What are the most significant lawsuits Donald Trump has been involved in since 2019?

1. A Historic Criminal Conviction That Changed the Legal Landscape

Donald Trump was convicted on May 30, 2024, of 34 counts of falsifying business records in New York relating to hush-money payments, making him the first former U.S. president convicted of criminal charges; sentencing was scheduled and appeals were anticipated ^{[2] [1]}. That conviction stands apart because it produced a definitive guilty verdict after a high-profile trial, and it shapes criminal-exposure calculations for other matters by demonstrating that a jury can convict on complex business-records theories even involving a former president. The New York case is concrete in outcome compared with many other matters that remain in pretrial or appellate postures, and it has spawned extensive legal and political debate about precedent, punishment, and campaign implications, while appeals promise more litigation and potential legal uncertainty ahead ^[2].

2. Multiple Election-Related Prosecutions That Remain Central and Contentious

Since 2019, the most significant ongoing criminal actions against Trump include federal charges in Washington, D.C., and state charges in Georgia alleging schemes to overturn the 2020 presidential election; these matters together account for a substantial portion of Trump’s criminal exposure and remain deeply contested through motions, pretrial litigation, and overlapping constitutional questions ^{[1] [5]}. The D.C. case focuses on efforts to obstruct the certification of the election, while the Georgia case centers on alleged conduct to interfere with that state’s results; both involve felony allegations and complex evidentiary fights. Courts have repeatedly grappled with separation-of-powers and immunity arguments in these prosecutions, and judges have issued rulings that leave core counts intact even as defendants press aggressive defenses — demonstrating that these cases are legally weighty and politically consequential ^{[1] [5]}.

3. Classified-Documents Case and Related Federal Litigation: A Mixed Record of Rulings

A federal prosecution over the retention of classified documents at Mar-a-Lago and alleged obstruction produced a major litigation arc: indictment on multiple counts, intense discovery and privilege disputes, and a significant judicial decision dismissing the case in mid-2024 which the Department of Justice appealed ^[5]. That sequence illustrates how procedural rulings, evidentiary doctrines, and post-election developments can produce uneven fortunes: the government secured an indictment and pursued charges aggressively, yet a court’s dismissal created a legal setback for prosecutors that the DOJ then challenged on appeal. The documents case therefore remains a pivotal example of how high-stakes criminal prosecutions against former officials can pivot on narrow legal doctrines and appellate review, leaving ultimate resolution contingent on higher-court rulings ^{[5] [2]}.

4. Large Civil Judgments and Business-Law Troubles That Carry Financial Weight

Civil litigation has produced substantial monetary judgments against Trump and his businesses, most notably a $454 million civil fraud penalty and earlier findings in separate defamation and fraud suits, such as E. Jean Carroll’s award and corporate penalties tied to business practices ^{[2] [3]}. These financial rulings implicate corporate governance, valuation practices, and state regulatory power, and they have triggered appeals and complex enforcement fights over asset remedies and bond requirements. Civil outcomes differ from criminal liability in remedy and standard, but the size of these judgments—paired with the Trump Organization’s separate corporate penalties and fines—creates real economic consequences, complicates fundraising and liquidity calculations, and ensures prolonged litigation across trial and appellate courts ^{[2] [3]}.

5. Administrative and Policy Litigation: A Wave of 2025 Suits Challenging Government Actions

Beyond personal criminal and civil matters, the Trump administration and related actors faced an array of administrative-policy lawsuits alleging unlawful rulemaking and executive action, including litigation brought by states over withheld education funds and federal policies on immigration, media, and diversity programs that courts blocked or enjoined in 2025 ^{[6] [4]}. In April–July 2025, courts issued a string of rulings striking down or pausing initiatives on voting, DEI policies, sanctuary-city funding, and agency restructuring, reflecting judges’ scrutiny of statutory and constitutional limits on executive power. These cases are procedurally distinct from personal prosecutions but are politically salient because they affect governance and program delivery; they show how litigation can serve as a check on abrupt policy shifts, and they illustrate the bipartisan nature of some judicial pushback referenced in recent reporting ^{[4] [6]}.

Sources: summaries and timelines synthesized from the provided analyses ^{[6] [4] [2] [7] [8] [1] [3] [5]}.