When the Crash occurred in 1929, the Toronto Daily Star labeled Cutten, "The Samson who pulled down the pillars of the Exchange," in New York. Cutten went to great lengths to dispel this story, even phoning the offices of the Guelph Daily Mercury to insist that he had suffered significantly himself. Many didn't buy his story, including the New York newspapers. In the 1930 book Mystery Men of Wall Street, New York newspaperman Earl Sparling contends that Cutten survived the Crash with a fortune of as much as $80,000,000, "Without unloading his basic holdings during the decline and fall of the market." Finally, on April 11, 1934, the Federal Government charged Cutten with failing to report $50,000,000 in grain futures holdings in 1930 and 1931. He was also charged with tax evasion in various years dating back to 1929, putting him in select company with gangster Al Capone as the only other resident of Chicago to find himself in this trouble. Under American law, when a broker or individual held 500,000 bushels or more in any one wheat option, or was 'short' that much, a report had to be made to the government. The government produced evidence that Cutten had accounts in the names of his wife, numerous friends, and relatives and some designated merely by numbers. The charge was that he juggled his holdings to keep each account below 500,000 bushels, but in 1930, he had at times been short as much as 2,000,000 and in 1931, 6,000,000. As a result, Cutten was banned from grain trading, a ruling later reversed by the Federal Circuit Court of Appeals at Chicago due to a technicality in the wording of the law and upheld by the Supreme Court of the United States.

As these legal problems mounted for Cutten, his health began to deteriorate. Already suffering from a chronic heart condition, he was stricken with double pneumonia in November of 1935, and was confined to bed from this point on. On March 11, 1936, deputy marshals went to his bed-side and served him with a warrant based on a federal indictment charging him with evading $414,525 in taxes in 1929. Cutten signed a $35,000 surety bond guaranteeing his appearance in court when the case was brought to trial. On June 6, 1936, Cutten officially resigned from the markets, citing poor health as the reason. It was also apparently the first time he was able to get up from bed and walk around a little since his illness began. Arthur W. Cutten died of a heart attack in his sleep at the age of 66, on June 24, 1936. Funeral services were held at St. Luke's Episcopal Church in Chicago. His body was then returned to Guelph a day later to be buried at the Woodlawn Cemetery. Today a 36-foot-tall obelisk, the focal point of the cemetery, marks his gravesite.

While the U.S. Federal Government dropped all criminal charges against Cutten at his death, they continued to pursue his unsettled tax account. What began as a $414,525 penalty quickly grew in the months following his funeral, escalating to $1,132,000 by the end of 1936. However, when the government pursued the unsettled account with his estate, they learned that Cutten's total wealth amounted to a paltry $350,000. Not believing this, the government decided to launch a thorough investigation. Thus began an unsettled investigation that is still the cause for rumour and debate today. According to Weekend Magazine, "Shortly before his death... Cutten is said to have transferred his assets, a reported $90,000,000, to Canada. Others contend he went broke like everyone else. The preference for one ending over the other is largely a question of temperament." As a part of their investigation, Federal U.S. agents paid a visit to the Cutten Club, but nothing was found. Of interest is the fact that Cutten Club architect and one-time owner, Stanley Thompson, often added fuel to the debate. In his book The Toronto Terror (a reference to Thompson), James A. Barclay reported that, "Stanley Thompson helped feed the rumour that Arthur Cutten had millions of dollars, illegally earned, stashed away in a wall of the clubhouse. But he (Thompson) never came across a cent."