With a reputation as a racket-buster, Tompkins won a denaturalization order and indictment against mobster Albert Anastasia, who was found guilty and jailed on federal income tax evasion charges.
Bernard M. Shanley, a New Jerseyan who served as an Eisenhower's Deputy White House Chief of Staff, touted Tompkins as a potential Republican candidate for Governor of New Jersey against Robert B. Meyner in 1957.
The 1958 race for an open United States Senate seat in New Jersey created a long-term problem for Tompkins' political future.
He supported Shanley, who left the White House staff to become a candidate, against ten-term U.S. Rep. Robert W. Kean, who was from Tompkins' home county, Essex.
In the 1961 Republican gubernatorial primary, Kean backed Walter H. Jones, a State Senator from New Jersey, while Tompkins supported Eisenhower's U.S. Secretary of Labor, James P. Mitchell.
[9] In 1965, the U.S. Supreme Court, in Reynolds v. Sims (more commonly known as One Man, One Vote), required redistricting by state legislatures for congressional districts to keep represented populations equal, as well as requiring both houses of state legislatures to have districts drawn that contained roughly equal populations, and to perform redistricting when needed.