Fact check: How many lawsuits has Donald Trump won or lost in his lifetime?

1. What the dossier claims about Trump’s wins — settlements and dismissals that look like victories

The assembled items emphasize several instances framed as legal wins for Trump: eight-figure settlements with major broadcasters and favorable dismissals or procedural rulings in some suits. For example, the dossier notes eight-figure settlements against ABC and CBS within a recent period and that a federal judge in Montana dismissed a climate lawsuit against Trump for lack of standing, described as a legal victory ^{[1] [5]}. Procedural dismissals and settlements can be functionally advantageous: they avoid trial exposure and create public perceptions of vindication, but they do not uniformly equate to definitive judicial findings on the underlying merits of disputed conduct ^{[1] [5]}.

2. What the dossier counts as losses — major rulings that carry large penalties

Contrastingly, the provided material documents significant legal defeats for Trump, including a New York civil fraud ruling ordering nearly $355 million in penalties and a ban on operating his New York business, and a criminal conviction on 34 counts of falsifying business records tied to hush-money payments ^{[3] [4]}. These items represent substantive judicial determinations rather than procedural outcomes or settlements: they reflect judges or juries rendering adverse decisions on the merits with concrete sanctions and, in the criminal instance, felony convictions ^{[3] [4]}. The dossier frames these as major losses that materially alter legal and financial exposure.

3. Timing matters: mixing 2025 reports with later January 2026 items

The sources cover a span of publication dates. Most early items pertain to developments in September–October 2025 about lawsuits being dismissed, refiled, or settled ^{[1] [2] [5]}. Two pieces in the dossier carry publication dates of January 1, 2026 and report the civil fraud penalty and the criminal guilty verdict ^{[3] [4]}. The inclusion of these January 2026 items means the dossier aggregates pre- and post-election-period litigation and outcomes; readers should note that some entries report developments after October 23, 2025 and thus reflect later adjudications or reporting ^{[3] [4]}.

4. How different sources frame the same events — agendas and emphasis

The dossier’s sources vary in emphasis: some highlight procedural setbacks for defendants (dismissals, refilings) and settlements that underscore vindication narratives, while others spotlight punitive judgments and criminal findings as conclusive losses ^{[2] [3] [4]}. Each framing can serve different agendas: emphasizing settlements and dismissals tends to portray legal risk as managed or overstated, while emphasizing penalties and convictions foregrounds accountability and systemic consequence. Treating all sources as biased, the dossier’s juxtaposition reveals a contested public narrative in which both victory and defeat elements are selectively emphasized ^{[1] [4]}.

5. What’s missing from the dossier — the impossible task of counting ‘wins’ and ‘losses’

The materials do not provide a systematic tabulation of every lawsuit Trump has filed or faced across decades, nor a consistent methodology for what counts as a “win” or “loss.” Lawsuits can end via settlement, dismissal, vacatur, injunction, judgment, plea, conviction, or acquittal, and parties often appeal or negotiate, altering the final status. The dossier’s snapshots cannot substitute for a comprehensive, verified ledger; therefore, any simple numeric claim about total wins or losses would be incomplete and potentially misleading given the multiplicity of civil and criminal matters over decades ^{[1] [2] [3]}.

6. Reconciling competing facts — what can be stated with confidence now

From the supplied documents, it is verifiable that Trump achieved high-value media settlements and secured at least some dismissals in 2025, and that later items report a New York civil penalty of roughly $355 million and a criminal guilty verdict on business-records counts reported January 1, 2026 ^{[1] [5] [2] [3] [4]}. These are concrete, reported outcomes in the dossier: settlements and dismissals are documented alongside large civil penalties and criminal convictions. The exact total number of lawsuits won or lost across his lifetime is not enumerated by the supplied materials and therefore cannot be definitively tallied from this dossier alone ^{[1] [3]}.

7. Bottom line for readers seeking a single number

The dossier demonstrates that any accurate answer requires a clear definition of “won” versus “lost,” comprehensive case listing, and final-case dispositions including appeals. Absent that exhaustive accounting in the provided documents, the only defensible conclusion is that Trump’s litigation record includes both significant victories (settlements/dismissals) and significant defeats (large civil penalties and criminal convictions as reported), but the dossier does not provide a authoritative count of total lawsuits won or lost in his lifetime ^{[1] [3] [4]}.