It should come as no surprise that President Trump has been counting on his use of the court system to allow his administration to pursue his objectives despite legal challenges. Donald Trump and his businesses are not novices when it comes to using the court system to their advantage. Since 1973, Donald Trump’s businesses have been involved in over 4,000 federal and state legal cases. The cases run the gamut from real estate issues to personal defamation. His businesses have been involved in over 100 tax cases. In 2022 the Trump Organization was convicted on 17 criminal charges. (Jacobs, Shayna, “Trump Organization Convicted in N.Y. Criminal Tax Fraud Trial,” Washington Post, December 6, 2022). Donald Trump has been to court for accusations of sexual harassment and assault. The E. Jean Carrol case decision founds him guilty and fined him $80 million. (Stempel, Jonathan, “US Judge Upholds 83.3 Million Defamation Loss, Rejects New Trial,” Reuters, April 25, 2024). In January 2023, he was fined nearly $1 million because the judge found him to be “a prolific and sophisticated litigant who repeatedly using the courts to seek revenge on political adversaries. Haberman, Maggie (January 31, 2023) “Trump’s Well-Worm Legal Playbook Starts to Look Frayed,” Vanity Fair.
While many MAGA supporters would say that the Democrats have used the justice system to persecute Donald Trump, his record of problems with the government, other businesses, and people precede his interest in politics by several decades. Most cases in which Donald Trump has been involved were before he announced his candidacy for President.
Still, since January 2025, hundreds of lawsuits have been filed against the current Trump administration. These lawsuits challenge various executive orders and actions taken by the administration, including those by the Department of Government Efficiency (DOGE) led by Elon Musk. The courts have blocked the administration in several cases, and many of these cases are currently under appeal.
A litigation tracker by Just Security has recorded a total of 378 cases against the Trump administration’s actions. Out of these, 25 actions have been blocked, 77 temporarily blocked, and 17 blocked pending appeal. Additionally, 146 cases are still awaiting court rulings.
One notable case is Taylor v. Trump, where a group of individuals whose federal death sentences were commuted by President Biden are challenging an executive order by President Trump. This order directed the Attorney General to evaluate their imprisonment conditions and resulted in their indefinite incarceration at a federal supermax prison. Other significant cases where his efforts have been blocked include a legal challenge to a birthright citizenship executive order and challenges to suspending his asylum executive order. Immigration advocacy groups argue that the executive order violates the Constitution. Other cases where bans on executive orders are in place include challenges to suspending the Refugee Program. Plaintiffs argue that the executive order violates the Fifth Amendment. A federal appeals court ruled in March that Trump can partially enforce the refugee ban. And another case fights the Deportation of the Boulder, Colorado attack suspect’s family. A federal judge in Colorado halted the deportation of the wife and five children of Mohamed Soliman, who is facing a hate crime charge in the wake of a firebombing attack in Colorado. The ruling will remain in effect until a scheduled hearing. While President Trump has had his actions challenged and blocked, he has also had success with the Supreme Courts decision on Executive Immunity and most recently in the civil judgement in New York where the fine of $50 million for fraud was overturned by the appellate court.
Summary of Total number of cases currently tracked by Just Security: 381.
Case Status Summary:
Case Closed in Favor of Plaintiff: 1
Blocked: 25 (When a case is described as “blocked,” it means that a court has issued an order preventing the enforcement or implementation of a specific action or policy. This can happen for various reasons, such as the court finding that the action or policy is likely to be unconstitutional, violates existing laws, or causes irreparable harm.)
Temporarily Blocked: 77
Blocked Pending Appeal: 17
Temporarily Blocked in Part or Temporary Block Denied in Part: 11
Temporary Block Denied: 38
Not Blocked, Pending Appeal: 34
Awaiting Court Ruling: 147
Case Closed: 22
Misc: Transferred: 2
Case Closed/Dismissed in Favor of Government: 7
The End Game
For over 50 years, Donald Trump has used the courts, mostly to his advantage. When a court finds against his position, he appeals. If the appeal fails, he appeals to the next higher court. This is a delaying tactic that often results in a settlement where Donald Trump can claim a victory even if it costs him. The tactic has allowed him time to proceed with his agenda while the legality plays out in court. To improve his chances of favorable outcomes, he has discovered a tactic to appoint judges who are loyal to him to positions where he may have cases heard. In an Augst 19, 2025 article in Politico, Erica Orden notes that President Trump is circumventing the Senate to install top federal prosecutors who are loyalists. According to Orden, when Trump’s nominees can’t be confirmed by the Senate, he temporarily installs an interim US Attorney. This person can serve for 120 days (4 months). When the term ends, District Judges can reject the appointment. The Trump administration has chosen to ignore the District Judges and reappoint his selected federal attorney for an additional 120 days (Orden, Erica, “Trump Bypasses the Senate—and the Courts—to install loyal US Attorneys,” Politico, August 19, 2025).
One of the most recent cases involved New Jersey, where Alina Habba, one of Trumps personal lawyers was appointed to serve and then nominated for the permanent position of federal prosecutor. Habba was the attorney involved in the detention of Newark Mayor Ras Baraka and Representative LaMonica McIver when they attempted to visit an immigration detention center (Catalini, Mike, “Judge Says Former Trump Lawyer Alina Habba has been Unlawfully Serving as US Attorney in New Jersey,” Associated Press, August 19, 2025). On August 20, 2025, US District Judge Matthew Brann ruled that Habba was acting Illegally as the US attorney for New Jersey. President Trump’s illegal effort to bypass Congress was noted by the Judge. Cases overseen by Habba after her illegal appointment are now being appealed by defendants in those cases (Rivard, Ry, “The Fallout from the Alina Habba Ruling has Begun” Politico, August 22, 2025).
Conclusion
How the battle for the courts will play out is anyone’s guess. However, it is worth noting that President Trump’s team, even with its delaying tactics is losing more often than winning. The issue to be considered is the damage done to the system and the agencies impacted by the administration actions while the courts decide whether the actions are Constitutional!
Thoughts from the Middle by Robert J. Fischer 