D'Amato drew the nickname Senator Pothole for his delivery of "constituent services," helping citizens with their individual cases. Some New Yorkers meant the nickname as a pejorative.
Senator D'Amato also holds the record for the second and seventh longest filibusters ever recorded in the United States Senate. He is remembered for his unique and rather comical filibusters. In 1986, a filibuster he conducted against a military bill lasted 23 hours, 30 minutes and he was known for reading the District of Columbia phonebook during a filibuster. On another occasion he once filibustered a bill that would have caused the loss of 750 jobs in upstate New York by singing "South of the Border (Down Mexico Way)"
Senator D'Amato is also remembered for presenting a poster of a "Taxasaurus Rex," which he then stabbed with an oversized pencil.
He was a member of the President's Commission on Aviation Security and Terrorism (PCAST), which was set up in September 1989 to review and report on aviation security policy in light of the sabotage of Pan Am Flight 103 on December 21, 1988.
While he was in office, he was chair of the Senate Committee on Banking, Housing and Urban Affairs, and was a member of the Senate Finance Committee. As a member of the former, he became a leading critic of the Clinton administration regarding the Whitewater scandal, and during 1995 and 1996 chaired the hearings-heavy Senate Special Whitewater Committee. As a member of the latter, he championed the cause of Holocaust survivors trying to recover relatives' funds from accounts in Swiss banks.
D'Amato was known for being fairly conservative, a reflection of then conservative-leaning Nassau County, yet very popular among New York's liberal voters. He strongly supported the conservative positions of his party on "law and order" issues such as capital punishment and harsh penalties for drug offenses. On some issues he agreed with the opposition: in 1993 D'Amato was one of only three Republicans to vote in favor of allowing gays to serve openly in the U.S. military. In 1996 he was among the minority of Republicans to vote to extend federal protections against discrimination in hiring to homosexuals. In fact, in the 1998 election, D'Amato was endorsed by the Human Rights Campaign over socially liberal Democratic Congressman Chuck Schumer. On labor issues too he frequently sided with Democrats. His 1998 loss was attributed to a lack of support among moderate voters in New York City, site of opponent Charles Schumer's US Congressional district. Another factor contributing to his loss was his labeling of Rep. Schumer as a "putz-head," which means "fool" or "penis-head" in Yiddish. This was ironic on several levels: first, D'Amato had previously enjoyed considerable Jewish support because of his strong pro-Israel stance, as well as his efforts to help Holocaust survivors. Second, D'Amato won in 1992 for the same reason he lost in 1998; his 1992 opponent, then-attorney general Robert Abrams, called D'Amato a "fascist," which people (including D'Amato himself) interpreted as an ethnic slur because D'Amato is Italian. After his defeat, he became a correspondent for George Magazine until it ceased publication in 2001, and was also a commentator on Fox News. He is now managing director of Computer Associates and also serves as Chairman of the Board of the Poker Players Alliance.
D'Amato's decline may also have mirrored that of Nassau County's Republicans. In 2001, after years of alleged scandal and financial mismanagement, Republicans lost control of the county legislature for the first time in 40 years, and Democrat Thomas Suozzi was elected County Executive.
The senator's brother was also partners with Lucchese crime family captain Paul Vario and mob associate Phillip Basile. When Basile was arrested for getting mob associate Henry Hill a no-show job at one of his discos, Senator D'Amato testified on Basile's behalf.
During the Don Imus radio program on April 4, 1995, he used a mock Japanese accent to impersonate Lance Ito, a Japanese American judge overseeing the ongoing O.J. Simpson trial (Ito, born and raised in the United States, has a characteristically American accent). He later apologized on the Senate floor for his comments.
In 1994, he insulted Betsy McCaughey Ross, the Republican candidate for New York Lieutenant Governor; he joked that in order to get an endorsement for her running mate, George Pataki, she should have sex with New York City mayor Rudy Giuliani, who had endorsed Mario Cuomo.
In October 1998, D'Amato was criticized for insulting Congressman Jerry Nadler. According to USAToday, D'Amato "referred to the heavyset Nadler as 'Congressman Waddler.' He also did a physical imitation of Nadler (D-NY) waddling like a duck." D'Amato subsequently apologized, saying, "It was a poor attempt at humor, and I was wrong, and I apologized to him."