Trump, the Courts, and the Conservative Machine
“To successfully wage [a judicial] campaign, you need three things: money, legal personnel and a judiciary that’s receptive to strategically selected and timed legal arguments.” These words, spoken by attorney Damien Schiff at a Federalist Society legal forum, outline the strategy that conservative legal groups have increasingly relied on in their judicial advocacy. Schiff’s group, Pacific Legal Foundation, is one of many conservative legal advocacy groups that receive funding from petrochemical billionaire, Charles Koch.
Thanks to donors like Koch, money is never going to be an issue for groups such as Schiff’s, and, since Donald Trump’s first presidency, these groups have easily been able to find the receptive judiciaries they need. This is a result of the increasing polarization of the judicial branch, enabled by the advocacy of legal groups such as the Federalist Society, which have doggedly promoted conservative, originalist judges since the decision of Roe v. Wade in 1973. Looking ahead at the next four years, it is incredibly likely that President Trump will continue the process he began in his first term, filling the federal judiciary, and particularly the Supreme Court, with more and more conservative judges and justices. This has the potential to weaken the legitimacy of the federal judiciary for decades to come.
Reflecting on the First Trump Presidency
During Donald Trump’s first campaign for president in 2016, he won support from social conservatives in part by agreeing to fill Supreme Court vacancies from a list of prospective nominees put forward by the Federalist Society, a prominent conservative legal organization. Indeed, exit polls from the 2016 election suggest that court-focused voters played a noteworthy role in Trump’s narrow victory. Throughout Trump’s four years in office, he drew on Federalist Society rosters to appoint hundreds of federal judges. These included 174 district court judges, 54 appeals court judges and, of course, three Supreme Court justices, all but eight of whom had ties to the Federalist Society. Notably, many of these appointees had previously been openly engaged in Republican causes, with approximately 75% of the appointees having previously donated to political offices, a higher figure than among Obama or Bush nominees.
These efforts to fill the federal judiciary with conservative judges were largely spear-headed by a few prominent individuals. Leonard Leo, chairman of the Federalist Society, advanced many of Trump’s judicial nominees, while Donald McGahn, former White House counsel, vetted those nominees. Finally, Mitch McConnell, then Senate majority leader, played a crucial role in pushing those nominees through confirmation after blocking the confirmation of over one hundred of former President Obama’s nominees. McConnell accomplished this by both prioritizing judicial nominees above all else and by eliminating many of the same Senate rules that he had once leveraged to block Obama’s nominations. President Trump’s Supreme Court nominations were also supported financially by conservative lobbyists. The Judicial Crisis Network, a dark money group run by Leonard Leo’s allies, spent millions on media campaigns supporting the confirmation of these nominees. In turn, the group, which is now known as the Concord Fund, received much of its funding from the Wellspring Committee, a group founded by Charles and David Koch.
President Trump’s judicial nominees have played a significant role in shifting the courts to the right and leading to major conservative victories. Notably, these include Dobbs v. Jackson Women’s Health Organization, which stripped federal protections for the right to abortion, and Loper Bright v. Raimondo, which limited the authority of federal agencies to interpret the law. The impact of Trump’s nominees has remained significant despite the many judicial nominees confirmed during the Biden presidency. Although President Biden actually appointed more judges in total than President Trump, the vast majority of his nominations were on the district court level, leaving the appellate courts overwhelming conservative. In particular, President Trump flipped the ideological balance of three circuit courts and significantly narrowed the margins of several more. Although President Biden did flip the Second Circuit back, the margins of traditionally liberal circuits remain much narrower than they were prior to 2017, which will potentially make it difficult for liberal organizations to successfully challenge policies in the second Trump administration.
Conservative Lobbyists in the Federal Judiciary
Beyond advocating for President Trump’s judicial nominees, conservative lobbyists have also played a significant role in funding impact litigation for conservative causes. Nowhere is this clearer than in Loper Bright v. Raimondo, which stripped regulatory agencies of much of their power. The lawyers representing the plaintiffs in this case belonged to Cause of Action, a law firm disclosing no donors, but with ties to Americans for Prosperity, another group funded by Charles Koch, a long-time champion of anti-regulatory advocacy. Meanwhile, Cause of Action’s founder, Daniel Epstein, was previously an associate at the Koch Foundation, further solidifying the connection between Charles Koch and Loper Bright. Though this is but one case of many, it reflects a broader pattern of conservative lobbyists funding impact litigation, primarily through dark money organizations.
The increasing influence of dark money organizations in the federal judiciary, many of which have ties to Leonard Leo and Charles Koch, limits the transparency around high profile cases such as Loper Bright. These dark money groups, due to their status as 501(c)(4) or 501(c)(6) non-profits under the U.S. tax code, are not required to publicly disclose their donors. Though it is possible, in rare instances, to identify individual donors through careful examination of the donor’s tax records, the lack of transparency within these organizations makes it virtually impossible for the public to be aware of all the major stakeholders influencing high-profile cases. This enables situations, such as those surrounding Loper Bright, in which billionaire lobbyists are able to work behind the scenes to put their thumb on the scale towards whatever outcome advances their own private profits.
Breaking with the Federalist Society?
Although President Trump’s first term judicial picks were almost universally promoted by the Federalist Society, it appears that Trump has since broken with many of these former allies. This break was largely the result of Trump’s growing frustrations with judicial nominees that he perceived as too independent and “weak,” particularly those who opposed his attempts to overturn the 2020 election. This perceived weakness was likely a result of judges’ unwillingness to side with Trump on issues that went against the so-called “elite opinion.” A clear indication of this break is the deteriorating relationship between Trump and Leonard Leo, who supposedly haven’t spoken since 2020, after Leo repeatedly ignored Trump’s calls enlisting legal aid regarding the 2020 election. That said, Leo himself has theorized that Trump will likely continue nominating the conservative, originalist judges he supports, because the Federalist Society has already “won the philosophical debate.”
Moreover, despite the recent conflict between President Trump and the Federalist Society, Leonard Leo has continued to funnel money into the conservative cause by donating to Project 2025. For example, both the 85 Fund and the Concord Fund, run by close allies of Leo, have donated millions of dollars to many of the groups involved with Project 2025, including the Heritage Foundation. Though Trump himself has repeatedly disavowed Project 2025, he has since appointed several of its authors to key positions in the administration, indicating that there are still financial ties between his administration and Leonard Leo, albeit less directly than in his previous term.
Predictions for Trump’s Second Term
Considering President Trump’s splintering relationship with the conservative legal establishment and increasing frustration with the courts, it seems likely that there will be a greater degree of volatility in Trump’s handling of judicial issues moving forward. For example, while Trump went into the 2016 election with a comprehensive list of prospective nominees, he has yet to offer a similar list for his second term. Though there has been significant speculation about individuals who may be on a short-list for judicial nominees, it is also possible that Trump might name individuals who aren’t on any obvious short-lists. As Steven Calabresi, Federalist Society co-founder, has said, “Sometimes I think what Trump wants most is to stick his thumb into the eyes of his opponents.”
The one thing that is clear about Trump’s second term nominees is that loyalty will likely play a heavy role in any nomination. Mark Paoletta, the general counsel of the Office of Management and Budget, has said that Trump is looking for appointees who are “truly committed to helping him accomplish his agenda,” commenting that too many people in Trump’s first term “actually disagreed with the president and tried to thwart him.” For example, one of Trump’s allies, Mike Davis, founder of the Article III Project, has cited U.S. District Judge Aileen Cannon as potentially due for a promotion. Cannon, most notably, is the judge who dismissed the classified documents case on tenuous legal grounds.
Though it remains unclear who Trump might nominate, several of his close allies have been building new recruiting pipelines, separate from the Federalist Society, to reduce the chances that political appointees might frustrate a more radical second term agenda. Two of Trump’s allies who might be involved in these efforts are Stephen Miller, who serves as deputy chief of policy in the new administration, and John McEntee, a trusted aide from Trump’s first term. Miller, in particular, is the founder of the America First Legal Foundation, an organization focused on recruiting a new generation of “America First” lawyers, similar to Mike Davis’ Article III project. McEntee, meanwhile, who was tasked in 2020 with ridding the Trump administration of disloyal appointees, has since worked with Project 2025 to search for potential second term Trump lawyers and judges. Similarly, another prominent legal organization and member of the Project 2025 advisory board, the First Liberty Institute, has worked since 2016 to compile judicial opinions and writings, which may inform how a potential Supreme Court nominee would rule.
Regardless of who plays a role in advancing prospective nominees, moving into the second term with a Republican-controlled Senate and Judiciary Committee will enable Trump to make a lasting impact on the federal judiciary for decades to come. It’s expected that over 100 seats will likely open up in lower courts throughout Trump’s second term. Most notably, conservatives are hoping for future Supreme Court retirements, looking particularly at Justices Alito and Thomas, which would make Trump the first president since Franklin D. Roosevelt to appoint a majority of the court’s justices.
The scope of Trump’s impacts on the judiciary will, however, be limited by the number of court vacancies, which will likely be far less than during his first term or the Biden presidency. Currently, there are only 40 vacancies, with 20 more expected in the near future. Another 247 judges — 131 Democrat-appointed and 116 Republican-appointed — will be eligible to move into semi-retirement over the next term, opening further vacancies. That said, this kind of retirement is not required, and research has shown that judges are increasingly timing their retirement to presidencies of the same political party. Even with fewer vacancies, however, Trump will presumably be able to secure long-term conservative majorities on some courts and may flip others. These nominees will likely be considerably more extreme than in his first term, even in Democratic states, as Senate rules no longer require the consent of home-state senators for appellate-level judicial appointees.
Though it is difficult to predict who Trump might appoint to the Supreme Court, in the likely event that Justices Thomas and Alito choose to retire, some judges who might be due for promotion are Matthew Kacsmaryk, Kathryn Mizelle, and James Ho. U.S. District Judge Matthew Kacsmaryk is a Trump appointee and former deputy counsel for the First Liberty Institute, most known for reinstating the Trump “Remain in Mexico” policy and suspending FDA approval of the abortion pill Mifepristone. Meanwhile, U.S. District Judge Kathryn Mizelle, another Trump appointee, is most known for her ruling striking down President Biden’s federal mask mandate on public transportation.
Finally, and perhaps most likely to see a promotion, Fifth Circuit Judge James Ho, has a long history of conservative rulings which may appeal to President Trump. For example, in his concurring opinion in United States v. Abbott, he described illegal immigration as an “invasion.” Additionally, he ruled in favor of Kacsmaryk’s suspension of mifepristone approval, citing the “aesthetic injury” doctors experience during abortions, a rationale that even the highly conservative Supreme Court decisively rejected.
Regardless of whether any of these individual judges are nominated for the Supreme Court, the mere fact such controversial figures are even being considered as options is a clear indicator of just how polarized judicial nominations have become.
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