Now 59 years old, Calhoun largely retired from business. He invested in real estate, but all his efforts failed. He moved to New York City in 1914, where he lived off his wife's income and attempted to re-establish himself in business. In 1916, he was sued for failure to pay rent on his office, and the poor state of his financial affairs was exposed. He declared bankruptcy the same year. Although some sources claim he returned to Southern California in the 1930s and regained a portion of his fortune investing in oil fields, other sources say there's little evidence to suggest he made these investments or restored his fortune and that he died instead in obscurity.