Kirkland & Ellis is not representing accused sexual predator Jeffrey Epstein this time around, but the law firm and its alumni's prints are all over his current criminal case in New York federal court.

Epstein's criminal case history includes several Kirkland litigators, past and present, including longtime partner Jay Lefkowitz and former Kirkland litigators Alexander Acosta, now U.S. labour secretary, and Kenneth Starr.

With Epstein's arrest on July 6 for sex trafficking, and a government investigation into a plea deal reached by Epstein's attorneys in 2007, actions by those Kirkland litigators will likely receive fresh scrutiny.

In particular, legal ethics experts told ALM that a 2007 meeting between Lefkowitz, one of Epstein's defense lawyers at the time, and Acosta, then the top federal prosecutor in Miami, would likely be of interest to the Justice Department, which announced in February it was investigating how Epstein's prior criminal case was resolved.

"The fact of the remote meeting with a former colleague of Acosta's will certainly be an issue in DOJ's review of how the plea deal was reached," said Stephen Gillers, a legal ethics professor at New York University School of Law, adding: "Put simply, it is suspicious."

New sex trafficking charges against Epstein were revealed on Monday in Manhattan. Prosecutors said they were not bound by the earlier plea agreement negotiated by Acosta. Reid Weingarten, a partner at Steptoe & Johnson LLP, as well as Martin Weinberg and Marc Allan Fernich, who run their own firms, represent Epstein in the New York case.

In a statement on Monday, Kirkland said it no longer represents Epstein. "Kirkland & Ellis has not represented Jeffrey Epstein in eight years and has no involvement in his current case," said a Kirkland spokesperson, declining to comment further.

A private meeting

Kirkland's previous representation of Epstein, in a sex crimes case, is distinct from its usual clientele of large corporations and private equity firms in government enforcement litigation.

At the time Kirkland and others were representing Epstein in 2007, he was facing a draft 53-page federal indictment with allegations that he had built a network of underage girls to coerce into performing sex acts, according to the Miami Herald's reporting.

In October that year, Acosta, the Miami U.S. lawyer who was previously a litigator at Kirkland, met with Lefkowitz, a longtime a partner at the firm, to negotiate issues related to a non-prosecution agreement, according to the Herald. Instead of meeting at the prosecutor's Miami headquarters, the two former colleagues met at the Marriott in West Palm Beach, about 70 miles away, where a deal was struck, the Herald reported.

The agreement required Epstein, a wealthy money manager, to plead guilty to state prostitution charges that ultimately only resulted in 13 months behind bars. Even then, Epstein was free for up to 16 hours a day for much of his sentence.

In a letter sent by Lefkowitz memorialising the meeting, the Herald reported, he thanked Acosta for working out a deal that included a commitment by the U.S. lawyer not to contact "any of the identified individuals, potential witnesses or potential civil claimants" against Epstein.

Several legal ethics experts told ALM that Acosta meeting with a former colleague at Kirkland to hammer out the resolution of a case wasn't itself an ethical concern – but the circumstances and the location of the setting were troubling.

Defense lawyers regularly negotiate with prosecutors who are former colleagues, said John B. Harris, a partner at Frankfurt Kurnit Klein & Selz who focuses on legal ethics, professional liability and white-collar defense matters.

But he said: "That a prosecutor and a defense lawyer would meet privately at a hotel over breakfast to negotiate a deal for the defense lawyer's client is unusual and smacks of preferential treatment. Most defense attorneys meet with prosecutors, including the prosecutors actually handling the case, at the prosecutor's offices during regular business hours."

Similarly, Gillers said, holding a meeting at a "remote location will inevitably suggest special treatment in the public's mind and the appearance that Acosta was trying to hide his conduct".

These events, ethics expert said, will likely weigh into the Justice Department's investigation of how the Florida case was handled, meaning more questions could be asked of Kirkland.

The Justice Department has said that its Office of Professional Responsibility (OPR) would investigate "allegations that department attorneys may have committed professional misconduct in the manner in which the Epstein criminal matter was resolved". According to DOJ guidance, the OPR's investigation process, in general, includes obtaining relevant documents and conducting witness interviews, but the OPR does not have authority to issue witness or document subpoenas to non-department personnel.

"An investigator," Harris said, "might well be interested in examples of favourable treatment received by well-connected defense lawyers, especially given the hands-on involvement of the U.S. attorney himself." And, Harris said, it makes sense "that an investigator would want to know what private conversations the U.S. attorney and a defense lawyer had about the deal and what possible influences or inducements could have affected the resolution".

A bevy of lawyers

Lefkowitz represented Epstein along with other titans of the defense bar, such as Roy Black, Gerald Lefcourt, Alan Dershowitz and his Kirkland colleague Kenneth Starr, who had previously helped recruit Acosta to Kirkland in the 1990s. Starr was a partner at Kirkland from 1993 until 2004 and remained counsel to the firm until at least 2010.

Lefkowitz, who joined Kirkland in 1993, continued to represent Epstein as recently as 2011 in a New York state court proceeding regarding his sex-offender status, court records show.

Acosta, who worked at Kirkland from 1995 to 1997, has repeatedly faced criticism for his role in the non-prosecution agreement. The deal was not revealed to Epstein's alleged victims, which a federal judge has deemed a violation of the Crime Victims Rights Act.

Acosta has defended his office's work, saying it ensured Epstein received time behind bars.

In a 2011 letter published by The Daily Beast, he said Epstein's "army of legal superstars" went so far as to investigate the personal lives of prosecutors in search of material that could be used to disqualify them.

In the letter, Acosta said he had known Dershowitz, Starr and Lefkowitz "from my time in law school and at Kirkland & Ellis in the mid-90s", adding: "They all sought to make peace. I agreed to talk and meet with all of them after Epstein pled guilty, as I think it is important that prosecutors battle defense attorneys in a case and then move on. I have tried, yet I confess that has been difficult to do fully in this case."

Meanwhile, another Kirkland alum may be jumping into the newest Epstein case.

Attorney General William Barr is recused from any review of the earlier plea deal that allowed Epstein to avoid federal charges in Florida. But Barr, who practised at Kirkland in 2009 and then again in 2017 until 2019, has consulted with Justice Department ethics officials and will not recuse himself from overseeing Epstein's new criminal case, The Associated Press and others reported.