The familiar maxim “If at first you don’t succeed, try, try again” that we pass along to our children encourages resilience and perseverance in the face of failure. We have reason to think someone encouraged former President Donald Trump to take the expression to heart, and, unfortunately, he did.
There are few truisms in life, but here’s one: Trump is litigious. Very litigious.
The many lawsuits Trump and his allies filed in 2021, the vast majority of which he lost, provide a case study in perseverance. Trump persevered despite the fact that doing so was often irrational and immoral.
There are few truisms in life, but here’s one: Trump is litigious. Very litigious. Before the 2016 election, a USA Today analysis found that he and his businesses had been involved in 4,095 lawsuits over three decades, and in more than 2,100 of those suits as the plaintiff.
Lawsuits, even ones that are destined to fail, can still lead to success. Filing a lawsuit can scare people; lawsuits are often costly and time-consuming to defend against. Filing a lawsuit can also lead to beneficial delays, like, to take two wild hypotheticals, delaying a state investigation into potentially fraudulent behavior or a congressional investigation into an insurrection.
Let’s begin with the lawsuits related to the 2020 election, some of which commenced before 2021. Quick reminder: Joe Biden won the election. As a direct and entirely predictable result of winning a presidential election, Biden is now the president of the United States. Also, you can search and search for massive voter fraud that led to Biden’s win, but it will be less fruitful than searching for a snow leopard in a blizzard, and you will come up empty. The only significant fraud perpetrated in the 2020 presidential election is the lie that there was fraud.
It should therefore come as no surprise that lawsuits filed by Trump and his allies claiming there was fraud in the 2020 election failed. “Failed” might be too tepid a word to describe the fate of these election-related lawsuits: These suits belly-flopped into a pool containing nothing but air and concrete. By one estimate, Trump and his allies have a win-loss record of 0-40 when it comes to post-election lawsuits.
Let’s continue our tour of Trump’s lawsuits by moving on to something that happened right after the election: the insurrection and the effort to stop the election certification. A House select committee is investigating the events of Jan. 6 to determine who knew what and when. In more predictable news, the man who led our government then and apparently tried to subvert the peaceful transfer of power from himself to Biden doesn’t want Congress looking under the hood to find out exactly what happened before and on Jan. 6. Trump sued to prevent the committee from obtaining certain White House documents related to the insurrection. He lost in trial court and again in appeals court. Never one to be deterred by the law or facts, Trump has appealed to the Supreme Court for emergency relief. Stay tuned to see what our nation’s highest court does.
Trump’s only problem with his suit against James is that the law is against him.
And just when we thought the year might end before another big Trump suit hit, the former president sued New York Attorney General Letitia James. Her office is investigating whether the Trump Organization may be civilly liable for, among other things, inflating property values to obtain loans and deflating property values to get beneficial tax treatment. James’ office is also working with the Manhattan District Attorney’s Office on a criminal investigation into similar alleged behavior. (Trump has not been accused of wrongdoing in the investigations.)
Trump’s argument is that James’ investigation is politically motivated and she must restrict it or halt it. If your bingo card had Trump calling James’ inquiry a “political witch hunt,” then place a marker on that square. It is worth noting that Trump’s suit arrived on the courthouse doorstep shortly after James’ office subpoenaed Trump for testimony. As is often the case with his lawsuits, Trump’s only problem with his suit against James is that the law is against him. Prosecutors can have political biases without violating the constitutional rights of the people the prosecutor is investigating. That prosecutor simply must set them aside while doing her job. This is but a tour of some of the highlights (or lowlights) of the cases Trump, and his allies, filed in 2021. If we endeavored to provide an exhaustive list, it would almost certainly be out of date before it was finished, as Trump would likely have filed another suit by then. So, kids, aim high, try hard and persevere. But if you’re thinking of filing a lawsuit, check to see if you have a legally recognizable claim. With that, let’s say goodbye to 2021 and the many hours Trump’s lawyers have billed on his behalf.
Jessica Levinson is a Loyola Law School professor and MS NOW columnist. 
