Born in North Kensington to a British Jamaican family, Bailey earned a degree in computer-aided engineering from London South Bank University.

Amid the Partygate scandal, Bailey resigned from his position as chair of the London Assembly's police and crime committee after a photograph of him at a December 2021 gathering at the Conservative Campaign Headquarters emerged, attracting allegations that he had breached COVID-19 restrictions that were then in place in England.

[2] Bailey was the subject of an episode of the BBC Radio 4 series The House I Grew Up In, in which he admitted he had been a burglar in his youth and said: "I had a particular group of friends who indulged in a burglary.

[15] In May 2006, Bailey co-founded MyGeneration, a charity addressing the social problems that affect struggling young people and their families.

[16] In 2010, The Times reported that Bailey was at the centre of allegations that his North Kensington-based charity showed £16,000 worth of spending "without any supporting records".

[18][19] On 29 March 2007, Bailey was selected at an open primary to be the Conservative candidate for the newly recreated parliamentary seat of Hammersmith in West London.

[29][30] At the 2017 general election, Bailey contested Lewisham West and Penge, where he finished in second place with 12,249 votes.

The Telegraph published claims he was pushed out of Downing Street by David Cameron's "clique of Old Etonian aides".

[40] In October 2015, Bailey was selected as the third Conservative candidate on the London Assembly top-up list, after Kemi Badenoch and Andrew Boff.

[48] In 2018, Bailey was selected as the Conservative candidate for the forthcoming London mayoral election (scheduled to be held in 2020 but later postponed until 2021).

[50] Bailey was subject to racism during the campaign on social media and in a letter posted to a Conservative party office.

He shared a tweet with an image with a caption describing Sadiq Khan, the incumbent mayor of London, as the "mad mullah of Londonistan".

[52] In October 2018, Bailey was accused of Islamophobia and Hinduphobia over the contents of a pamphlet entitled No Man's Land, written for the Centre for Policy Studies in 2005.

In it, Bailey said that celebrating Muslim and Hindu festivals "[robs] Britain of its community" and risked turning the country into a "crime riddled cesspool" as a result.

[55] In June 2020, following poor polling figures against current-Mayor Sadiq Khan, the Financial Times reported that some senior Conservatives wished to replace Bailey with another candidate such as Sajid Javid.

[60] In early March 2021, Bailey was accused of politicising the disappearance of a 33-year-old woman in Clapham, given that the police investigation was still ongoing.

[67] Throughout 2020 and 2021, Bailey's mayoral campaign outlined several policies including:[69] In August 2020, he announced he would encourage larger businesses in London to drug-test employees in an effort to reduce drug consumption and crime.

[78][79] In September 2020, Bailey proposed that companies should be able to pay to rename tube lines and stations with commercial brand names.

[73] In January 2021, Bailey was criticised for suggesting in an interview with Inside Housing that homeless people would be able to save for this £5,000 deposit to purchase an affordable home.

[87] In 2006, Bailey said "by giving children condoms and the amount of sexual material they are exposed to you normalise sex and they feel it is their divine right to have it, when actually it is not", and added "that is one of the things that drives their self-esteem up or down and leads to crime".

[90] In an article in The Daily Telegraph in 2006, Bailey claimed that single mothers deliberately become pregnant in order to gain benefits, saying that they "won't be too careful about not becoming parents.

[101] On 14 December 2021, The Daily Mirror published a photograph of the gathering, revealing that property developer Nick Candy was also present.

[102] Following the release of the photograph, Bailey resigned from his position as chair of the London Assembly's police and crime committee.

[103] On 11 November 2022, the police decided to take no action against Bailey, and all others in attendance at the gathering, citing insufficient evidence[104] On 18 June 2023, the Mirror released previously unseen video recordings of the above event.

[110] Bailey has been accused of misogyny after he suggested on the GB News television channel that it was not possible for a woman to be a serious political commentator while at the same time posting flattering photographs on social media.

[111] The subject of his comments, Carol Vorderman, had been previously critical of Bailey's elevation to the House of Lords despite his involvement in the 'Partygate' scandal.