[1] He was the eldest of two sons born to Arthur Chaskalson, who was a prominent anti-apartheid lawyer and who later served as Chief Justice of South Africa from 2001 to 2005.
[1][4] He was awarded silk in 2009, and as senior counsel he was a founding member of the Victoria Mxenge Group in 2011 and the Pan African Bar Association of South Africa in 2018.
[1] Judges Matter described the Mxenge Group as "a nascent project to effect racial, gender and diversity transformation in the advocates’ profession",[4] and the Pan African Bar Association was founded as an explicitly "black and women-oriented" organisation.
[9][1] His work at the State Capture Commission focused on illicit financial flows and he later assisted the National Prosecuting Authority's Asset Forfeiture Unit in related civil recovery efforts.
[1][4] A final major strand of litigation concerned freedom of expression (including in Islamic Unity Convention v Independent Broadcasting Authority, Khumalo v Holomisa, Phillips v DPP, and S v Mamabolo).
[1] In October 2023, President Cyril Ramaphosa announced that he would appoint Chaskalson as an acting judge of the Constitutional Court for two consecutive terms, first from 1 November to 15 December 2023 and then from 1 February to 31 March 2024.