[4] In 1897, Millar purchased the BC Express Company from Stephen Tingley and took over the government mail delivery contracts for the Cariboo region in British Columbia.

However, the railway was already planning to purchase the property and they convinced the Department of Indian Affairs to cancel their negotiations with Millar.

Millar died in his law office in the Crown Life Building at Yonge and Colborne Streets on October 31, 1926, of a stroke.

His funeral was held at his home on 75 Scarborough Road in the Beaches district of Toronto, attended by many other members of the legal profession.

The Royal Customs Commission held an inquiry in March 1937 and evidence was given that Millar had sent for the books to be delivered to his office.

[17] Though highly successful in the law and in his investments, Millar was known for his love of jokes and pranks which played on people's greed.

One favourite was to leave money on a sidewalk and watch from a hiding place as passers-by furtively pocketed it.

[citation needed] As a law student, Millar was jilted once by a girl of a prominent family and never had a serious relationship again.

Millar's final prank was his will, which says in part: This Will is necessarily uncommon and capricious because I have no dependents or near relations and no duty rests upon me to leave any property at my death and what I do leave is proof of my folly in gathering and retaining more than I required in my lifetime.The will had several unusual bequests:[19] The home in Kingston, Jamaica, had already been sold by Millar.

The 99 ministers and the 103 Orange Lodges who accepted the bequest, did so upon the sale of O'Keefe in 1928 for $1.35 million, in an agreement with the executors.

It required that the balance of Millar's estate was to be converted to cash ten years after his death and given to the Toronto woman who gave birth to the most children in that time.

[2] The will survived ten years of litigation, including attempts by Millar's distant relatives to have it declared invalid, and the Derby continued uninterrupted.

[29][30] It was speculated that Millar prepared this clause in his will to outrage the moral sense of Canadians and lead to reforms such as ending prohibitions against birth control.