His father was a member of the New South Wales Legislative Assembly from 1887 to 1891 and his mother was the daughter of William Lawson, one of the three explorers who made the first settler crossing of the Blue Mountains in 1813.

He was also deputy president of the now abolished Court of Arbitration, which dealt with industrial disputes between employer and employee, as well as setting minimum wage standards in the state.

Street also sat in the now abolished Vice-Admiralty Court, first established in New South Wales during the time of Governor Arthur Phillip to deal with maritime disputes.

His career confirmed that public confidence in the integrity of our judiciary which is so strong a foundation for a stable and civilized society [...] His temperament was splendidly judicial, remarkably free from any possible bias of opinion or emotion, apt to see any issue in board perspective, and quick to penetrate to its essentials.

These qualifications, combined with wide experience of various jurisdictions, especially that of Equity, made particularly acceptable his succession to Sir William Cullen as Chief Justice."

The most significant of these were concerning the administration of the Returned Soldiers' Settlement Branch of the Department of Lands in 1921 and the case against the Industrial Workers of the World (IWW) in 1918.

He had a wide knowledge of law and the ability to quickly reach the heart of the matter; however complicated a case might seem on the surface, the real issue involved soon became apparent to him.

Though he had a keen sense of humour his court never lost its dignity and decorum, and though he would not allow himself to be fettered by mere technicalities, he insisted on the maintenance of the basic principles of law.

He was in 1934 appointed American non-national member of the international commission provided for by the treaty between the United States of America and Greece.