The courtroom action this week represents a potential reversal of fortune for Trump following a long list of defeats the President has tasted on cases from immigration to the 2020 census to his efforts to thwart Democratic oversight to his central campaign promise to build a border wall. For a man who bills himself as one of life’s ultimate winners, Trump’s legal losing record is a branding nightmare.
While the law has often frustrated Trump’s political goals, he has still used it as a weapon to combat Democrats, as the glue in his conservative coalition and to postpone threatening political crises.
Often — as in the case of Trump’s national emergency declaration designed to fund his border wall or the census — it seems as if the long odds in court do not deter the President. The law gives Trump another venue for the endless fights that sustain his politics and his personality. Even if he loses he is showing his supporters he’s never giving up the battle.
Trump’s judicial appointments are likely to shape the character of American life for years after he’s left the White House. And it’s still possible court rulings could pose an existential threat to his personal and business legacy given the flurry of cases currently open in New York.
A rare win
As is often the case, Trump’s wins in the courts have been outnumbered by his losses this week.
Yet Trump’s relationship with the courts is actually far more complicated than the win-loss ratio with which he judges his own success and that of everyone around him.
He used lawsuits to save face, to offer a new venue to prolong a fight, to put off a reckoning or agreed out-of-court settlements to limit the costs of personal and business liabilities.
Legal power plays
As President, Trump has also used courts to fulfill wider goals than simply winning and losing cases, especially since he’s struggled to get many major bills through Congress — apart from a big tax reform program.
With bold assertions of executive power, Trump has made the courts a constant presence in his presidency.
When he’s won, he’s trumpeted it. When — more often — he loses, the judgments become exhibits in his foundational political case that an elite establishment is out to get him and that he’s being treated unfairly.
Administrations often try to achieve through the courts what they cannot legislatively — and the Trump team along with allied GOP states has been especially enthusiastic in this regard.
The case also reflects the manner in which, in an era of congressional stasis and polarization, courts are being called upon to do the job lawmakers might once have done.
Judge Kurt Engelhardt questioned why, after a US district judge declared the whole ACA unconstitutional, Congress did not pass a law clarifying what provisions should stay on the books.
“Why does Congress want the … judiciary to become the taxidermist for every legislative big-game accomplishment that Congress achieves?” Engelhardt asked.
The administration’s legal gambits have often reflected the chaos and politicized arguments that rock the administration every day and have sometimes hampered its own chances of success.
Sometimes, Trump has turned to personal litigation to try to frustrate his political enemies.
The President has sometimes been the target of litigation as well: Democrats are increasingly turning to the courts to enforce subpoenas.
The cases could eventually lead to profound rulings about the scope of presidential power that could resonate for decades to come. And if Trump were to refuse to hand over documents or tax returns ordered by the courts, he could turn overused predictions of a looming constitutional crisis into reality.
That’s an example of where legal action suits Trump just fine.
In such cases there’s a good chance he will fail on the merits — but the law’s slow march means that he’s at least putting off a threatening political situation for another day — possibly even beyond the 2020 election.
Each new challenge becomes a new example of the “presidential harassment” — the term Trump and his allies use to stoke a sense of victimhood around his administration and to solidify his support with his all-important political base.
A lasting legal legacy
The political synergy between Trump and the courts has an even deeper connection to his presidency than cases in which he is embroiled.
The President’s decision to publicize a list of potential Supreme Court justices vetted by the Federalist Society was in retrospect one of the smartest moves of his 2016 campaign, embedding evangelical and judicial conservatives into his support base despite doubts about his character and ideology.
Trump has delivered on his vows to build a conservative majority on the Supreme Court with the seating of Justices Neil Gorsuch and Brett Kavanaugh. The court’s new ideological balance means that rulings favorable to Trump’s leanings on everything from deregulation to abortion could be handed down for years to come.
And the President’s alliance with Senate Republican Majority leader Mitch McConnell has been confirming conservative judges to lower courts at an impressive clip.
There is no guarantee that such judges will necessarily share Trump’s challenging and unique interpretations on the limits of presidential power.
But some of them could provide a more ideologically friendly judiciary for Trump’s policy efforts if he wins a second term and could help break his losing streak.
And the Trump class of judges at all levels of the federal bench is likely to frustrate a future Democratic president.
CNN’s Dan Berman contributed to this report.