[3] Healey's first attempt to enter Parliament was as candidate for Ryedale at the 1992 general election, where he finished in third with 13.8% of the vote behind the incumbent Conservative MP John Greenway and the Liberal Democrat Elizabeth Shields.

[7] Healey served as a member of the education and employment select committee from 1997 until he became the Parliamentary Private Secretary to the Chancellor of the Exchequer Gordon Brown in 1999.

[citation needed] In a Cabinet reshuffle on 5 June 2009, he was appointed Minister of State for Housing and Planning, replacing Margaret Beckett who had resigned.

While Minister of State for Housing and Planning, he was criticised for suggesting that more people renting properties rather than buying their own homes was a good thing.

[20][21] Following the election of Keir Starmer as leader of the Labour party, Healey was appointed Shadow Secretary of State for Defence in 2020.

[23][24][25] In May 2024, Healey visited Kyiv along with Shadow Secretary of State for Foreign, Commonwealth and Development Affairs David Lammy and met the head of the President's Office Andriy Yermak and Defence Minister Rustem Umerov.

In a joint statement, Healey and Lammy stated: "The next Labour government's commitment to Ukraine will be ironclad, and European security will be our first foreign and defence priority.

[31][32] In 2024, he said that the decision to go to war "wasn't sound at the time" and said the lesson was that military intervention could not have a successful outcome without sufficient diplomatic, economic, and security follow-through.

Healey said that he acknowledged that the European members of the alliance, have to take on more responsibility in guarding both Ukraine and the west against Russia and also the need to cooperate with the US regardless of who is inside the White House.

He noted that "these are serious times" with "rapidly increasing global threats" and said that he wanted to avoid "age-old tactics" by the armed forces over funds to back pet projects.

[41] Following a financial audit conducted by the government following the election, Healey warned of possible cuts on defence spending as "tough choices" lie ahead to tackle the £22 billion "black hole" in public finances.

Healey responded by saying that it was the government's "legal responsibility" to review export licences and to judge "whether there is a clear risk that anything we supply from this country could be linked to a serious violation of international humanitarian law".