Orpen was well known for his many small acts of philanthropy and charity. He financed the operation of a soup kitchen for two years, although he shut it down after people complained that the soup was not good enough. Orpen opened his office on Fridays to whoever needed help. On one such occasion, when Canadian boxer
Sammy Luftspring could not afford to go to the 1935 Canadian Boxing Championship, Orpen gave him $50. On several occasions, Orpen refunded a gambler's losses when it became known that the gambler had gambled their rent or food money away. Orpen never recommended that people gamble; only that he would take their bets if they wished to bet. In 1890, sports writer
William Hewitt bet with Orpen at amounts he could not afford. Told that Hewitt made $9 a week, Orpen offered to let Hemitt bet privately with him for one month, betting on any horse in North America at 2–1 odds, one bet a day. After one month, Hewitt owed $18, or half his salary, which Orpen offered to forgive. Hewitt paid the debt and learned his lesson, "It was a cheap lesson and saved me thousands," wrote Hewitt. Although Orpen was involved in gambling when it was illegal, his gambling club and racetracks did not open on Sundays when opening on Sundays in Toronto was illegal. Orpen was also known for his lack of racial discrimination. Blacks and whites worked side by side at the Orpen tracks. Facilities were the same for both. On his 80th birthday, Orpen received congratulations from the
Mayor of Toronto, the
Premier of Ontario and the
Prime Minister of Canada. Orpen was quoted as saying "I will start to think I am a respectable citizen if this keeps up." ==Death==