The Cornering Strategy: Trump Orders End to Cashless Bail in DC, Offers Nat’l Guard in Chicago

Bill Clinton employed a triangulation strategy to co-opt Republican voters. Donald Trump has spent the first seven months of his presidency employing a cornering strategy. Trump has used his bully pulpit — perhaps in the most literal sense since the Roosevelts — to force Democrats to corner themselves onto the fringe positions on issues that matter most to American voters.

This month, Trump has used executive action on crime to force Democrats to side with criminals. He’s about to force them to double down with his latest move to end cashless bail in Washington DC, and his efforts to use federal funding to leverage the same change across the country:

🚨 BREAKING: President Trump just signed an executive order WITHHOLDING federal funding for states and cities using cashless bail

“Cashless bail… that was when the big crime in this country started”

“They KlLL people and they get out. Cashless bail. They thought it was… pic.twitter.com/14vKFGMTOI

— Nick Sortor (@nicksortor) August 25, 2025

One order from Trump directs Attorney General Pam Bondi to identify federal funds that could be suspended or eliminated in states and local jurisdictions with cashless bail policies. He and his administration sees such policies as overly lenient; others view them as central to preventing discrimination in the criminal justice system based on wealth.

Trump instructed specific focus on D.C., where his administration is exerting unprecedented federal control. His order told law enforcement officials to pursue pretrial detention whenever possible and withhold money and federal services if the city continues to allow defendants to be released without posting bail.

The U.S. does not have a single bail system. A patchwork of state laws and local court rules regulate who is eligible for pretrial release and when. The District, for example, has prohibited cash bonds for decades and releases some defendants without requiring any future promise of financial payment.

The “specific focus” will likely succeed, since — despite Protection Racket Media hyperventilation — the federal government has jurisdiction and authority to set such policies. Generally speaking, it’s better to have Congress deal with these issues, but Congress ceded its authority to ‘home rule’ in the district decades ago. Cashless bail is a policy imposed by the city council, not by federal statute, and Trump can supersede such policies in the district. If Congress wants to restore cashless bail, it can act — but even Democrats are starting to figure out that it’s a loser in today’s higher-crime environment in urban areas. 

Politico notes that today as well:

Democrats in support of bail reforms have faced campaign difficulties as Republicans continue to hammer them for being “radical” and “soft” on crime.

In 2022, New York Democrats scaled back their support for cashless bail after losing county office seats and facing warning signals in states like Illinois and California.

So don’t expect House Democrats to take the bait in advance of the midterm elections. However, Democrats elsewhere will leap to fight the White House on the loss of federal funds for refusing to shed cashless-bail policies in urban centers and blue states. They will argue — with some justification — that Trump lacks the authority and jurisdiction to force such policy changes in state and local courts, and judges will likely tie up such efforts for months. 

That won’t matter to Trump, and neither will the fights he can expect from his claim to be readying the National Guard for law-enforcement missions in Chicago, San Francisco, and elsewhere:

One of the president’s executive orders also directs the defense secretary to ensure that each state’s National Guard is resourced, trained, organized and available to help in “quelling civil disturbances,” and directs the defense secretary to designate a number of each state’s National Guard to be available for such purposes. Mr. Trump has said Chicago could be the next city where the federal government imposes a crime crackdown. 

“We’re ready to go anywhere,” the president said when asked about Chicago. “We can go anywhere on less than 24 hours’ notice.”

That will almost certainly not happen. Trump could deploy the National Guard to help the DC police to enforce the law because the federal government has jurisdiction over DC. It’s not a state, so it has no sovereign considerations. To deploy National Guard troops in Chicago, Trump would have to get permission/an invitation from Illinois governor J.B. Pritzker, who wouldn’t agree to that in a million years. The same is true in San Francisco with Gavin Newsom, and so on. 

Trump knows this, of course, and so do Pam Bondi, Pete Hegseth, et al. What Trump wants with both policies, though, is to bait Pritzker, Newsom, and other Democrat leaders into a fight where they have to defend lawlessness and crime. Furthermore, the success thus far of the National Guard mission in DC — where no murders have taken place in almost two weeks now — creates a sharp contrast to the progressive policies in other blue-city and blue-state jurisdictions where crime is out of control. Trump is cornering Democrats into doubling down on their failed progressive governance … and so far is succeeding at it, too. 

When Salena Zito warned people to take Trump seriously rather than literally, this is precisely what she meant. Democrats are still falling for this cornering strategy, and in fact are getting worse at recognizing it, because they think shrieking over Trump matters more than fixing the real problems their failed policies have created. One has to wonder what it will take for Democrats to break this spell, but don’t expect them to wake up and smell the coffee burning any time soon. 

Note: David Strom will have more on Trump’s efforts to criminalize flag-burning later this evening. 

Editor’s Note: President Donald Trump is returning Washington, D.C. to the American people by locking up violent criminals and restoring order. 

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