A prominent Winston & Strawn trial lawyer who has defended Fox News and Boeing Co. is working on an effort to possibly prevent Joe Biden and Donald Trump from winning the 2024 election.
Dan Webb, the 900-lawyer firm’s co-executive chairman, is aiding the centrist political group No Labels in an unusual effort to potentially run a third-party “unity” ticket featuring a Republican and Democrat—even as the group garners attacks from the left that it could tip a close election to Trump.
Americans “are entitled to another choice,” Webb, 78, said in an interview. “The idea they’re not allowed to do that because of some theory that we’re going to draw votes from one side—I don’t support that.”
The lifelong Republican is taking a visible role at a time when Big Law firms are increasingly squeamish about getting caught on the wrong side of hot-button political issues. “It is much more of a minefield than it was 10 or 20 years ago,” said Bruce MacEwen, a law firm consultant at Adam Smith Esq.
Several big firms have fled from associations with Trump. Perkins Coie, once a top firm for the Democratic Party, dialed back its political law work after top elections lawyer Marc Elias departed. Conservative lawyer Paul Clement left Kirkland & Ellis in 2022 after the firm, reportedly amid client pressure, asked him to drop a firearms client.
The work has become “more iffy” at corporate law firms, said Mark Braden, a BakerHostetler attorney and former Republican National Committee chief counsel. “There is so much anger out there, and it is so polarized, that defending certain political figures—people are afraid that it will piss off clients,” he said.
But there was Webb Jan. 19 on MSNBC’s “Morning Joe” pushing back on charges that No Labels would play Biden spoiler. A day earlier at the National Press Club in Washington, he announced that No Labels referred a complaint to the Justice Department over allegations that left-leaning and anti-Trump activist groups are trying to illegally sabotage the group’s efforts to get on the ballot in all 50 states.
“This is a big day for No Labels,” Webb, acting as a volunteer counsel, said in his opening remarks at the Press Club. “We’ve been taking it a long time and we decided it was time to fight back.”
‘Where He Likes To Be’
Webb’s career has often intersected with politics. President Ronald Reagan appointed him US attorney for Illinois’ Northern District, where he prosecuted infamous cases in the 1980s involving electoral and judicial corruption in Chicago.
He became close to former Illinois Gov. Jim Thompson, serving as a surrogate speaker for the Republican at various points during his tenure from 1977 to 1991.
Trump even at one point turned to Webb to be his counsel in special counsel Robert Mueller’s investigation into Russian interference in the 2016 election, however Webb turned it down to due business conflicts.
More recently, Fox News hired Webb and his law firm to lead its defense in a defamation case brought by Dominion Voting Systems over the network’s false claims relating to the 2020 election. That ended last April with Fox agreeing to a whopping $787 million payout.
“Where the action is, where the lights are shining brightly, that’s where he likes to be,” said Charles Kocoras, a senior judge in the Northern District of Illinois who worked with Webb early in their careers.
Webb identifies as a moderate Republican, which he called an extinct species in the modern GOP. During the 2016 election, Webb called Trump unfit to serve as president and urged Republicans in the private sector to follow him and vote for Hillary Clinton.
Republicans have to “get off our butts and financially support her and get out of the closet because there are enough of us to swing this election,” Webb told the Chicago Sun Times months before the election.
Webb, a prolific political donor, has continued to financially back Republican candidates, including donating $3,435 in October to former New Jersey Gov. Chris Christie’s failed bid for the GOP nomination.
No Labels Role
Now as a volunteer for No Labels, Webb remains unconcerned about taking on a role for a political group. He said Winston & Strawn, a Chicago-headquartered law firm, takes no position on politics and that there’s never been issues in the past over a person’s political activity.
To the contrary, he said, people in the private sector—just as he advised in 2016—need to get off their butts.
“I would like to see a unity ticket succeed,” Webb said. “That’s why I’m involved.”
The veteran lawyer said he learned about No Labels after the 2016 election and later met with people affiliated with the group in Chicago. He kept sporadic contact with them in the intervening years, including representing the group in a contract spat with a third-party vendor.
He decided to get more involved as a volunteer with the group about eight months ago because of polls showing the unpopularity of Biden and Trump.He said he’s participated in “strategy discussions” about the group’s goal of qualifying as a political party on the presidential ballot in all 50 states and has signed on to vet candidates for a possible nominating convention.
Still, Webb said he’s dedicating “very few hours” per week to the effort and that he views the work as part and parcel of a lifelong interest in politics. He is not billing the group for the work.
“Lawyers, maybe because of what they do, are interested in government and politics,” he said. “We’re not all just prisoners of working 18 hours a day in a law firm.”
Following the trip to Washington last month for No Labels, the lawyer was soon back in a Chicago courtroom, where his major clients include Boeing Co. in lawsuits tied to deadly crashes involving the aircraft manufacturer’s 737 Max.
No Labels’ ballot project has so far qualified for the presidential ballot in 15 states, the group said in a Feb. 2 announcement. Group leaders have said they will make a decision on whether a third-party candidacy has a legitimate shot at winning after Super Tuesday in March.
Webb is not involved in the on-the-ground ballot access work. A “robust team of other lawyers” is leading that effort, said No Labels chief strategist Ryan Clancy.
Clancy did not say who’s heading the program, however tax filings show an affiliated organization, Insurance Policy for America Inc., paid about $1 million to Capitol Advisors LLC, a Virginia-based consulting firm, for “ballot access” work in the first half of 2023.
No Labels, co-chaired by ex-Sen. Joe Lieberman (D-Ct.), also worked with the law firms Caplin & Drysdale and Osborn Maledon in its successful push to get on the ballot in the swing state of Arizona, court filings show.
‘Antithesis of Bridging Divide’
The work has fueled increasing attacks, with some politicians and advocacy groups branding No Labels a threat to democracy.
Progressive groups in January filed lawsuits alleging the group is a political committee and must disclose its donors. As a 501(c)(4), No Labels has argued it does not have to reveal its financial bakers, however if the group does offer a ballot line to a presidential ticket, those candidates would have to form committees subject to campaign finance rules.
Two members of the Durst real estate family also sued the group in January to recoup $145,000 they made in donations.
“No Labels played a ‘bait and switch’ here with major donors, claiming originally to be an organization committed to bipartisan unity and, instead, transforming today into a third party, which is the antithesis of bridging the political divide,” said Randy Mastro, a King & Spalding litigation partner representing the Dursts.
Webb claimed the Dursts’ suit was part of the “conspiracy” that No Labels referred to the DOJ. In that letter asking for an investigation, the group cited a Semafor report in which activists from groups such as the Lincoln Project discussed ways to tarnish the reputation of anyone associated with the group.
The group has claimed that anti-No Labels activity goes beyond protected speech and represents illegal harassment and intimidation. But such claims face a “very high bar” given the US’s broad political speech protections, said Braden, the BakerHostetler political law attorney.
“The last group that attempted to use the Justice Department to attack the Lincoln Project was the Trump administration,” Lincoln Project co-founders Rick Wilson and Reed Galen wrote in the Wall Street Journal. “It didn’t work then. It won’t work now.”