‘Shaking in Their Boots’: Trump Wanted a Portland-Style Offensive in Chicago

In the week leading up to his announcement of a “surge” of hundreds of FBI, Justice Department, and Homeland Security personnel to Chicago, Donald Trump wanted a bigger, more public, more violent fight on the streets of the Windy City.

According to three people familiar with the president’s private remarks, Trump previously envisioned an ostentatious, camera-ready show of force. He wanted to go after what he saw as violent gang leaders, flush them out of hiding in ways that would have them “shaking in their boots” like they never had before, and have alleged perpetrators marched out in front of the news cameras. Violent crime has long plagued Chicago, and murders are spiking to highs not seen in decades. But Trump insisted that with the right leader, and the right muscle, crime there could be reduced “very quickly.”

The president said he wanted something similar to what his administration has done in Portland, an ongoing melee between protesters and rioters and unmarked federal authorities. Trump has been closely monitoring the conflict—largely on his favorite channel, Fox News—and trumpeting it as a sign of his own supposed strength.

But by the time Wednesday afternoon came, the president, Attorney General William Barr, and other administration brass had settled—at least for now—on something less overt that they could sell to the American people: an expansion of Operation Legend, a DOJ-driven law-and-order initiative that administration officials have gone out of their way to stress is distinct from the vicious federal intervention led by DHS in Portland.

Trump ‘Surges’ Feds to Chicago Like It’s a War Zone

“The president takes law and order as seriously as he does his promises on jobs and immigration. It’s fundamental to his presidency,” a senior Trump administration official said on Thursday afternoon. “And at the same time, there are constant bureaucratic elements we have to weigh to make sure our response is both effective and legally sound.”

U.S. officials and sources close to the White House say that, the leader of the free world’s outbursts in meetings and phone conversations notwithstanding, there wasn’t a widespread appetite in the administration to replicate a Portland-style crackdown on the streets of Chicago, with several officials conceding that doing so would most likely not solve the city’s problems with gang violence and instead exacerbate the situation. The officials also noted that an effort to do so would almost certainly result in extreme backlash and hellishly bad PR.

One White House official sought to downplay Trump’s recent musings on a larger show of force, telling The Daily Beast on Wednesday that it was largely the president “letting off steam.”

Those who’ve been close to Trump over the years see a familiar pattern: a president who so often demands large-scale, draconian, and potentially disastrous action, with senior officials actively working to temper, or inflame, those desires. Sometimes, the president follows through. Other times, he’s easily talked down by aides, backs off for fear of the nasty publicity, or simply gets bored and forgets about it entirely.

“There was rarely a time I spoke to him about violent crime when two things didn’t come up: Number One, that it’s all happening in Democrat-run cities, with Chicago being shorthand for that kind of [blight],” said one former senior Trump administration official. “And Number Two, if it were up to him, we would return to the old days where it was eye-for-an-eye, tooth-for-a-tooth—or we would forget about proportionality altogether. He would talk about lining up drug dealers and gang members in front of a firing squad... If it were solely up to him, that is how the country would solve crime in Democrat-run cities [such as Chicago and Detroit].”

Of course, heavy-handed tactics have been tried—over and over again—on the streets of Chicago. The city’s murder rate remains perniciously high. Local attorneys and activists told The Daily Beast that a federal plus-up of forces isn’t the answer.

“We can see from what happened in Portland that what these secret police do only exacerbates the situation. It’s a complete disregard for the human and constitutional rights of protesters, and it’s a racist political gambit Trump is doing in desperation because he’s losing in the polls,” Flint Taylor, the Chicago attorney who has spent decades litigating against police violence, told The Daily Beast on Tuesday.

The current op in Chicago is billed as relatively restrained, compared to the chaos and clampdown in Portland. But it is still causing serious consternation among certain senior government and military officials, who still wince at the blowback from Trump’s mission to “dominate” American cities last month and who want nothing to do with the operation this time around.

Operation Legend is a Department of Justice initiative that focuses on cracking down on violent crime, specifically gun violence, in America’s cities. It launched earlier this month in Kansas City and is expanding now to Chicago and Albuquerque, New Mexico. In his announcement with the president Wednesday, Barr said the department expects to surge resources to local and state police departments in a slew of cities in the coming weeks in months. The exact details of how these DOJ law enforcement personnel will work to combat crime remain murky, though Barr has said the individuals working on Operation Legend will mostly work in the capacity as investigators and will not occupy the streets as those Department of Homeland Security officers have in Portland.

Senior Pentagon officials said they had not been asked to participate in either Operation Legend or in the response to protests in Portland. National Guard officials in Chicago, though, were wary of Trump-Barr announcement Wednesday, telling The Daily Beast that their troops “wouldn’t participate” in assisting Operation Legend task forces unless under explicit direction from the governor. “And that’s not something the state is going to do right now,” one of those officials said. “There are a whole host of legal issues that come up with this. And every couple of years we will hear the administration say, ‘We’re going to send in the feds to Chicago,’ and it always causes a headache.”

Without considerable buy-in in from the state and local governments, the administration will have a difficult time selling the surge of federal law enforcement officers to the American people, said John Cohen, former deputy undersecretary for intelligence and analysis at DHS.

“It’s highly problematic if federal personnel are deployed— even if it falls into their responsibilities—if they operate outside of the command and control that’s been put in place on the local level,” Cohen said. “If people aren’t in communication, you introduce a level of volatility into the environment and you undermine the relationship that has to exist on the ground between the federal and state authorities.”

“Joe Biden and the Democrats would normalize the string of violence and destruction we’ve seen from their supporters instead of stand up to it,” Trump campaign spokeswoman Samantha Zager said in a statement to The Daily Beast. “President Trump will continue to enforce law and order to protect the fabric of our nation, even as Democrats do everything in their power to avoid holding these criminals accountable.”

Team Trump has sought for months to paint his Democratic rival, former Vice President Joe Biden, as both too soft on crime and, in his past, far too tough on crime, to the point that he helped forge the racial and criminal-justice hellscape we’re still trying to escape today. President Trump himself has suffered from that very dual impulse, where earlier this summer he began to portray himself as the true criminal-justice reformer in the race, only to quickly abandon it in favor of going all-in on dark, “law and order” flamboyance.

Who Actually Wants Trump to Send in the Feds? Police Unions.

Earlier this week, a senior administration official dubbed the current moment “President Trump’s war on crime and lawlessness,” explaining that the new initiatives would go well beyond the scope of merely protecting lifeless statues and federal property. “The president sees the two as different parts of the same fight,” this official added, regarding the election-year pivot from a statue-based pretext to one focused largely on other crimes and gang violence.

A solid majority of the reputable public polling shows that, if anything, Trump’s current posturing and his federal crackdowns have only helped tank his numbers, with less than four months to go until the November election that will decide if it’s his fate to be a one-term “loser.”

“Those lives in Chicago should matter; you cannot allow this,” said Armstrong Williams, a longtime adviser to Trump’s HUD secretary Ben Carson. “The message is not about if Donald Trump is the president, the message should be about how we are not going to allow Chicago to be taken over by gang warfare... Sometimes, desperate times call for desperate measures… Sometimes, you need someone to stand up to the bully and say, ‘I’m a bigger bully and I have a bigger gun.’”

—with additional reporting by Spencer Ackerman

Read more at The Daily Beast.

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