The revelation of Brad Karp’s association with sex criminal Jeffrey Epstein marks an unseemly end to an almost novelistic Wall Street success story. In his 18 years as chair of Paul, Weiss, Rifkind, Wharton & Garrison, Karp gained wide admiration for how he marshalled his firm from Wall Street distinction to global notability. For a man who had been serially lauded for his tactical leadership, his political nous and apparent social conscience, it is an ugly mutation of what just a couple of years ago many would have anticipated as the legacy ideal. The controversy ended his chairmanship and triggered the beginning of the Scott Barshay era at Paul Weiss, but perhaps without the double-underlined finality you might expect in such a situation, given that Karp remains a partner at the firm. Email exchanges reveal that Karp had coordinated with Epstein on multiple occasions to track the whereabouts of a woman ostensibly connected to Karp’s and Epstein’s mutual client Leon Black, the former Apollo boss; they alluded to multiple dinners they shared, and a meeting Karp wanted Epstein to broker between Karp’s son and director Woody Allen; at one point, Karp described the convicted pedophile as “amazing." Karp also emailed Epstein to discuss a draft motion intended to prevent the reopening of Epstein’s 2008 non-prosecution agreement. Karp has stated that his dealings with Epstein specifically related to a fee dispute between Epstein and Black. Paul Weiss has also stressed that Karp has not been accused of any misconduct. Beyond the obvious, there’s a nagging question here: why didn’t Karp quit sooner? How could he not have anticipated that his ties to Epstein would, sooner or later, see the light of day? The timing of the release of the Justice Department's Epstein files was always uncertain. Months, years. No one was sure. But there was a wide feeling that they would at some point emerge, a fact made clearer once the Epstein Files Transparency Act passed a Congressional vote in November. Paul Weiss has said that Epstein was not a client of the firm’s, rather that the Karp-Epstein tie was a byproduct of Karp’s representation of Black. Given the nature of the association—a charitable view is that it was more tangential and less immediate than if Epstein had been a client—it’s feasible that Karp hadn’t anticipated that his name, or indeed his Paul Weiss-signatured emails, would appear in the latest revelatory bundle. Yet in the cold light of reputation management, a purely strategic move would have seen Karp first anticipate the Epstein files release, and second, play out his resignation under the cover of the Trump deal maelstrom. Let’s put it this way: a headline that reads "Former Paul Weiss Leader Named in Epstein Files" would likely have presented fewer reputational challenges, on most fronts, to either Karp or his firm. If Paul Weiss, or Karp, had been advising a client, it feels like the kind of thing they’d have closely considered. This is, after all, the second time that Paul Weiss, and Karp, have made global headlines in the past 12 months. Less than a year ago, last March, the firm’s reputation as a storied defender of egalitarian and judicial values suffered when it pioneered a deal with President Trump that broadly split observers into the two camps: "commercial necessity" or "hypocritical dereliction of duty." Paul Weiss’ business-led assertions at the time fell awkwardly against the firm’s pro bono record of acting on causes antithetical to Trumpist ideology, such as fighting the administration's policy of separating children from their parents at the border, and Karp’s previous exaltations on the rule of law. Some viewed the Trump deal as Karp’s capitulation to a bully that paved the way for other large law firms to also brusquely surrender their principles. Some felt it was a repudiation of the firm’s stated principle, courtesy of name partner Simon H. Rifkind, of “achieving our objectives without wearing any client’s collar or any political party’s livery." Karp defended the move as necessary in navigating what he called an “existential crisis." Karp's Trump deal had the air of conspiring with the enemy: here was a man who seemed to embody everything that Trump wasn’t, one who had spent his adult life petitioning for causes that the Trump administration today decries, and a lifelong Democrat and a fundraiser for once-presidential hopeful Kamala Harris. It is certainly possible that if he had stepped down immediately after the deal, he’d have absorbed any blowback while steering his firm out of harm’s way. And few would have seen such a resignation as undignified. Who’d have blamed him after a year he’d described as “incredibly painful and difficult” and “the most challenging year in my life”—one in which he’d suffered a heart attack. In this scenario, the sensation around Karp’s hypothetical earlier resignation might even have smothered the sideline snipes that remind us that the decision to strike the deal had, in fact, received partnership approval. For such a long-tenured, shrewd leader—one noted for his skill in navigating crises and managing the media—the failure to anticipate publicity around his involvement with Epstein, and its likely impact, is jarring. At best, it is what one insider called “poor judgment," and at worst, it was a hubristic act to hold onto power despite the huge reputational, even moral, implications. And what of his legacy? Since becoming a summer associate in 1983, Karp spent his entire career at Paul Weiss, becoming chair in 2008. In an era of withering firm loyalty, his career story was almost romantic in its virtues of traditional but ambitious leadership, and in his devotion to a single firm. Instead, its ending has brought unwanted attention to the very institution he claimed to protect.