From friends to foes: how Trump turned on the Federalist Society
The word was 'sleazebag', which Trump deployed as part of a lengthy broadside on Truth Social, his social media platform. The targets of his wrath were the Federalist Society, an influential conservative legal organization, and Leonard Leo, a lawyer associated with the group who has, in recent years, branched out to become one of the most powerful rightwing kingmakers in the US.
In his post, Trump said that during his first term 'it was suggested that I use The Federalist Society as a recommending source on Judges. I did so, openly and freely, but then realized that they were under the thumb of a real 'sleazebag' named Leonard Leo, a bad person who, in his own way, probably hates America, and obviously has his own separate ambitions. He openly brags how he controls Judges, and even Justices of the United States Supreme Court – I hope that is not so, and don't believe it is!'
Founded in 1982, the Federalist Society is an important player in the conservative movement. Many conservative lawyers, judges, law students and law clerks are members of the group, attend its events or run in its general orbit. Republican presidents use its recommendations to pick judges for vacant judicial seats.
In the days following Trump's Truth Social harangue, people in the conservative legal world, which is centered in Washington DC but spans law schools and judge's chambers across the country, are wondering what this rift portends. Is this a classic Trump tantrum that will soon blow over? Or does it speak to a larger schism, with even the famously conservative Federalist Society not rightwing enough – or fanatically loyal enough – to satisfy Trump?
'I don't think this will blow over,' Stuart Gerson, a conservative attorney and a former acting US attorney general, said. 'Because it's not an event. It's a condition … He thinks judges are his judges, and they're there to support his policies, rather than the oath that they take [to the constitution].'
In recent months, Trump has been stymied repeatedly by court rulings by federal judges. His rage has been particularly acute when the judges are ones whom he or other Republican presidents appointed. The Maga world has turned aggressively against Amy Coney Barrett, for example, after the supreme court justice voted contrary to the Trump line in several key cases.
The immediate cause of Trump's recent outburst was a ruling by the US court of international trade against his sweeping tariffs on foreign goods. In this case, his anger appears to have had less to do with the judges than with the fact that a group of conservative lawyers and academics, including one who co-chairs the board of the Federalist Society, had filed a brief in the case challenging his tariffs.
Trump is probably also aware that the New Civil Liberties Alliance (NCLA), an anti-regulation, pro-free market legal group affiliated with Leo and the billionaire Charles Koch, has sued, separately, to stop the tariffs.
John Vecchione, an attorney at the NCLA, noted that the Federalist Society is a broad tent, with conservative jurists of many different inclinations and factions, including free marketeers and libertarians who do not subscribe to Trump's economic nationalism. Members often disagree with each other or find themselves on different sides of a case. This February, a federal prosecutor affiliated with the group, Danielle Sassoon, resigned after she said the Trump administration tried to pressure her to drop a case.
The 'real question', Vecchione said, is what diehard Maga lawyers closest to Trump are telling him.
'Are they trying to form a new organization? Or are they trying to do to the Federalist Society what they've done to the House Republican caucus, for instance … where nobody wants to go up against Trump on anything?' he said. 'I think that some of the people around Trump believe that any right-coded organization has to do his bidding.'
A newer legal organization, the Article III Project (A3P), appears to have captured Trump's ear in his second term. The organization was founded by Mike Davis, a rabidly pro-Trump lawyer, and seems to be positioning itself as a Maga alternative to the Federalist Society. On its website, A3P claims to have 'helped confirm' three supreme court justices, 55 federal circuit judges and 13 federal appellate judges.
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Davis recently asserted in the Hill that the Federalist Society 'abandoned' Trump during his various recent legal travails. 'And not only did they abandon him – they had several [Federalist Society] leaders who participated in the lawfare and threw gas on the fire,' Davis said.
Although Leo was a 'a close ally' of Trump during his first term, the Wall Street Journal reported, Trump and Leo 'haven't spoken in five years'.
Leo has responded to Trump's outburst delicately. In a short statement, he said he was 'very grateful for President Trump transforming the federal courts, and it was a privilege being involved', adding that the reshaping of the federal bench would be 'President Trump's most important legacy'.
Yet this Tuesday, a lengthy piece in the Wall Street Journal – pointedly titled 'This Conservative Is Doing Just Fine, Thank You, After Getting Dumped by Trump' – argued that Leo is 'unbounded by the pressures of re-election or dependence on outside money', and is the 'rare conservative, who, after being cast out of Trump's inner circle, remains free to pursue his own vision of what will make America great again'. In 2021, a Chicago billionaire gave Leo a $1.6bn political donation, thought to be the largest such donation in US history. As a result, Leo has an almost unprecedented power in terms of dark-money influence.
The article also noted that much of Leo's focus has shifted to the entertainment industry, where he is funding big-budget television series and films that channel conservative values.
Vecchione thinks that Trump's tendency to surround himself with sycophants and loyalists will work against him.
'If you have a lawyer who only tells you what makes you happy, and only does what you say to do, you don't have a good lawyer,' Vecchione said. 'That's not a good way to get lawyers. Not a good way to get judges, either.'
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