Trump has already deployed Homeland Security agents to Portland on the grounds of protecting federal buildings from protesters, drawing intense criticism from local leaders who say the federal presence has only exacerbated tensions rather than promoting public safety.
On July 2, U.S. District Judge Michael H. Simon ruled that journalists with professional or authorized press passes and legal observers are exempt from Portland police orders requiring protesters to leave during declared unlawful assemblies or riots.
The mayors of New York City and Chicago said on Tuesday they would take President Donald Trump to court if he sent unidentified US government agents to police their cities, pushing back on a threat that has sparked widespread controversy over the use of federal force.
"There's no place for Trump's secret police in our city", Keller said. It was unclear whether officers had been deployed to other cities.
While the protests have largely been peaceful, Trump and his allies in conservative media have portrayed the cities as out of control as he tries to contrast himself with Biden and make the case to voters - especially the suburban women who turned against Republicans in the 2018 midterms - that failing to elect him for a second term will lead to lawlessness.
It was unclear where else the federal agents would be deployed, but the Associated Press suggested the president would target "other Democratic-run cities" in an effort to "supplement local law enforcement in ways that bolster his reelection chances".
What's going on in Portland?
They're the kind of scenes you'd expect to see in a dystopian movie: unidentifiable military guards grabbing protesters from the streets and putting them into unmarked vehicles; a photojournalist getting shot 10 times with impact munition by federal agents; angry demonstrators storming a police union building and setting it on fire.
Lightfoot sent the letter Monday afternoon, after telling reporters at an unrelated morning news conference that she was anxious about the president's plans, even as he told reporters at the White House the officers could help bring order to Chicago.
What happened after federal forces arrived?
"I've been documenting violent and militarized police responses to protests in Portland for more than four years, but nothing prepared me for the unrestrained brutality I've witnessed and experienced in recent days", the ACLU's Doug Brown said this week. Demonstrators broke windows and did other damage, hurled stones at the officers and shined lasers in their eyes. Despite their peaceful actions, "federal officers used tear gas and flash bangs to disperse the crowd", Buzzfeed reports.
Mr Wolf also denied claims that the security officers had no identification and insisted they were wearing insignia showing they were police.
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"These police officers are not storm troopers, they are not Gestapo".
"These agents won't be patrolling the streets", U.S. Attorney Timothy Garrison said.
Federal lawyers argue that isolating and identifying each press representative through a press pass or legal observer through a particular colored-hat or vest would be too hard in the course of a dispersal action.
To a certain extent, it is legal.
Acting DHS Secretary Chad Wolf appeared on a Fox News segment on Tuesday night, discussing the ongoing protests and rioting across Portland, which he says have continued for "52 nights in a row" as federal officers there are stretched to the limit.
The response follows a motion filed by 10 journalists and observers with the American Civil Liberties Union of OR seeking a temporary restraining order to hold federal officers to the same restrictions that a judge recently placed on Portland police.
Portland officials said they did not know about the federal action. The judge noted that past legal decisions have required a state to establish a very high bar - "quasi-sovereign interest" - in order to successfully sue the USA government. "And for a security or law enforcement organization, the loss of public trust can be fatal".
Another law, the Insurrection Act, lets presidents deploy US forces to suppress domestic insurrection.
The move is President Trump's latest effort to use an agency - created after the September 11 attacks to protect the country from terrorists threats - to supplement local law enforcement in ways that have alarmed critics.
President Trump's administration also faces multiple lawsuits questioning its authority to use broad policing powers in cities.
"The president is not the king", said Kent Greenfield, a Boston College law professor specializing in constitutional law.