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Sirota continued to contribute to Capital & Main and interviewed Washington Governor Jay Inslee, a Democrat who launched a 2020 presidential campaign. They talked about how Inslee planned to address the issue of climate change through his campaign.

In May 2020, some weeks after ending his work with Bernie Sanders' 2020 campaign, Sirota joined Jacobin magazine as editor-at-large.

In March 2019, he began working as the senior advisor and speechwriter on the Bernie Sanders 2020 presidential campaign.

On March 19, 2019, the Bernie Sanders 2020 presidential campaign announced it had hired Sirota to work as a senior advisor and speechwriter. Sirota was accused of launching attacks against Sanders' Democratic opponents on Twitter and through articles for The Guardian on behalf of the campaign as early as December. However, according to Sirota and The Guardian, the Sanders campaign did not engage in conversations related to his hiring until January. The Guardian spokeswoman Deepal Patadia said after they were informed about the conversations Sirota quit filing columns for The Guardian.

On Twitter, Capital & Main stated on March 20, 2019,

The Atlantic wrote that David Sirota advised Bernie Sanders before leaving Capital & Main. Without commenting on the report's accuracy, Capital & Main didn’t know Sirota was advising Sanders. When we were told of his interest in working for Sanders, he stopped writing for us.

In 2018, Sirota argued immediate action must be taken against the influence and power of oil and gas corporations to fight climate change, and Democrats must choose a side. "Will our political class behold the fossil fuel industry’s sociopathy and realize that we face an existential choice between profits and ecological survival?" asked Sirota.

In January 2018, Sirota's wife, Emily, announced candidacy for a seat in the Colorado House of Representatives, promising a "bold, progressive agenda." In June, she won the Democratic primary in District 9, based in southwestern Denver. In November, she won the general election, with 72 percent of the vote to Republican Bob Lane's 28.

In March 2017, Sirota joined The Young Turks online broadcast network as a contributor, providing periodic investigative reports. In early 2018, after four years of reporting for the International Business Times as senior editor of investigations, Sirota left that publication.

In 2016, right-wing commentators at National Review and libertarian Reason upbraided Sirota for his 2013 Salon article titled "Hugo Chavez’s economic miracle". Sirota wrote in 2013 that Chavez was "no saint," but also that his socialist and redistributionist policies had led to Venezuela's GDP more than doubling and reduced poverty to the third-lowest level in South America. His detractors charge that Sirota overlooked that Venezuela's economic gains were based almost entirely on petroleum exports, and with the worldwide drop in oil prices Venezuela's economy has been in shambles, with shortages and rationing of food, electricity and toilet paper.

From 2009 to 2012, Sirota was the morning host at the Denver progressive talk station KKZN. Sirota was initially filling in for Jay Marvin on his eponymous program; but Marvin was ultimately unable to return, and Sirota became the permanent host in 2010. Sirota also guest hosted for Thom Hartmann and Norman Goldman. On July 16, 2012, Sirota moved to sister station KHOW to co-host an afternoon drive program with former George W. Bush administration FEMA director Michael D. Brown, The Rundown with Sirota and Brown. In January 2013, after nearly four years in radio, Sirota parted ways with KHOW/Clear Channel. Insiders speculate the reason for the abrupt departure was friction between the two co-hosts; it left Brown with his own show.

Sirota's book The Uprising was released in June 2008. It was ranked 20th on The New York Times bestseller list on June 15, 2008. The book was also listed on The New York Times Political Bestseller list for the month of July 2008. Sirota made speeches about his book at venues such as Hofstra University.

Sirota is a critic of neoliberal economic policies, and has leveled criticism at the Clinton, George W. Bush, and Obama administrations. Sirota supported John Edwards in the 2008 Democratic party primaries. He has criticized the Democratic Leadership Council and other Democrats, who he claims have "sold out" to corporate interests, and has argued that the term "centrist" is a misnomer in that these politicians are out of touch with public opinion. Sirota's article "The Democrats' Da Vinci Code" argues that leftist politicians are more successful in so-called "red states" than the mainstream media have previously reported. He is an opponent of free trade policies, a supporter of fair trade, and an advocate of workers' rights and organized labor. His May 2007 speech at the Montana AFL-CIO Convention in Butte articulated many of his views. Sirota supported Sherrod Brown over Paul Hackett for the 2006 Senate election in Ohio and criticized Hackett's claims that he was "forced out" of the race by party elders as disingenuous. In 2008, Sirota stated on radio program Democracy Now! that he had cast an early vote for Democratic Party presidential candidate Barack Obama.

Some other journalists and political analysts have criticized Sirota. In his article comparing two approaches to progressive politics, statistician Nate Silver disparaged Sirota's approach as "playing fast and loose with the truth and using some of the same demagogic precepts that the right wing does." Regarding Sirota's political analysis and projections, including his predictions during the 2008 presidential election, Al Giordano derided him as "an inverted compass: when Sirota says 'heads,' you can make a lot of money betting on 'tails.'"

Sirota was a contributor to OpenLeft, a now-defunct progressive political blog. In June 2007, he replaced the late progressive columnist Molly Ivins with a column to be syndicated nationally by Creators Syndicate. Sirota became a contributing writer for Salon in May 2011.

There was controversy in Washington, D.C., in 2007 about whether Sirota was a "journalist" or an "activist". While the Washington press corps tends to see him as an "activist", at one point he was criticized for skirting the rules about access to Congress, which would on some occasions deny activists access, by getting a "temporary intern's ID"; this gave him access to the Senate chamber, but he was criticized in The Washington Post afterwards. He was described as having "pulled an end-run around the press galleries." Sirota denied he got "special access" and that such a claim was "just bizarre." He added: "I think a lot of reporters on the Hill want to monopolize access to our government as a way to preserve their monopoly on news I guess." Some analysts observed that conservative journalists were activists as well; one noted "(Weekly Standard columnist) Fred Barnes has credentials, he espouses political views."

In May 2006, Random House's Crown Publishers released Sirota's book Hostile Takeover. The first chapter of the book was published in The New York Times in July 2006. Sirota read sections of his book in public. In the book, Sirota argued that corporate interests are driving U.S. economic policy. The book became a The New York Times bestseller on July 9, 2006, entering at #23 on the nonfiction list. The paperback edition came out a year later.

Sirota's Hostile Takeover (2006) was reviewed by The New York Times critic Tobin Harshaw who described Sirota as a "Montana-based blogger with a take-no-prisoners mind-set" with "an admirably organized mind". Harshaw applauded some Sirota suggestions as "admirably specific, occasionally realistic and arguably on the side of the angels" and capable of bipartisan support, such as his recommendations for "regulating malpractice insurance for doctors ... restoring state control over class-action laws ... (and) forcing chief executives to certify corporate tax returns so they face liability for fraud." He felt Sirota was critical of "mainstream Democratic centrists". Harshaw criticized the writing style as "cliched" and "oppressive" and too lengthy and needing an editor, but admitted Sirota presented a "creditable analysis."

In May 2005, Sirota became a contributor to The Huffington Post while writing his own blog. He was a regular guest on The Al Franken Show and makes guest appearances on The Colbert Report, Countdown with Keith Olbermann, NOW, Lou Dobbs Tonight, CNBC, and NPR. He is a senior editor at In These Times, a regular columnist for The Nation and the Intermountain Jewish News, and a past contributor to The American Prospect. He has been published in The Washington Post, the Los Angeles Times, the Baltimore Sun, and the San Francisco Chronicle.

In 2003 Newsweek profiled Sirota as a "political operative" skilled at "hacking out a daily barrage of anti-Bush media clips, commentary, and snappy quotes" who made "guerrilla attacks on the Bush administration" and who was "well schooled in the art of Washington warfare." According to the article, Sirota's main weapons were computer emails. Sirota was described as the "Internet child of the Clinton War Room generation." Former Clinton White House chief of staff John Podesta said of Sirota: "I just saw he had an eye for critique and the instinct for the jugular." For example, Sirota unearthed a two-year-old comment which Colin Powell had made to the effect that "Iraq posed no threat to its neighbors, and possessed no 'significant capability' in weapons of mass destruction." Sirota made Powell's statements more widely known. Reporters pounced, and it became a public relations blow to the Bush administration. Sirota was credited with having revealed that $87 billion for Iraq could have been used to erase huge state deficits at home, a fact that was repeated by Democrats nationwide.

He served as a senior strategist for Brian Schweitzer's unsuccessful 2000 Senate campaign and successful 2004 gubernatorial campaign. In September 2006, Sirota worked as a political consultant for Ned Lamont's U.S. Senate campaign. Lamont defeated Joe Lieberman in the primary, but Lieberman ran as an independent and defeated Lamont in the November election. In 2008, Sirota was co-chair of the Progressive Legislative Action Network (now renamed the Progressive States Network). He was a senior fellow at the Campaign for America's Future.

Sirota's career in political campaigns began when he became a research director for Illinois State Senator Howard W. Carroll's unsuccessful run for U.S. Representative in Illinois's 9th congressional district in the 1998 election; Carroll lost in the Democratic primary to J. B. Pritzker and Illinois State Representative Jan Schakowsky. In 1999, Sirota served as Dwight Evans' deputy mayoral campaign manager in Philadelphia but was let go for "overzealous behavior" related to the creation of a fake website with damaging racial comments attributed to their opponent John White, Jr. Evans said he believed that Sirota had not created the bogus page but had discussed it with the person that created it. Sirota then became a fundraiser for Joe Hoeffel in his first successful campaign for the House of Representatives in Pennsylvania's 13th congressional district. Later he moved to Washington, D.C. and worked in the political department of the American Israel Public Affairs Committee (AIPAC). His next job was as press aide and spokesperson for Bernie Sanders while he was serving as the at-large U.S. Representative from Vermont.

David J. Sirota (born November 2, 1975) is an American political commentator and radio host based in Denver. He is a nationally syndicated newspaper columnist, political spokesperson, and blogger.