Background
Donald Trump has a history of legal actions against media outlets, with varying degrees of success. At the same time, other high profile defamation cases, such as Dominion's lawsuit against Dominion have broke new ground for huge defamation judgments. Recently, ABC News settled a defamation lawsuit with Trump for $15 million over incorrect statements made by an ABC anchor regarding the E. Jean Carroll case. This settlement represents one of Trump's most significant victories against media outlets.
Some background on the cases mentioned in the initial answers: https://www.reuters.com/world/us/donald-trumps-lawsuits-against-media-companies-2024-12-20/
Resolution Criteria
A lawsuit will be considered "successful", leading to a YES resolution, if it results in either:
A court judgment in Trump's favor of $1 million or more (after all appeals exhausted).
A settlement of $1 million or more in Trump's favor
Attorney fee awards will not count towards the $1million. Agreed payments to Trump-related third party organizations such as campaign funds or the Trump Presidential Library will count.
Markets will resolve NO if:
The lawsuit is dismissed with prejudice or summary judgment is given against Trump's side (after all appeals exhausted)
For cases that are appealed, the final resolution after all appeals will determine the outcome. If a case is brought in state court and successfully removed to federal court this will count as the same case continuing. If answers are added that are duplicative or not in the spirit of the question I will resolve them as N/A. I will extend the closing date if cases are ongoing.
Considerations
Defamation cases against media outlets typically face high legal barriers in the U.S. due to First Amendment protections and the need to prove actual malice for public figures
The ABC News settlement represents an unusual outcome compared to historical patterns, as most of Trump's previous lawsuits against media outlets have been unsuccessful.
The success of the Dominion lawsuit against Fox News ($787.5 million settlement) has created new precedent for large media defamation settlements, though under different circumstances
The Des Moines Register lawsuit is currently active, with the newspaper standing by their polling methodology and reporting
Media companies and their parent corporations may choose to settle lawsuits in order to maintain positive relationships with the Trump administration