The family returned to Kingston and he started pre-school there before moving to Saint Ann Parish where his father took up a new job as principal of Moneague Teachers' College.

Phillips first entered parliament as an appointed senator after the People's National Party won the 1989 general elections.

He remained in post until 1994, when he was elected to parliament as the member for Saint Andrew East Central.

Simpson-Miller also named him Deputy Prime Minister in an apparent attempt at party unity.

In the 2020 Jamaican general election, he was defeated by current Prime Minister, Andrew Holness, by a 49-14 seat margin.

[4] He resigned as Opposition Leader and PNP President after the defeat, triggering the 2020 People's National Party leadership election.