Seattle-based Perkins Coie isn't typically the underdog in a court fight.

For more than a century, the Seattle law firm has zealously defended the biggest names in Seattle business, from Boeing to Microsoft to Amazon. It has grown from a hometown stalwart to a global player, with $1 billion-plus in annual revenues and 1,100 attorneys in 21 offices in the U.S., Asia and Europe.

But Perkins hasn't faced an opponent like Donald Trump, who seems determined to punish the firm for its work for the Democratic Party.

On March 6, Trump signed an executive order effectively barring Perkins from handling federal cases or representing federal contractors.

It's payback for what the White House called Perkins' "dishonest and dangerous activity," including controversial opposition research about Trump that Perkins arranged on behalf of the 2016 Clinton campaign.

On Tuesday, Perkins filed a suit claiming the order violated the Constitution, and on Wednesday, a federal judge temporarily blocked parts of the order.

Still, Trump's "retaliatory animus," as U.S. District Judge Beryl Howell called it, has already frightened off some Perkins clients and could financially cripple the 113-year-old firm, according to lawyers representing Perkins.

Trump's animus could also make other law firms rethink their own work for political clients — all the more since Trump is going after Perkins years after most of its political law team has left.

"It's obvious that they're doing this just to send a message to law firms that if they do something that is counter to Trump's interests, they're going to get punished — forever," said Hugh Spitzer, an expert in constitutional law and legal ethics at the University of Washington School of Law.

For Perkins, the wrath of Trump is the latest challenge to what was until recently one of the nation's dominant political law practices.

From the 1990s to 2021, Perkins became the go-to law firm for Democrats in election disputes, including some of the most consequential contests in recent history.

Washingtonians will recall Perkins leading Democrat Chris Gregoire's successful recount effort against Republican Dino Rossi in the 2004 governor's race.

But Perkins also became a force in national politics. The firm represented the Democratic National Committee and the Democratic House and Senate fundraising operations, advised Democratic presidential campaigns, and shaped party strategy in election fights, voting rights battles, redistricting and related matters.

Along the way, Perkins' political team became a kind of who's who in Democratic politics.

Bob Bauer, who founded Perkins' political law practice in the early 1980s, went on to serve as President Barack Obama's White House counsel in 2009 and President Biden's personal attorney.

Marc Elias, Bauer's successor at Perkins, led numerous Democratic election fights, including the litigation barrage that defeated Trump's effort to overturn the 2020 election.

For much of the last three decades, "they were hitting above their weight for a Seattle firm," said Douglas Ross, a former U.S. Justice Department attorney who teaches at the University of Washington law school, of Perkins' political successes.

That success partly reflects a broader surge in election-related litigation that followed the contested presidential election of 2000.

That battle, which was ultimately decided by the U.S. Supreme Court in Bush v. Gore, "taught political operatives .... that when contests are close enough to be within the margin of litigation, it makes sense to fight on rather than to concede," according to a Harvard Law School report. Legal spending by both parties ballooned.

But Perkins' success also reflected the talents and agendas of the attorneys leading its political law practice, which eventually grew to around 50 lawyers.

Exhibit A was Elias, a brilliant, combative New York native who joined Perkins out of law school in the early 1990s and became known for both legal acumen and media savvy, according to legal experts and press accounts.

A turning point for Elias and Perkins came with the firm's work on the high-profile 2008-09 recount battle by Minnesota Democrat Al Franken over a Republican Senate incumbent.

As The New York Times later put it, that battle "led to time in front of news cameras and millions of dollars in legal fees, helping to usher in a new era in which political law, once regarded in legal circles as an unprofitable backwater, came to be seen as an appealing growth market."

Between 2009 and 2021, Perkins billed around $150 million to various Democratic organizations, according to The American Lawyer, a trade journal.

Even at its peak, Perkins' political law practice was just a small fraction of the firm's overall business, according to court filings.

But "because it's such a visible practice, and because it is the leading [political law] practice in the country, it brings us a lot of attention and is part of our brand, particularly in Washington D.C.," John Devaney, Perkins' then-managing partner, told Forbes in 2017.

But legal experts say an aggressive, influential political law practice can come with costs.

Perkins was heavily criticized over the so-called Steele Dossier.

In 2016, Perkins used funds from the Clinton campaign and the Democratic National Committee, without their knowledge, to pay for opposition research by former British spy Christopher Steele purporting to show that the Russian government helped the Trump campaign, according to media reports and to 2017 court filings by Perkins.

Although Russia's interference in the election has been substantiated by the U.S. Justice Department and others, many of the claims in the Steele Dossier were later largely debunked.

Elias has also come under fire for helping pass 2014 legislation that raised the amount of money national political parties could receive from wealthy donors.

Even Perkins' outright political law successes have proved costly.

Tension within Perkins over publicity from the Steele Dossier debacle and other political law work was one of the reasons Elias left Perkins in 2021, along with around 50 of the firm's attorneys, to start his own political law practice, according to media accounts and court filings.

Perkins declined to comment on Elias' departure, and Elias did not respond to an interview request.

But it's notable Perkins hasn't rebuilt its political law practice to anything approaching its pre-2021 scale.

Today, the practice has a handful of attorneys and focuses in large part on compliance with political and electoral regulations. It generates around a half a percent of the firm's annual revenue, down from around 4.5% prior to 2021, according to media accounts and court filings.

In a 2022 interview with Bloomberg, Perkins managing partner Bill Malley said Perkins was looking to expand its other practice areas, including in the tech sector, but expected to pull back from politics: "We continue to have some work in that area, but it is much less than in the past."

Ironically, Elias departure and Perkins' much-diminished role in Democratic politics hasn't been enough to avoid retaliation by Trump.

Warning signs were apparent last fall. "WHEN I WIN, those people that CHEATED will be prosecuted to the fullest extent of the Law," Trump posted on his social media platform, Truth Social, in October. "Please beware that this legal exposure extends to Lawyers ..."

Trump's March 6 executive order spells out a long list of grievances with Perkins that go beyond the Steele Dossier.

It accuses Perkins of working with "activist donors ... to judicially overturn popular, necessary, and democratically enacted election laws, including those requiring voter identification."

It also alleges that Perkins "racially discriminates against its own attorneys and staff, and against applicants," and uses hiring "quotas" based on race and other discriminatory factors."

The order imposes harsh penalties by, among other things, suspending Perkins' federal security clearances and requiring other federal contractors to disclose any relationship with the firm.

In its lawsuit, Perkins disputes the accusations. It claims the executive order seeks to deprive the firm of business and privileges without due process, in violation of Perkins' constitutional guarantees of free speech and due process.

Given that many of Perkins' clients are federal contractors or have matters in federal courts, Trump's order "could spell the end of the firm," said Dane Butswinkas of Williams & Connolly, a high-powered Washington, D.C., firm representing Perkins.

In granting a temporary restraining order Wednesday, Judge Howell characterized Trump's executive order as an attempt by the administration to "intimidate" not just Perkins but any law firm.

It "casts a chilling harm ... across the entire legal profession," Howell said.

Trump has also faced criticism for an executive order last month targeting Covington and Burling, which represents former special counsel and Trump nemesis Jack Smith.

Howell's concerns have been echoed by numerous legal and professional organizations, including the Washington state attorney general, as well as more conservative organizations such as the Cato Institute.

"In many other countries that have lost their freedom, the rulers have made it an early order of business to intimidate if not do away with the sectors of the bar that were willing to represent opposition and dissident clients and challenge government actions," wrote Cato's Walter Olson last week. "It is alarming to see the United States moving rapidly down this path."

Indeed, late Friday Trump reportedly signed an executive order attacking New York firm Paul, Weiss. One of its former attorneys — Mark Pomerantz — investigated Trump while working for the district attorney's office in Manhattan, according to The New York Times.

Where the Perkins-Trump dispute is headed isn't clear. Trump could lose in court, but still claim a victory of sorts: Perkins is no longer the Democratic legal machine it was a few years ago.

Yet by all indications, Perkins Coie will continue irritating the president.

On Feb. 6, Perkins Coie attorneys working pro bono with advocacy groups filed a federal lawsuit challenging a Trump executive order, this one targeting transgender members of the U.S. military.

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