One of the things that has become clear about Donald Trump is that he is obsessed with winning. During the 2016 campaign, he regularly went off on a riff like this:

Trump actually suggested that he would be winning so much that his supporters would get tired of winning. But according to the Washington Post’s Fred Barbash and Deanna Paul, he is actually on a historic losing streak with the courts.
Federal judges have ruled against the Trump administration at least 63 times over the past two years, an extraordinary record of legal defeat that has stymied large parts of the president’s agenda on the environment, immigration and other matters…
Two-thirds of the cases accuse the Trump administration of violating the Administrative Procedure Act (APA), a nearly 73-year-old law that forms the primary bulwark against arbitrary rule. The normal “win rate” for the government in such cases is about 70 percent, according to analysts and studies. But as of mid-January, a database maintained by the Institute for Policy Integrity at the New York University School of Law shows Trump’s win rate at about 6 percent.
On almost every major initiative other than tax cuts for the wealthy, this president hasn’t been able to work with Congress to pass legislation. So instead, he has issued executive orders and attempted to roll back regulations. All of those have been met with court challenges, and the administration is losing most of those battles.
Contrary to what Trump would have you believe, that losing streak is not simply the result of “liberal judges.”
Democratic appointees, many of them tapped by presidents Barack Obama and Bill Clinton, are responsible for 45 decisions. Republican appointees dating back to President Ronald Reagan issued the other rulings. Magistrate judges, who are not appointed by presidents, made three of the decisions.
On major issues on which multiple judges have ruled, there has been little disagreement among them, no matter where the judges are located or who appointed them.
As the quote above indicates, this administration’s losing streak is primarily a result of their failure to follow the Administrative Procedures Act (APA)
The Administrative Procedure Act, sometimes called the “Magna Carta of administrative law,” is a 1946 statute that governs hundreds of federal agencies…It requires that agencies go through a process known as “notice and comment” before issuing, amending or repealing “substantive rules.” As part of that process, the agency must publish proposed actions in the Federal Register and then give the public at least 30 days to submit feedback. When it finalizes its proposal, the agency must respond to issues raised by the public comments and must explain why it settled upon the course of action that it chose. The explanation must show why the agency’s action is reasonable and not “arbitrary” or “capricious.”
As many people predicted early on with this administration’s attempts to roll back environmental regulations, these court losses have particularly hampered their efforts in that arena. So while there has been a lot of chatter about Trump rolling back Obama’s Clean Power Plan and new auto emission standards, nothing has actually changed, because those efforts have been tied up in the courts.
To get some idea of how adherence to APA will continue to prove problematic for the administration in rolling back environmental regulations, it is important to keep the historical record in mind. Back in 1963, the Clean Air Act was signed into law, establishing the role of the federal government in regulating contributions to air pollution. The 2007 Supreme Court decision in Massachusetts vs EPA affirmed that greenhouse gasses are air pollutants and allowed states to sue the EPA for failure to adequately regulate them. Based on solid scientific evidence, the Obama administration announced the Endangerment Finding in 2009, which declared that “carbon dioxide and other greenhouse gases constitute a threat to human health and welfare,” allowing the EPA to regulate those emissions. The Endangerment Finding was the basis for both the Clean Power Plan and higher auto emission standards. Since that finding was announced, the scientific evidence for it has grown stronger.
In order to follow the requirements of APA in their efforts to roll back environmental regulations, the Trump administration would have to not only open their intentions to public comment, they would have to address the issues raised and demonstrate to the court that their actions are not “arbitrary” or “capricious.” In other words, they would have to take the historical record of congressional actions and court rulings into account and ground their actions in scientific fact, which will be difficult, if not impossible, to do.
One of the metrics often applied to Trump and his administration is to evaluate the extent to which their actions spring from malevolence or incompetence. More often than not, it is a combination of the two. When applied to their performance in the courts, the original intent of the policy under consideration might be grounded in malevolence, but their losing streak is clearly a result of incompetence.