He attended the Roxbury Latin School for four years (being part of the Class of 1897), but was forced to withdraw before graduation because of family financial difficulties.

He was a good poultryman and considered himself a farmer for the remainder of his life, although in 1916 he moved to Manchester, New Hampshire, to resume a career as a bond salesman.

New Hampshire progressivism was characterized by an effort to democratize the processes and make equitable the administration of government and to challenge powerful economic interests such as the Boston and Maine Railroad.

Tobey's experience in the bonding business as well as his general reputation and political contacts led to his selection as New Hampshire Liberty Loan chairman during World War I.

Later, as a member of the New Hampshire Food Administration, he came to know Herbert Hoover, who, together with Bass and Charles Evans Hughes, greatly influenced Tobey's political beliefs.

In 1924 Tobey was elected to the New Hampshire Senate, and he served as president of that body during the administration of progressive governor John Gilbert Winant.

Bass and other internationalists among his old allies broke with Tobey on this issue, and the junior senator was further isolated when Styles Bridges became the champion of preparedness.

Facing an election challenge from the Bass wing of the party as well as from the followers of Bridges and Frank Knox, Tobey sought and received an appointment as delegate to the United Nations Monetary and Financial Conference at Bretton Woods, New Hampshire; he also defended the International Monetary Fund, but he still rejected the "one-worlders," as he described the Wendell Willkie wing of his party.

Tobey joined with Wayne Morse and George Aiken in opposing Robert A. Taft's leadership of the Senate Republicans and supporting President Harry S. Truman on several important votes during the 80th Congress.

A New York Times obituary noted that his "independence and sharp tongue made him one of the more colorful figures in American public life."