On the 40th anniversary of the historic Apollo 11 moon landing in 1969, the U.S. House of Representatives passed Grayson’s New Frontier Congressional Gold Medal Act of 2009. The bill asked the president to present Congress’s highest civilian honor, the Congressional Gold Medal, to Apollo 11 astronauts Neil Armstrong, Edwin “Buzz” Aldrin Jr., and Michael Collins, as well as John Glenn, the first American to orbit the Earth. Only about 200 medals have ever been awarded in the country’s history. The New Frontier Congressional Gold Medal Act of 2009 passed the House unanimously on July 20, 2009.

Grayson was the second Democrat to represent Florida’s 8th congressional district since its formation after the 1970 census (it was the 5th District from 1973 to 1993 and has been the 8th since 1993). The only other Democrat to represent this district, Bill Gunter, left to run for the United States Senate in 1974 after only one term.

Grayson was born in the Bronx, New York City, New York, to Dorothy Ann (née Sabin) and Daniel Franklin Grayson. He graduated from Bronx High School of Science in 1975, and also attended the Hampshire College Summer Studies in Mathematics program. Grayson worked his way through Harvard College as a janitor and nightwatchman, and also features reporter for Boston Phoenix. He graduated magna cum laude and Phi Beta Kappa with a Bachelor of Arts degree with a Special Concentration in Urban Studies in 1978. After working two years as an economist, he returned to Harvard for graduate studies. In 1983, he earned a J.D. cum laude from Harvard Law School and a M.P.P. from the John F. Kennedy School of Government. He also completed all coursework and the comprehensive examination for a Ph.D. in government.

Grayson worked as a law clerk at the Colorado Supreme Court in 1983, and at the D.C. Circuit Court of Appeals from 1984 to 1985, where he worked with two judges who later joined the U.S. Supreme Court: Ruth Bader Ginsburg and Antonin Scalia. He was an associate at the Washington, D.C. firm of Fried, Frank, Harris, Shriver & Jacobson for five years, where he specialized in contract law.

Grayson wrote his master’s thesis on gerontology. In 1986, he helped found the non-profit Alliance for Aging Research in Washington, D.C. and served as an officer of the organization for more than twenty years.

Grayson was married to a woman he met in the early 1980s at a party in Boulder, Colorado. Grayson remarried in 1990 to Lolita Grayson. The couple separated in March 2014, and Alan Grayson asked a court in Orlando to annul the marriage a year later. In April 2015 the Graysons agreed to settle the dispute and annul their 25-year marriage.

In 1991 he founded the law firm Grayson & Kubli, which concentrated on government contract law. He was a lecturer at the George Washington University government contracts program and a frequent speaker on the topic. In the 2000s, he worked as a plaintiffs’ attorney specializing in whistleblower fraud cases aimed at Iraq War contractors. One contractor, Custer Battles, employed individuals who were found guilty of making fraudulent statements and submitting fraudulent invoices on two contracts the company had with the Coalition Provisional Authority in Iraq. On behalf of his clients, Grayson filed suit under the False Claims Act and its qui tam provisions. The jury verdict was more than $13 million, which was upheld on appeal in April 2009. The Iraq War contractor fraud case brought Grayson his first national attention. In 2006, a reporter for The Wall Street Journal described Grayson as “waging a one-man war against contractor fraud in Iraq” and as a “fierce critic of the war in Iraq” whose car displayed bumper stickers such as “Bush lied, people died.”

In 2006, Grayson first entered into electoral politics, losing the 2006 Democratic primary for Florida’s 8th congressional district to Charlie Stuart, a prominent local businessman and conservative Democrat. Stuart went on to lose the general election to incumbent Republican Ric Keller.

In late 2007, Grayson announced that he would run again for the 8th district seat, and again faced Stuart in the primary. In the August 26, 2008 Democratic primary, Grayson defeated Stuart, 49%–28%, with three other candidates splitting the remaining 24%. During the general election campaign, Grayson maintained a consistent lead over Keller, who had only slightly won renomination in the Republican primary over attorney Todd Long. On election day, Grayson defeated Keller, 52%–48%.

Grayson is considered a progressive Democrat. He supported Barack Obama in 2008. He was a member of the Congressional Progressive Caucus, of which he was vice-chairman. Grayson twice joined Republicans to oppose the raising of the federal debt limit. He said, “We need to live within our means. We need to eliminate wasteful spending. If we did those two simple things, we would not need to raise the debt limit.”

On September 14, 2009, the U.S. House of Representatives passed H.RES 686, Grayson’s “Teach the Constitution Week” bill. The bill urged high schools to spend one week each September teaching the United States Constitution to high school seniors and also encouraged students to petition the government on an issue of personal importance to them to demonstrate their understanding of their rights and responsibilities as citizens of the United States. The non-partisan resolution was passed by a voice vote and featured 222 co-sponsors.

In September 2009, Grayson used a parliamentary maneuver called an “extension of remarks” to provide crucial instruction on H.R. 3221, the Student Aid and Fiscal Responsibility Act of 2009, a bill that, among other things, included a provision that prohibited funding for ACORN (the Association of Community Organizations for Reform Now). Grayson’s extension of remarks directed that the legislation defund any organization that cheats the federal government, not just ACORN. The defunding measure passed the House with a final vote of 253–171. Grayson also encouraged the public to report companies covered by the bill and set up a method to report offending companies via his Congressional website.

On September 29, 2009, in a late-night speech on the House floor, Grayson presented his impression of the Republicans’ health care plan, illustrated by signs. He said the Republicans’ plan was “don’t get sick”, and “if you do get sick, die quickly.” After demands from Republicans that he apologize, he defended his comment and in a House floor speech stated, “I apologize to the dead and their families that we haven’t voted sooner to end this holocaust in America.” He was then further lambasted for his use of the word holocaust by Jewish spokespersons across the nation. Grayson, who is Jewish, apologized to the Anti-defamation League for those offended by his generic use of holocaust. He also maintained that Congressional Republicans failed to offer a feasible plan. In October 2009, he launched NamesOfTheDead.com, a website to “memorialize Americans who die because they don’t have health insurance”. He subsequently read stories of the dead submitted through the Names of the Dead site on the House floor.

Grayson has tried to combat wasteful spending by government defense contractors by introducing his “Gold Plating” amendment. The amendment would require that cost or price account for half of the evaluation of bids for defense contracts. The law at the time allowed for cost to account for only 1% of the evaluation. The amendment passed as part of the National Defense Authorization Act in June 2009. However, the language was stripped from the final bill during the conference committee between Senate and House leaders. Grayson worked successfully to get the amendment inserted into H.R.5013, the IMPROVE Acquisition Act, which passed the U.S. House of Representatives on April 28, 2010.

In response to Republican arguments that the Obama administration’s preferred health care bill was too long and complicated, Grayson on March 9, 2010, introduced H.R. 4789, the Public Option Act (sometimes called the Medicare You Can Buy Into Act), a four-page bill that would allow all citizens and permanent residents of the United States to buy into the public Medicare program at cost. The bill attracted 82 co-sponsors and was referred to the Ways and Means Committee.

Grayson has been an outspoken critic of the wars in Iraq and Afghanistan. In May 2010, he introduced the War Is Making You Poor Act. The bill would require the president to fund the wars from the Department of Defense’s base budget. The bill does not necessitate an end to the wars or mandate a cut-off date. In addition to the tax cuts, the bill would cut the federal deficit by $15.9 billion.

Grayson was ranked as the 11th-wealthiest member of Congress in 2010, based on financial disclosure forms with a net worth of $31.41 million, and a pending claim against the now-defunct Derivium Capital for at least $25 million, according to Roll Call. Grayson disclosed that his attorney fees and costs for the war contractor case had exceeded $4 million.

On July 11, 2011, Grayson announced in an e-mail to supporters that he planned to run once again for Congress. Grayson ran unopposed in the Democratic primary for the newly created 9th District in Central Florida.

On November 6, 2012, Grayson defeated Todd Long, 63%–37%, to return to Congress after a one-term absence. He described his victory as “the biggest comeback in the history of the U.S. House of Representatives.” Although the two districts had different boundaries, Grayson claimed the House historian had told him that the shift from a 56%–38% loss in 2010 to a 63%–37% victory in 2012 was the biggest comeback in congressional history.

Known in his first term for making incendiary comments about Republicans, Grayson began to tone down his rhetoric and focused on working with Republicans to pass amendments that “appeal to the libertarian streak in the GOP”. He lobbied colleagues personally and in July 2013, David Weigel of Slate magazine called him “the most effective member of the House” and said that he was approaching “an unheralded title: The congressman who’s passed more amendments than any of his 434 peers.”

In October 2013, his campaign sent out a fundraising email that compared the Tea Party to the Ku Klux Klan. It used the image of a burning cross as the “T” in Tea Party. Matt Gorman of the National Republican Congressional Committee described the e-mail as “hateful words and imagery”. Grayson defended the comparison, saying that “here is overwhelming evidence that the Tea Party is the home of bigotry and discrimination in America today, just as the KKK was for an earlier generation.”

Grayson is pro-choice and supports increased funding for stem cell research. He has always supported same-sex marriage and said in an interviews in 2013, “the propaganda that somehow gay marriage makes straight marriage bad for everyone is just farcical to me. I just don’t understand the logic of it.”

On 31 May 2016, Alan Grayson married his third wife, Dr. Dena Minning. In 2016, Minning ran for the US House seat Grayson was vacating to pursue his Senate run. She was defeated in the Democratic primary.

In December 2019, Grayson released a book titled High Crimes: The Impeachment of Donald Trump.