Just as the water was settling in the Rocky River basin, the Stock Market crash of 1929 heralded in significant political changes. Even before Roosevelt's election in 1932, Roraback's "boss" status can be seen to have come under negative scrutiny as is evidenced in Lane W. Lancaster's "The Background of a State 'Boss' System" (American Journal of Sociology, Vol. 35, No. 5; Mar., 1930, pp. 783-798).
The "Boss" himself hails from a tiny hamlet in the most Yankee portion of the state, Litchfield County; he understands the language and the point of view of his neighbors and wins their steady allegiance...[reforms would] render precarious the position of the present system.
Roraback, who was close to Herbert Hoover (they had lunch two weeks before the crash), saw a loss of influence as the Great Depression progressed, but he remained a powerful influence in the Republican party until his death.
Through the 1920s and 30s, Roraback spent much of his time in Hartford, but he maintained his rural persona and status with a home in Harwinton in the heart of Litchfield County Connecticut. The Skinner House where he lived still stands, though, in a different location.
Roraback reportedly suffered from some serious health issues coincident with the changing economic fortunes of the country. Roraback's exercises in power also appear to have had been mostly out of the public eye in the 1920s. However, more attention was paid to his role in Connecticut politics and Republican party business after 1932. Roraback's health issues, whatever they were, could not have been helped by the greater attention his dealings had started to receive.
Additionally, as Candlewood Lake was filling with water pumped from the Housatonic, a John Anthony Craig was born to Mary Collins, Roraback's personal assistant, in New York City in August of 1928. According to Craig's obituary, J. Henry Roraback was Craig's father.
Mary Collins was described in Edwin Dahill's dissertation as a: "small, rather plain and efficient lady who devoted her entire working career to Roraback, handled his personal affairs and was consulted and thoroughly relied upon by him." In addition to the obituary, Craig, who had been an attorney, was linked to Roraback in the 1990s when he donated Roraback's papers to the Connecticut State Library where they are now stored.
In May of 1937, Roraback and his son Lewis went on a morning hunt at their Harwinton, CT home. Later in the day while preparing for him and his son to drive to meet Roraback's wife in Hartford, Roraback, in the yard of his house, shot a revolver into his temple. Some accounts describe the event as being witnessed by Roraback's butler with Lewis in earshot. Roraback's health was widely claimed to have been the impetus behind the suicide.
There is no record of any serious inquiry regarding Roraback's suicide.