Tenure
In November 1981, Grassley was one of 32 senators to sign a letter to President Reagan supporting Director of the Office of Management and Budget David Stockman. In August 1982, while the Reagan administration tried persuading senators to approve legislation authorizing the creation of a radio station for broadcasting to Cuba, Grassley joined fellow Iowa senator Roger Jepsen and Edward Zorinsky in seeking an amendment to the bill barring the Reagan administration from operating Radio Marti on that frequency or other commercial AM frequencies.
In October 1983, Grassley voted against establishing a legal holiday to commemorate Martin Luther King Jr.'s birthday. In 2015, an aide to Grassley said that he voted against the holiday due to an "economic decision both in the cost to the broader economy in lost productivity, and the cost to the taxpayers with the federal government closed". In 2004, Grassley co-sponsored legislation giving King a posthumous award, which became law on October 25 that year.
On November 1, 1984, Grassley signed a one-page citation of contempt of Congress against Attorney General William French Smith due to Smith's not turning over files on an investigation into Navy shipbuilding. Assistant Attorney General Stephen S. Trott called the citation "out of place" since Grassley was not acting at a session of the Judiciary panel he led.
In May 1987, the Senate Appropriations Committee defeated an attempt by Grassley to hasten payments of corn and other feed grain subsidies ahead of the scheduled payment taking place after October 1. Grassley's measure was also designed to unravel an accounting device lawmakers had used to make it appear that they were reducing spending for the incoming fiscal year.
In October 1987, during a press briefing, Grassley accused Reagan of being "asleep at the switch" and botching the handling of Robert Bork's Supreme Court nomination, adding that Bork's nomination had convinced him that the Reagan administration "has been terribly lucky for the last seven years" in other matters, including the economy and foreign policy. Later that month, Grassley likened the groups lobbying against Bork's nomination to the McCarthyism of the 1950s: "The big lie is standard operating procedure for some of these groups. All you have to do is repeat the same outrageous charges, and repeat them so often that people believe they are true." In November, as party leaders of the Senate Judiciary Committee met on the Supreme Court nomination of Douglas H. Ginsburg, Grassley released the text of a letter he intended to send to the American Bar Association suggesting the association was dragging its feet in reviewing Ginsburg's record. After Ginsburg admitted having smoked marijuana, Grassley said, "You like to think people who are appointed to the Supreme Court respect the law." Grassley joined Jesse Helms in resisting the nomination of Anthony Kennedy, Reagan's next choice for the Supreme Court; he indicated that he would have preferred that Reagan instead nominate Judge Pasco Bowman II or Judge John Clifford Wallace. Grassley expressed distaste for "the people who are committed to changing the judiciary" and taking "the path of least resistance".
In January 1989, as the Senate voted to schedule a vote within a month on a pay increase, Grassley asked how senators would decline federal program increases "come March and April if the first thing out of the box is a pay raise". In February, he was one of six senators to testify against the 50% pay increase scheduled to take effect the next week. In October, he was one of nine senators to vote against legislation intended to outlaw flag burning and other forms of flag defacement and joined Bob Dole and Orrin Hatch, the other two Republicans to vote against the bill, in voicing a preference for a constitutional amendment.
In January 1991, Grassley was one of only two Republican senators to vote against joining the international coalition to force Iraq out of Kuwait, the other being Mark Hatfield of Oregon. In August 1991, he became one of six Republicans on the Select Senate Committee on POW-MIA Affairs that would investigate the number of Americans still missing in the aftermath of the Vietnam War following renewed interest. In July 1998, President Bill Clinton listed Grassley among the members of Congress who had made it possible "for me to sign into law today the Internal Revenue Service Restructuring and Reform Act". On February 12, 1999, Grassley was one of 50 senators to vote to convict and remove Bill Clinton from office.
In May 2001, Grassley met with Democratic senator Max Baucus over the allocation of finances in tax cuts and both reported they were making progress in reaching a bipartisan deal, Grassley adding that the bill would contain all four of the main elements proposed by the Bush administration and the Senate Finance Committee would modify the components of the Bush proposal.
In August 2002, Grassley sent a letter to president and chief executive of the United Way of America Brian Gallagher requesting a detailed explanation on the overseeing of both finances and management of the organization's affiliates. Grassley also wrote to chief executive of the United Way of the National Capital Area Norman O. Taylor in regards to allegations of affiliates misappropriating money as well as withholding information the board needed to allow its conducting of oversight.
As a senior member of the Senate Finance Committee, Grassley has spearheaded many probes into alleged misuse and lack of accountability of federal money. In July 2007, a Grassley-commissioned report was released claiming that more than $1 billion in farm subsidies were sent to deceased individuals. Grassley was called a "Taxpayer Super Hero" in 2014 by the council for Citizens Against Government Waste. He received a 100 percent rating from the group that year and has a lifetime rating of 78 percent. Grassley was ranked the 5th most bipartisan senator of the 114th United States Congress and the 7th most bipartisan Senator in the first session of the 115th Congress by the Bipartisan Index, a metric created by the Lugar Center for the Lugar Center and Georgetown's McCourt School of Public Policy to rank members of the United States Congress by their degree of bipartisanship.
In February 2004, Grassley released an internal report composed by the FBI in 2000 that examined 107 instances of either serious or criminal misconduct by its agents over a 16-year period. In a letter to the FBI, Grassley called the report "a laundry list of horrors with examples of agents who committed rape, sexual crimes against children, other sexual deviance and misconduct, attempted murder of a spouse, and narcotics violations, among many others" and added that the report's findings raised questions about whether the FBI handled agents "soon enough and rigorously enough".
On June 28, 2006, Grassley proposed legislation intended to curb sex trafficking and sexual slavery by strictly enforcing tax laws, for example by requiring that a Form W-2 be filed for sex workers managed by a pimp or other employer.
Since 1976, Grassley has repeatedly introduced measures that increase the level of taxation on American citizens living abroad, including retroactive tax hikes. Grassley was eventually able to attach an amendment to a piece of legislation that went into effect in 2006, which increased taxes on Americans abroad by targeting housing and living incentives paid by foreign employers and held them accountable for federal taxes, even though they did not currently reside in the United States. Critics of the amendment felt that the move hurt Americans competing for jobs abroad by putting an unnecessary tax burden on foreign employers. Others felt that the move was only to offset the revenue deficit caused by domestic tax cuts of the Bush Administration.
In March 2009, amid a scandal that involved AIG executives receiving large salary bonuses from the taxpayer-funded bailout of AIG, Grassley suggested that those AIG employees receiving large bonuses should follow the so-called 'Japanese example', resign immediately or commit suicide. After some criticism, he dismissed the comments as rhetoric.
In May 2009, Grassley cosponsored a resolution to amend the US Constitution to prohibit flag burning.
When President Barack Obama and the Democratic Party proposed a health reform bill featuring mandated health insurance, Grassley opposed the health insurance mandate, saying that it was a deal breaker. In response to an audience question at an August 12, 2009, meeting in Iowa, about the end-of-life counseling provisions in the House health care bill, H.R. 3200, Grassley said people were right to fear that the government would "pull the plug on grandma". Grassley had previously supported covering end-of-life counseling, having voted for the Medicare Prescription Drug, Improvement, and Modernization Act of 2003, which stated: "The covered services are: evaluating the beneficiary's need for pain and symptom management, including the individual's need for hospice care; counseling the beneficiary with respect to end-of-life issues and care options, and advising the beneficiary regarding advanced care planning." In December 2009, he voted against the Patient Protection and Affordable Care Act (commonly called Obamacare or the Affordable Care Act). It was later reported that Grassley had notified Obama that he would vote against the Affordable Care Act even had the bill been modified to include all of the proposed modifications Grassley had proposed.
In January 2010, Grassley was one of seven Senate Republicans to sign a letter warning the White House about their serious reservations with Director of the Transportation Security Administration nominee Erroll Southers due to conflicting accounts Southers gave the Senate about his previous tapping of databases for information about his ex-wife's boyfriend in the late 1980s.
In December 2010, Grassley was one of 26 senators who voted against the ratification of New START, a nuclear arms reduction treaty between the United States and Russian Federation obliging both countries to have no more than 1,550 strategic warheads as well as 700 launchers deployed during the next seven years along with providing a continuation of on-site inspections that halted when START I expired the previous year. It was the first arms treaty with Russia in eight years.
In April 2013, Grassley opposed a gun control amendment authored by senators Joe Manchin and Pat Toomey, and instead proposed alternative legislation to increase prosecutions of gun violence and increase reporting of mental health data in background checks.
On March 9, 2015, Grassley was one of 47 senators to sign a letter to Iran led by Tom Cotton to rebuke the Joint Comprehensive Plan of Action. In June 2015, Grassley introduced legislation to help protect taxpayers from alleged abuses by the Internal Revenue Service. The legislation was proposed in response to recent events involving alleged inappropriate conduct by employees at the IRS but was opposed by Democrats.
Since first taking office in 1981, Grassley has held public meetings in all of Iowa's 99 counties each year, even after losing honorarium payments for them in 1994. This has led to the coinage of the term "full Grassley" to describe a presidential candidate visiting all 99 counties of Iowa before the Iowa caucuses.
In 2018, Grassley suggested that no women were serving on the Senate Judiciary Committee because of the heavy workload. The following week, Grassley added that he would "welcome more women" to serve on the Committee "because women as a whole are smarter than most male senators. And they work real hard, too".
In July 2018, after President Donald Trump nominated Brett Kavanaugh to the Supreme Court, Grassley lauded Kavanaugh as "one of the most qualified Supreme Court nominees to come before the Senate", and said that critics of Kavanaugh should lessen their confidence in how he would vote given past surprises in voting by members of the Court.
In 2016, Senate Republicans refused to consider Obama's nomination of Merrick Garland to the Supreme Court. At the time, Grassley said that the "American people shouldn't be denied a voice" in the nomination, which was "too important to get bogged down in politics". In 2020, after a Supreme Court vacancy arose due to Justice Ruth Bader Ginsburg's death, Grassley supported a prompt vote on Trump's nominee, backing the decision of "the current chairman of the Judiciary Committee and the Senate Majority Leader".
Grassley was participating in the certification of the 2021 United States Electoral College vote count when Trump supporters attacked the U.S. Capitol. He was removed from the Senate chamber and taken to a secure location when rioters entered the building. In the wake of the attack, Grassley said that Trump "displayed poor leadership in his words and actions, and he must take responsibility". He said efforts to impeach Trump would risk "further disunity" and that "the country must take steps to tone down political rhetoric and mend divisions". In response, The Gazette editorial board wrote that Grassley and other Iowa Republicans "must reckon with why they did the wrong thing for so long".
On January 3, 2023, Grassley became the Dean of the United States Senate.