquor business and went into insurance.