Fingerhut received a bachelor of sciences degree from Northwestern University in 1981 and a law degree from Stanford University in 1984. He practiced law until becoming associate director of Cleveland Works, a post he served in from 1987-1989. Fingerhut served on the campaign staff and worked for Cleveland Mayor Michael R. White.

Fingerhut served as an Ohio state senator from 1991 to 1993. In 1992, he was elected to the U.S. House of Representatives and began serving in 1993 (103rd Congress). In his re-election bid in 1994, however, Fingerhut was defeated by Republican Steven C. LaTourette.

After his defeat in Congress, Fingerhut easily won a seat again in the Ohio State Senate. In 2004, he became the Democratic nominee to try to unseat incumbent U.S. Sen. George Voinovich, although his candidacy was overshadowed by speculation that TV show host Jerry Springer might enter the race. Fingerhut went on to lose to Voinovich on November 2, 2004, garnering less than 40 percent of the vote. During his Senate campaign, he chanted "I say Finger, you say Hut, Finger-hut! Finger-hut!"

In January of 2006, Fingerhut announced his candidacy for governor of Ohio joining U.S. Representative Ted Strickland who is also seeking the post.

On February 14, 2006 Fingerhut announced he would be dropping out of the race for governor, citing his inability to raise the funds and support needed to compete against Congressman Ted Strickland.