Prior to the founding of the New Democratic Party, in 1939, the CCF (Cooperative Commonwealth Federation) began to challenge the long-standing two-party system of politics in Nova Scotia.  From 1939 until 1967, CCF candidates made gradual inroads electorally in Halifax. Candidates such as Charles Moulton (Halifax North, 1961 – 1466 votes) and Harold Martell (Halifax West, 1961 – 1225 votes), while not being elected, clearly showed support for a left-leaning agenda in the city.

With the founding of the NDP in 1967, from a coalition of the CLC (Canadian Labour Congress) and the CCF (Cooperative Commonwealth Federation), a new era in electoral politics here in Nova Scotia and in Halifax was launched. Candidates such as Keith Jobson (Halifax Chebucto, 1967 – 503 votes), Burris Devanney (Halifax Chebucto, 1970 – 1180 votes; 1974 – 1648 votes), Muriel Duckworth (Halifax Cornwallis, 1974 – 2121 votes), and Mike Bradfield (Halifax Citadel, 1974 – 1452 votes, 1978 - 2015 votes) established the NDP as a viable alternative at the polls.

In 1981, Alexa McDonough was elected in Halifax Chebucto, defeating incumbent Walter Fitzgerald by nearly 500 votes, to become the first New Democrat elected to the Legislature (Legislative Assembly of Nova Scotia) for a mainland and Halifax constituency.  In 1983, she was elected Leader of the New Democratic Party of Nova Scotia becoming the first female party leader in Canada.  Alexa represented the constituency of Halifax Chebucto for twelve years.  Over this period, she had a caucus of from 1 to 3 people and she was the only woman in the Legislature.  Alexa worked hard in the legislature and also outside the legislature.  She worked to encourage more women to run for the NDP.  In the adjoining riding of Citadel, Eileen O’Connell took up the torch and won an increasing number of votes in the 1984 (2864), 1988 (3057), and 1993 (3800) elections.

With the Electoral Boundary review of 1992, the former Halifax Chebucto was split in two parts. The western portion (from the CN tracks to the top of Fairview) joined with pieces of what used to be parts of Halifax Bedford Basin and parts of Halifax Atlantic to create a totally new constituency, Halifax Fairview. The eastern portion of Chebucto, from the CN tracks to Windsor Street joined with the former Citadel south of Chebucto Road to become the Halifax Chebucto constituency as we know it today.

Alexa McDonough decided to step down from her leadership of the Nova Scotia NDP in 1993 and was soon persuaded to run for federal leader.  She took on that challenge with her usual grace and gusto and in 1995 won the leadership of the federal New Democrats.  She then brought the National Party from near oblivion back up to a respectable 21 seats in 1997.

In 1998, the provincial NDP, under the leadership of Robert Chisholm, was beginning to look like it could do very well in the upcoming provincial election.  The quality of the candidates was at an all time high.  Howard Epstein, a well-known lawyer and environmental leader, had been a city councillor for a number of years working to accomplish the introduction of such leading-edge programs as the curbside separation of compostibles.  In 1998, Howard was persuaded to leave his city council seat and to run for the NDP here in Chebucto.  Howard won the Chebucto seat in 1998 taking 45% of the vote.   The party took 19 seats, up from 3.  It was tied with the Liberals who fell from 40 to 19 and the Tories had 14 seats.  For the first time, the NDP formed the Official Opposition in Nova Scotia.

Since both federal and provincial legislative houses were in a minority situation, there then followed a string of elections. With the provincial NDP under the leadership of Darrell Dexter, Howard Epstein won the series of provincial elections in 1999, 2003, and 2006 with 54% of voters supporting him in 2006. On June 9, 2009 the NDP won a historic victory, forming the first NDP government in Nova Scotia's and Atlantic Canada's history, winning 31 out of 52 seats in the Legislature. Howard was elected for a fourth consecutive time in Halifax Chebucto, gathering 56.47% of the vote, the largest percentage for the NDP ever in Halifax Chebucto.

The NDP now has an all-time high of 32 sitting members, and forms the government of Nova Scotia. Halifax Chebucto has been extremely well represented over the past 29 years first by Alexa McDonough and now, Howard Epstein.