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Here Are the Connections Between the People Behind Trump’s Prosecutions

The prosecutions of President Donald Trump seem resistant to interpretation because of their strange combinations of intricacy, sordidness, and impact. The cases are filled with details that overwhelm and repel: affairs, thefts, hush money payments, cardboard boxes near toilets, the alleged complicity of property managers and valets. At the same time, their political effects are enormous, even overwhelming. Taken as a whole, the cases discourage sustained engagement, which may explain why many Americans have seemed disassociated from them, despite the drumbeat coming from both established and insurgent media.

In this context of disengagement, it is all the more telling that each of these cases are compromised in at least one significant way. Nobody at the Justice Department, which was providing federal funds to the Fulton County, Georgia District Attorney’s office, was aware of a romantic relationship between District Attorney Fani Willis and Nathan Wade, whom Willis appointed as one of the special prosecutors on the case despite Wade’s lack of experience prosecuting complex criminal cases. The crime that Trump was charged with in the New York case was a misdemeanor that District Attorney Alvin Bragg upgraded to a felony—an unusual move. The cardboard boxes with classified documents in Trump’s Mar-a-Lago bathroom, which are being investigated by Justice Department special counsel Jack Smith, seem to differ from the cardboard boxes with classified documents in President Biden’s Delaware garage only based on loose interpretations of Trump’s intent. 

This disjuncture between the cases’ strangeness and their weakness may not be a coincidence. In fact, the strangeness may function to mask a more familiar Washington story: a group of interconnected partisans hounding a president and corrupting American law. 

There is no smoking gun that proves this—if a smoking gun even exists in a city as reliant on unattributable nods, headshakes, and hints over phone calls as Washington, D.C. But links between movers in the four prosecutions indicate political and financial incentives, as well as loyalties and patronages, that could motivate a play against a populist presidential candidate on behalf of insider Washington. So do some of these players’ links to a past history that maps, unsettlingly, onto current events, suggesting that the prosecution against Trump is the most obvious symptom of longer-term distortions of the American justice system. 

The most accessible point of entry into this interconnected network may be last Thursday’s press conference held by Alvin Bragg—specifically, Matthew Colangelo, the man standing behind Bragg a few paces to his right. In December 2022, less than a month after Trump announced his reelection bid, Colangelo departed the Justice Department to “help lead” Bragg’s inquiry. Colangelo does not leave much of a paper trail, but his career is an emblem of professional-political advancement through narrow, powerful corridors.  

A graduate of Harvard College and Law School, he clerked on the Second Circuit Court of Appeals for then-Judge Sonia Sotomayor. He then served at the NAACP Legal Defense & Educational Fund, and as Deputy Assistant Attorney General for Civil Rights at the U.S. Department of Justice in the Obama Administration. During the Trump Administration, he worked for the New York Attorney General’s office investigating President Trump’s businesses alongside future District Attorney Bragg, then returned to the Justice Department after President Biden’s election as acting associate attorney general, the third highest position there. At the point when he left the Justice Department in 2022, he was serving under Associate Attorney General Vanita Gupta: formerly of the NAACP Legal Defense Fund and linked to the Open Society Foundations, whose funder, George Soros, helped fund District Attorney Bragg’s election in 2021, and whose current leader, Alex Soros, has “amplified” Bragg’s recent verdict.

Colangelo’s wife, Anne Small, charted an intersecting trajectory. She attended Yale and Harvard Law and served as editor of the Harvard Law Review, then clerked for 2nd Circuit Court of Appeals Judge Guido Calabresi, Sotomayor’s teacher, and later for Supreme Court Justice Stephen Breyer. She worked for several years at the Washington law firm WilmerHale, the operating base of former Clinton administration’s Deputy Attorney General Jamie Gorelick, a Harvard classmate of Attorney General Garland’s who was probably most responsible for that official’s career trajectory. 

During the Obama administration, Small went to work for the SEC and for the White House Counsel’s office. There, and earlier at WilmerHale, she overlapped with Ed Siskel, the current White House counsel who heads an office which, according to Nathan Wade’s expense reports and billing records, met with Wade twice during his investigations. After Trump’s election, Small began serving on the board of directors of her husband’s former employer, the NAACP Legal Defense Fund, alongside Jonathan Soros of the Soros family, a major NAACP Legal Defense Fund donor. She also took on employment at the New York hedge fund Renaissance Technologies, founded by the billionaire and high-dollar Democratic donor Jim Simons.

Jack T. Smith, the federal prosecutor whom Attorney General Garland appointed in 2022 to oversee two federal investigations into Trump despite a trail of questionable cases, is also linked to this world. A graduate of SUNY Oneonta and then Harvard Law who is a registered independent, he entered the spheres of liberal and legal royalty via his wife Katy Chevigny, a documentarian who recently produced the Netflix special “Becoming” about First Lady Michelle Obama. Chevigny is the daughter of the late, eminent New York University School of Law professor Paul Chevigny, who had links to the Open Society Foundations and its beneficiary, the Brennan Center for Justice—the leftist legal advocacy group funding the daughter of the presiding judge at Trump’s trial in New York. 

Outside of these immediate connections, there are other instructive ones between Washington movers and the cases at play. Among them is Norman Eisen, a former Harvard Law School classmate of and special counsel to Obama. The New York Times quoted Eisen in January justifying the White House Counsel’s office’s meetings with Nathan Wade by saying that “it was common for the…Counsel’s Office to become involved when the testimony of officials from former administrations is sought, because there may be issues of executive privilege.” 

This may or may not be the case. But unmentioned by the Times, even as it was known around Washington and New York, was the fact that, while Eisen ran cover in the paper for Ed Siskel and Nathan Wade, he was convening weekly meetings to strategize on the prosecutions against Trump.

These weekly meetings convened by Eisen have included briefings by government officials and are filled with people who have spent thirty years making their influence felt in Washington. Laurence Tribe, whose career at Harvard intersected with Small’s authority-interactive stint as the Harvard Law Review editor, argued Bush v. Gore before the Supreme Court in 2000. William Kristol, the former editor of the Weekly Standard and seeder of the Iraq invasion and Sarah Palin’s vice presidential nomination, is running a 501(c)(4) pushing Republican legislators to fund the proxy war in Ukraine. Jeffrey Toobin and George Conway have been major legal-media operators since the 1990s.  

Many of these players and their allies also have experience with an earlier, era-defining political event also involving affairs, backstabbing, celebrity-chasing, unreliable witnesses, unprecedented politics, solemn coverage, and a weak underlying legal case: the prosecution of William Jefferson Clinton in 1998. 

Though this fact is largely forgotten outside of Washington, D.C., it was William Kristol and George Conway who brought what we know as the Lewinsky scandal to public notice 26 years ago this past January. At that point, Conway, a Yale Law graduate, was a partner at the corporate law firm Wachtell Lipton, which had gained influence in Washington thanks to the raft of corporate mergers spurred by government deregulation the decade before. Outside of law, Conway’s self-declared focus was politics, and he had spent four years shepherding through the courts a sexual harassment case against Clinton brought by Paula Jones, with funding from Republican (and later Clinton Foundation) donor Richard Mellon Scaife. At the same time, Conway or his associates had kept in touch with a court-appointed independent counsel investigating land deals by the Clintons in Arkansas: establishment Republican lawyer Kenneth Starr, whose probes had stalled. 

In early January 1998, after the Jones lawyers had finally been cleared to depose Clinton, one of Conway’s close legal associates acted as a conduit between the Lewinsky informant Linda Tripp and Starr. Based on the information about Clinton’s and Lewinsky’s affair that Tripp leaked to both Starr and the Jones’ attorneys, Lewinsky was questioned by the Independent Counsel’s office a day before President Clinton was questioned by the Jones attorneys, who raised the new issue of his alleged affair, which Clinton denied. One and two days after these coordinated depositions, Conway urged William Kristol to “break” the story on the ABC program This Week, which Kristol did. 

Nine days later, legitimized by the ensuing frenzy, Starr convened a federal grand jury, indicating that he might pursue charges against Clinton related to Clinton’s statement about Lewinsky, and eventually arguing that Clinton had perjured himself to the Jones attorneys, creating grounds for impeachment. In April, as reports of semen-stained dresses and a series of SNL satires created an “ick” factor while increasing the chances of impeachment, a Republican-appointed judge dismissed Jones’s years-long case as lacking merit. This meant that, in the eyes of the law, Clinton’s deposition should never have occurred in the first place. 

By November 1998, when public opinion had turned sharply against the impeachment process and the murky events leading up to it, most of Washington had doubled down on impeachment’s necessity. A headlining piece in the Washington Post by the wife of its former executive editor framed the “Washington insider” Starr as delivering a deserved comeuppance to Clinton, who in this read was a disrespectful populist who had failed to show “establishment Washington” the proper regard. Establishment-supporting voices in this article included commentator Michael Beschloss and the former Clinton White House aide turned Washington insider George Stephanopoulos, both reliable media “amplifiers” of the 2024 cases against Trump. 

Praised in the article (and contrasted with Clinton) for his regard for the Washington establishment was Rahm Emanuel, then a senior advisor to Clinton and later a major seeder, both personally and via a corporate Chicago connection, of Siskel’s career. Still, Clinton had his Washington defenders, among them Toobin, who wrote a book, A Vast Conspiracy, arguing that Starr’s, Conway’s, and Kristol’s moves amounted to a conspiracy to force a president from office, e.g. to “use the legal system to undo elections.”

These are all players, in other words, who, whatever side they landed in that earlier play, learned early the uses of running behind-the-scenes moves through the channel of the law. They got to see, up close and long before the rest of us, the helpfulness of seamy detail in generating scandal while discouraging a close look at facts. They understood how a compliant media and credentialed attorneys could take a thin case and give it momentum, legitimacy, and heft.

The political wheel has turned many times since the 1990s, so the image of Clinton as a challenger of establishment Washington seems like part of an alternative American history. But the players have stayed the same. So have their underlying loyalties, and so have their affinities with establishment reporters who write the narrative of the capital city. 

In 1998, Michael Isikoff of Newsweek, then owned by the Washington Post, painted George Conway’s work on the Jones case not as part of an insider play but as an outgrowth of Conway’s penchant for political gossip—a personal quirk. In 2024, POLITICO, a de facto spinoff of the Washington Post, broke news of the meetings arranged by Norman Eisen in a genially dismissive “expose”—allowing the group to avoid the appearance of impropriety that would have occurred had its meetings been revealed by opposition research. In the aftermath of the verdict in New York, the Times and POLITICO have both run pieces (one by the same author of POLITICO’s Eisen “expose,” a former prosecutor at the Department of Justice, and one by Norman Eisen himself, described as a “legal expert”) arguing that Trump and his attorneys “blew” or “bungled” the trial and discussing his possible imprisonment, rather than exploring the underlying interconnections or inconsistencies at play. 

Broader, more disquieting similarities between then and now exist as well. Twenty-five years ago last December, during the Clinton impeachment vote in the House, a Democratic congressman born in Puerto Rico likened the proceedings and what had led up to them to a golpe de estado: the overthrowing of a government, a coup d’etat. What he called a coup, and the one plausibly being run in 2024 by a fuller establishment contingent, have many of the characteristics of coups in other countries. These include capital city intrigue, private funding, committed insiders, unsavory “turncoats,” disregard of electoral processes, and manipulation of the legal system—all in the name of an apparently higher cause. But, unlike overthrow attempts abroad, these attempted coups are bloodless, and so in some ways more lethal. They do not come from the violent actors whom the law has always been thought to protect us against—the threats we think we know. Instead they come from credentialed lawyers minted in the universities, corporations and nonprofits whose authority flows from Washington, D.C. 

In some ways, the aptest diagnosis of this threat came a quarter century ago from Toobin himself, when he wrote in A Vast Conspiracy that “in the years since the Second World War, there has been a conspiracy within the legal system to take over the political system of the United States.”He traced this to liberals using courts and regulatory agencies to enact policy changes at the expense of representative government, beginning with the NAACP Legal Defense Fund, whose success in the 1950s made “feminists, environmentalists, and other activists” realize that “they didn’t have to do the expensive and labor-intensive work of persuading the masses to support their views.” Instead they could use lawsuits to change the political weather, a tactic that in the 1970s moved from political causes to include “good government” reforms empowering Washington lawyers to prevent another Watergate.

Toobin, a liberal legal reporter who had made his career off of this system of empowered operators, was criticizing its unintended late-20th century consequence: neoconservatives forming insider leagues of their own and using the Independent Counsel’s office, created by liberals after Watergate, to take out Clinton. 

When Toobin wrote, the postwar system itself seemed secure. Today, against the existential threat of a movement for representative government led by Trump, the system does not. In response, liberals and neoconservatives have doubled down behind it. They have aligned to form a legal wall in front of the deep state, which may or may not be able to eliminate a leader without firing a shot.



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