On August 25, 2025, President Donald Trump signed two executive orders targeting long-standing issues tied to crime and public safety, aiming to dismantle cashless bail policies and crack down on flag burning. The first order seeks to eliminate cashless bail in Washington, D.C., and threatens to withhold federal funding from other jurisdictions that maintain such policies, which allow defendants to be released without paying bail while awaiting trial. Trump, decrying cashless bail as a “disaster” that fuels crime, emphasized its end in D.C. through federalization, claiming it has allowed dangerous offenders back onto the streets. Critics, including groups like The Bail Project, argue that cashless bail addresses inequities for low-income defendants and point to data showing no significant crime spike in jurisdictions like D.C., which adopted the policy in the 1990s, or Illinois, which eliminated cash bail in 2023.

The second executive order directs the Department of Justice, under Attorney General Pam Bondi, to pursue prosecutions for flag burning, despite the 1989 Supreme Court ruling in Texas v. Johnson that protects such acts as free speech under the First Amendment. Trump’s order instructs the DOJ to investigate flag desecration cases, focusing on state and local laws that might apply, and even calls for denying visas or immigration benefits to noncitizens involved in such acts. The administration argues that flag burning incites violence and is “uniquely offensive,” though legal experts warn the order may face significant constitutional challenges. Trump’s push for a one-year prison penalty for flag burning has sparked debate, with supporters on platforms like X praising his defense of national symbols, while others see it as an assault on free expression.

These orders are part of Trump’s broader “tough-on-crime” agenda, which includes federalizing D.C.’s police and deploying National Guard troops to address what he describes as rampant lawlessness in Democratic-run cities. The cashless bail order also tasks law enforcement with holding D.C. arrestees in federal custody to bypass local policies, a move Trump claims is necessary to protect residents and federal workers. However, opponents argue these actions overstep federal authority and ignore evidence, like D.C.’s 30% crime drop since 2023, while escalating tensions in urban centers. With plans to extend similar measures to cities like Chicago, Trump’s executive actions signal a confrontational approach to reshaping criminal justice, though their legal and practical success remains uncertain amid likely court challenges.