Bursting an “EO” Myth?
Two weeks into the new term, a Seattle courtroom offered the year’s defining image of presidential power meeting its limits: a Ninth Circuit panel upheld a nationwide block on the administration’s attempt to curtail birthright citizenship, acknowledging that the judges’ interpretation of the Constitution—not a presidential pen stroke—sets the terms of American membership.
Weeks earlier, in Baltimore, a federal judge had temporarily enjoined key parts of two DEI-related executive orders as both vague and speech-burdening—an early reminder that even marquee directives can stall at the courthouse door—before the Fourth Circuit stayed that injunction while the appeal plays out.
More than half of the administration’s major orders this year hit a judicial roadblock, often within weeks. And the action has hardly been confined to the usual venues: the administration even took the extraordinary step of suing all 15 federal judges in Maryland over a deportation-related order—only to see the case tossed. The result is a litigation map that runs through Washington, D.C., Seattle, and Baltimore as reliably as it does through Texas, with trial and appellate courts asked—again and again—to decide how far executive power can go on contact with statute and Constitution.
The Supreme Court, for its part, has signaled that the outer edge of that power will be tested in cases now moving onto its docket—an arena where campaign-trail ambition meets Article II in full daylight.
In other words, the myth of the instant, untouchable executive order collided this year with a more grounded reality: in a polarized moment, the federal judiciary has become the first responder to the biggest policy fights, not as a partisan counterforce but as the system’s built-in referee.
This trend highlights a new reality of American governance: in an era of congressional gridlock, courts are where politics move next. In the past this placed courts as a main engine creating policy in the void of action by Congress and Executive. Now Trump seems to have acknowledged this vacuum and has taken the reins on action from both Congress and the courts.
EOs now serve as a President’s bid to deliver fast policy wins to their base, but the opposition (state attorneys general, advocacy groups, and even some businesses) now reflexively races to court to halt those policies. The result is that the ultimate fate of many high-profile EOs is decided by judges, not just by the stroke of a pen. Far from being all-powerful, executive orders in 2025 were immediately pulled into a political-legal tug-of-war, demonstrating that when it comes to major policies, the President’s power is checked early and often by the courts.
To dig into this area of litigation, this article analyzes a comprehensive dataset of 327 federal district court cases challenging executive orders issued through the first half of August 2025. This “EO Litigation Tracker” captures each case’s issue area, the presiding judge and their appointing president, the relief sought (Temporary Restraining Order or Preliminary Injunction), whether an injunction was granted (and if so, whether it was nationwide in scope), and the outcome (whether the EO was upheld or enjoined in the end). By categorizing cases by policy issue and by the type/scope of injunctive relief, patterns emerged that tell a political story: which issues provoked the most legal battles, and where (and before whom) those battles played out. The Tracker also groups cases by the court’s location (circuit) and by each presiding judge’s background to see how ideological leanings might have influenced results. This article focuses on the judicial dimensions of these decisions. A second article will emphasize policy area where orders are under judicial scrutiny.
Who Decides?
This chart shows that most EO cases in 2025 were decided by judges appointed by Barack Obama (105) and Joseph R. Biden Jr. (78)—together, well over half of the total shown. Donald Trump (44), William J. Clinton (40), and George W. Bush (35) appointees handled a smaller but still substantial share, while Reagan (15), George H. W. Bush (3), and Carter (2) trailed. The skew reflects where plaintiffs filed—especially D.D.C. and coastal circuits—more than any single judge’s ideology, and it helps explain why many outcomes tilted against the administration; the figure omits judges that were nominated by one president and held over for confirmation under another president.
The graph above tracks case outcomes by the appointing president of the presiding judge. Trump and Obama appointees show the largest upheld slices, but even there, injunctions still outnumber affirmances. Reagan, Clinton, and Biden appointees have only slivers of upheld EOs while George H. W. Bush (and to a lesser extent Reagan and George W. Bush) appointees have comparatively larger dismissal shares. The pattern suggests judges’ political backgrounds and ideology matters at the margins, but the prevailing story is broad judicial skepticism of the orders at the interim stage regardless of who appointed the judge.
By mid-2025, the administration lost far more than it won. Of the 274 cases that reached a clear outcome in 2025, 232 (approximately 85%) enjoined the EO or related agency action in whole or part, while 42 (15%) upheld it. Party-of-appointing-president mattered, but not enough to save most orders. Democratic appointees ruled against the EO about 88% of the time; Republican appointees did so about 77% of the time. On early relief, Democratic appointees granted preliminary injunctions in roughly 60% of cases, compared with about 42% for Republican appointees. The gap tracks expectations—but the striking fact is how often judges from both camps found legal defects serious enough to sink the orders.
The trend isn’t new—and it cuts both ways. Analyses show that most nationwide injunctions (before the Supreme Court essentially prohibited them in Trump v. CASA) against both Trump’s first term and Biden’s administration came from judges appointed by the opposite party. Policy fights are increasingly resolved through legal briefs and emergency motions, with courtroom wins and losses carrying the weight—and the political aftershocks—of legislative victories or defeats.
The Emerging Pattern
The biggest driver wasn’t just ideology; it was where the lawsuits were filed. The District of Columbia was ground zero: 104 of 327 cases—just over 30%—ran through D.D.C.. That’s logical and strategic. National policies are administered in Washington, the judges there are steeped in administrative law, and both government and public-interest lawyers know the forum well. Blue-state venues like the Northern District of California, the District of Massachusetts, and the District of Maryland also drew heavy fire, reflecting plaintiffs’ choices to file where they expected a receptive ear to statutory and APA arguments.
Texas—the star of nationwide policy fights under the prior administration—was relatively quiet. The Fifth Circuit (Texas, Louisiana, Mississippi) accounted for only 12 cases (approximately 3.7%), while the Ninth Circuit saw 53 (approximately 16%) and the First Circuit logged 43. In a role-reversal, liberal states and advocacy groups led the charge in 2025 and steered cases to D.C., California, and the Northeast rather than to Texas.
Inside those busy forums, repeat players mattered. In D.D.C., judges such as Paul Friedman, John Bates, Rudolph Contreras, and Timothy Kelly handled multiple EO cases. Despite different appointing presidents, they often converged on results—frequently enjoining or striking down orders when they viewed defects as obvious (conflicts with statute, APA shortcuts, or shaky authority).
Executive orders set the agenda, but judges set the bounds. In 2025, venue strategy and ideology shaped the skirmishes, yet basic law resolved the disputes for the time being. With the Supreme Court poised to refine the rules, any presidency should expect its biggest EOs to face the courtroom first.
** This work would not be possible without the inimitable assistance of Daniel Thompson.
Click here to read more from Legalytics…
Adam Feldman runs the litigation consulting company Optimized Legal Solutions LLC. Check out more of his writing at Legalytics and Empirical SCOTUS. For more information, write Adam at adam@feldmannet.com. Find him on Twitter: @AdamSFeldman.
The post Rule By Lawsuit: Inside 2025’s Executive-Order Wars appeared first on Above the Law.
Two weeks into the new term, a Seattle courtroom offered the year’s defining image of presidential power meeting its limits: a Ninth Circuit panel upheld a nationwide block on the administration’s attempt to curtail birthright citizenship, acknowledging that the judges’ interpretation of the Constitution—not a presidential pen stroke—sets the terms of American membership.
Weeks earlier, in Baltimore, a federal judge had temporarily enjoined key parts of two DEI-related executive orders as both vague and speech-burdening—an early reminder that even marquee directives can stall at the courthouse door—before the Fourth Circuit stayed that injunction while the appeal plays out.
More than half of the administration’s major orders this year hit a judicial roadblock, often within weeks. And the action has hardly been confined to the usual venues: the administration even took the extraordinary step of suing all 15 federal judges in Maryland over a deportation-related order—only to see the case tossed. The result is a litigation map that runs through Washington, D.C., Seattle, and Baltimore as reliably as it does through Texas, with trial and appellate courts asked—again and again—to decide how far executive power can go on contact with statute and Constitution.
The Supreme Court, for its part, has signaled that the outer edge of that power will be tested in cases now moving onto its docket—an arena where campaign-trail ambition meets Article II in full daylight.
In other words, the myth of the instant, untouchable executive order collided this year with a more grounded reality: in a polarized moment, the federal judiciary has become the first responder to the biggest policy fights, not as a partisan counterforce but as the system’s built-in referee.
This trend highlights a new reality of American governance: in an era of congressional gridlock, courts are where politics move next. In the past this placed courts as a main engine creating policy in the void of action by Congress and Executive. Now Trump seems to have acknowledged this vacuum and has taken the reins on action from both Congress and the courts.
EOs now serve as a President’s bid to deliver fast policy wins to their base, but the opposition (state attorneys general, advocacy groups, and even some businesses) now reflexively races to court to halt those policies. The result is that the ultimate fate of many high-profile EOs is decided by judges, not just by the stroke of a pen. Far from being all-powerful, executive orders in 2025 were immediately pulled into a political-legal tug-of-war, demonstrating that when it comes to major policies, the President’s power is checked early and often by the courts.
To dig into this area of litigation, this article analyzes a comprehensive dataset of 327 federal district court cases challenging executive orders issued through the first half of August 2025. This “EO Litigation Tracker” captures each case’s issue area, the presiding judge and their appointing president, the relief sought (Temporary Restraining Order or Preliminary Injunction), whether an injunction was granted (and if so, whether it was nationwide in scope), and the outcome (whether the EO was upheld or enjoined in the end). By categorizing cases by policy issue and by the type/scope of injunctive relief, patterns emerged that tell a political story: which issues provoked the most legal battles, and where (and before whom) those battles played out. The Tracker also groups cases by the court’s location (circuit) and by each presiding judge’s background to see how ideological leanings might have influenced results. This article focuses on the judicial dimensions of these decisions. A second article will emphasize policy area where orders are under judicial scrutiny.
This chart shows that most EO cases in 2025 were decided by judges appointed by Barack Obama (105) and Joseph R. Biden Jr. (78)—together, well over half of the total shown. Donald Trump (44), William J. Clinton (40), and George W. Bush (35) appointees handled a smaller but still substantial share, while Reagan (15), George H. W. Bush (3), and Carter (2) trailed. The skew reflects where plaintiffs filed—especially D.D.C. and coastal circuits—more than any single judge’s ideology, and it helps explain why many outcomes tilted against the administration; the figure omits judges that were nominated by one president and held over for confirmation under another president.
The graph above tracks case outcomes by the appointing president of the presiding judge. Trump and Obama appointees show the largest upheld slices, but even there, injunctions still outnumber affirmances. Reagan, Clinton, and Biden appointees have only slivers of upheld EOs while George H. W. Bush (and to a lesser extent Reagan and George W. Bush) appointees have comparatively larger dismissal shares. The pattern suggests judges’ political backgrounds and ideology matters at the margins, but the prevailing story is broad judicial skepticism of the orders at the interim stage regardless of who appointed the judge.
By mid-2025, the administration lost far more than it won. Of the 274 cases that reached a clear outcome in 2025, 232 (approximately 85%) enjoined the EO or related agency action in whole or part, while 42 (15%) upheld it. Party-of-appointing-president mattered, but not enough to save most orders. Democratic appointees ruled against the EO about 88% of the time; Republican appointees did so about 77% of the time. On early relief, Democratic appointees granted preliminary injunctions in roughly 60% of cases, compared with about 42% for Republican appointees. The gap tracks expectations—but the striking fact is how often judges from both camps found legal defects serious enough to sink the orders.
The trend isn’t new—and it cuts both ways. Analyses show that most nationwide injunctions (before the Supreme Court essentially prohibited them in Trump v. CASA) against both Trump’s first term and Biden’s administration came from judges appointed by the opposite party. Policy fights are increasingly resolved through legal briefs and emergency motions, with courtroom wins and losses carrying the weight—and the political aftershocks—of legislative victories or defeats.
The biggest driver wasn’t just ideology; it was where the lawsuits were filed. The District of Columbia was ground zero: 104 of 327 cases—just over 30%—ran through D.D.C.. That’s logical and strategic. National policies are administered in Washington, the judges there are steeped in administrative law, and both government and public-interest lawyers know the forum well. Blue-state venues like the Northern District of California, the District of Massachusetts, and the District of Maryland also drew heavy fire, reflecting plaintiffs’ choices to file where they expected a receptive ear to statutory and APA arguments.
Texas—the star of nationwide policy fights under the prior administration—was relatively quiet. The Fifth Circuit (Texas, Louisiana, Mississippi) accounted for only 12 cases (approximately 3.7%), while the Ninth Circuit saw 53 (approximately 16%) and the First Circuit logged 43. In a role-reversal, liberal states and advocacy groups led the charge in 2025 and steered cases to D.C., California, and the Northeast rather than to Texas.
Inside those busy forums, repeat players mattered. In D.D.C., judges such as Paul Friedman, John Bates, Rudolph Contreras, and Timothy Kelly handled multiple EO cases. Despite different appointing presidents, they often converged on results—frequently enjoining or striking down orders when they viewed defects as obvious (conflicts with statute, APA shortcuts, or shaky authority).
Executive orders set the agenda, but judges set the bounds. In 2025, venue strategy and ideology shaped the skirmishes, yet basic law resolved the disputes for the time being. With the Supreme Court poised to refine the rules, any presidency should expect its biggest EOs to face the courtroom first.
** This work would not be possible without the inimitable assistance of Daniel Thompson.
Click here to read more from Legalytics…
Adam Feldman runs the litigation consulting company Optimized Legal Solutions LLC. Check out more of his writing at Legalytics and Empirical SCOTUS. For more information, write Adam at [email protected]. Find him on Twitter: @AdamSFeldman.
