The federal prosecutor’s office in Manhattan accidentally filed an internal memo that poked holes in the Trump administration's strategy to kill New York's toll on driving in Manhattan — arguing the government should change tactics if it wants to block the nascent program.
The memo, intended for a U.S. Department of Transportation attorney, was inadvertently filed Wednesday night in New York's lawsuit against the administration over its efforts to shut down the fee.
The blunder came days after the Trump administration gave New York a third ultimatum to stop collecting the toll, which started in January and charges most drivers $9 to enter the most traffic-snarled part of the borough.
In the memo, three assistant U.S. attorneys from the Southern District of New York wrote that there is “considerable litigation risk” in defending Transportation Secretary Sean Duffy's decision to pull federal approval for the toll and that doing so would likely result in a legal loss.
Instead, the three attorneys wrote, the department might have better odds if it tried to end the toll through a different bureaucratic mechanism that would argue it no longer aligns with the federal government's agenda.
Nicholas Biase, a spokesperson for the Southern District of New York, said in a statement Thursday that the filing was “a completely honest error and was not intentional in any way."
The Transportation Department, meanwhile, took aim at the Manhattan federal prosecutor’s office and said it was pulling the Southern District off the case.
"Are SDNY lawyers on this case incompetent or was this their attempt to RESIST? At the very least, it’s legal malpractice," a spokesperson for the agency said.
The statement comes after several top prosecutors in the office resigned and defiantly criticized their bosses in Washington, saying they were asked to handle a now-dismissed corruption case against Mayor Eric Adams in a manner they concluded was unethical, improper and wrong.
Jay Clayton, President Donald Trump's nominee to lead the office, was sworn in this week.
Trump, whose namesake Trump Tower is within the “congestion pricing” tolling zone, has been a vocal critic of the program and had promised to kill it once he took office.
His administration in February ordered the state to shutter the program, saying it was revoking federal approval for the toll. Duffy has described the program as “a slap in the face to working class Americans and small business owners."
Within minutes, New York filed suit in federal court to keep the program alive and said it would continue to collect the toll until ordered to stop by a judge.
The Transportation Department repeatedly has urged New York to shut down the toll and has threatened to pull funding and approvals from various transportation projects if it fails to comply.
The toll amount varies on the kind of vehicle and time of day. It has drawn some pushback from suburban commuters in the metropolitan area because it comes on top of existing tolls for crossing bridges and tunnels into the city.
Most drivers end up paying $9 to enter Manhattan south of Central Park on weekdays between 5 a.m. and 9 p.m. and on weekends between 9 a.m. and 9 p.m. The toll costs $2.25 during off hours for most vehicles.
New York officials have argued the program is helping to reduce traffic in the city and will eventually bring in billions of dollars for its subways, commuter trains and public buses.
FILE - Signs advising drivers of congestion pricing tolls are displayed near the exit of the Lincoln Tunnel in New York, Wednesday, Feb. 19, 2025. (AP Photo/Seth Wenig, File)
DUBAI, United Arab Emirates (AP) — U.S. President Donald Trump said Iran wants to negotiate with Washington after his threat to strike the Islamic Republic over its bloody crackdown on protesters, a move coming as activists said Monday the death toll in the nationwide demonstrations rose to at least 544.
Iran had no immediate reaction to the news, which came after the foreign minister of Oman — long an interlocutor between Washington and Tehran — traveled to Iran this weekend. It also remains unclear just what Iran could promise, particularly as Trump has set strict demands over its nuclear program and its ballistic missile arsenal, which Tehran insists is crucial for its national defense.
Meanwhile Monday, Iran called for pro-government demonstrators to head to the streets in support of the theocracy, a show of force after days of protests directly challenging the rule of 86-year-old Supreme Leader Ayatollah Ali Khamenei. Iranian state television aired chants from the crowd, who shouted “Death to America!” and “Death to Israel!”
Trump and his national security team have been weighing a range of potential responses against Iran including cyberattacks and direct strikes by the U.S. or Israel, according to two people familiar with internal White House discussions who were not authorized to comment publicly and spoke on condition of anonymity.
“The military is looking at it, and we’re looking at some very strong options,” Trump told reporters on Air Force One on Sunday night. Asked about Iran’s threats of retaliation, he said: “If they do that, we will hit them at levels that they’ve never been hit before.”
Trump said that his administration was in talks to set up a meeting with Tehran, but cautioned that he may have to act first as reports of the death toll in Iran mount and the government continues to arrest protesters.
“I think they’re tired of being beat up by the United States,” Trump said. “Iran wants to negotiate.”
He added: “The meeting is being set up, but we may have to act because of what’s happening before the meeting. But a meeting is being set up. Iran called, they want to negotiate.”
Iran through country's parliamentary speaker warned Sunday that the U.S. military and Israel would be “legitimate targets” if America uses force to protect demonstrators.
More than 10,600 people also have been detained over the two weeks of protests, said the U.S.-based Human Rights Activists News Agency, which has been accurate in previous unrest in recent years and gave the death toll. It relies on supporters in Iran crosschecking information. It said 496 of the dead were protesters and 48 were with security forces.
With the internet down in Iran and phone lines cut off, gauging the demonstrations from abroad has grown more difficult. The Associated Press has been unable to independently assess the toll. Iran’s government has not offered overall casualty figures.
Those abroad fear the information blackout is emboldening hard-liners within Iran’s security services to launch a bloody crackdown. Protesters flooded the streets in the country’s capital and its second-largest city on Saturday night into Sunday morning. Online videos purported to show more demonstrations Sunday night into Monday, with a Tehran official acknowledging them in state media.
In Tehran, a witness told the AP that the streets of the capital empty at the sunset call to prayers each night. By the Isha, or nighttime prayer, the streets are deserted.
Part of that stems from the fear of getting caught in the crackdown. Police sent the public a text message that warned: “Given the presence of terrorist groups and armed individuals in some gatherings last night and their plans to cause death, and the firm decision to not tolerate any appeasement and to deal decisively with the rioters, families are strongly advised to take care of their youth and teenagers.”
Another text, which claimed to come from the intelligence arm of the paramilitary Revolutionary Guard, also directly warned people not to take part in demonstrations.
“Dear parents, in view of the enemy’s plan to increase the level of naked violence and the decision to kill people, ... refrain from being on the streets and gathering in places involved in violence, and inform your children about the consequences of cooperating with terrorist mercenaries, which is an example of treason against the country,” the text warned.
The witness spoke to the AP on condition of anonymity due to the ongoing crackdown.
The demonstrations began Dec. 28 over the collapse of the Iranian rial currency, which trades at over 1.4 million to $1, as the country’s economy is squeezed by international sanctions in part levied over its nuclear program. The protests intensified and grew into calls directly challenging Iran’s theocracy.
Nikhinson reported from aboard Air Force One.
In this frame grab from video obtained by the AP outside Iran, a masked demonstrator holds a picture of Iran's Crown Prince Reza Pahlavi during a protest in Tehran, Iran, Friday, January. 9, 2026. (UGC via AP)
In this frame grab from footage circulating on social media from Iran shows protesters taking to the streets despite an intensifying crackdown as the Islamic Republic remains cut off from the rest of the world in Tehran, Iran, Friday, Jan. 9, 2026.(UGC via AP)
In this frame grab from footage circulating on social media from Iran showed protesters once again taking to the streets of Tehran despite an intensifying crackdown as the Islamic Republic remains cut off from the rest of the world in Tehran, Iran, Saturday Jan. 10, 2026. (UGC via AP)
