Laurence Silberman

Some politically hostile commentators have speculated that Silberman may have been involved in the so-called "October Surprise" with respect to the Iran hostage crisis prior to the 1980 presidential election, alleging that Silberman and others had attended meetings to negotiate the delayed release of the hostages by the Iranian government.[27]

Silberman has publicly responded as follows to the allegations:

In the early fall of 1980 when I was Co-Chairman of Governor Reagan's foreign policy advisors and then a San Francisco banker, I came back to Washington for a meeting of Governor Reagan's advisors. Dick Allen, who subsequently became President Reagan's National Security Advisor, was playing a similar role in the campaign. As our session ended (I recall it dealt with Arab-Israeli issues), Dick asked me if I could accompany him to a meeting at the L'Enfant Hotel. He explained that Bud McFarlane, then working for Senator Tower, wished him to see someone who had information on the hostage crisis—which, of course, was a matter of great political consequence to both campaigns. He asked me to join him, as an ex-Deputy Attorney General, because he was a bit apprehensive. At about noon McFarlane walked into the lobby with a gentleman whom I remembered as a Moroccan. But, as Dick Allen's contemporaneously-written memorandum had it, the man was a Malaysian named Mohammed (at least I got the "M" right). He was a fervent supporter of the Shah and an adversary of the Iranian revolution, but he was definitely not an Iranian, still less a representative of the Iranian government [the contrary of which assertion being the essence of the allegations of inappropriate contact with the Iranian government]. He was also hostile to the Carter Administration for having abandoned the Shah. It was his plan to contact someone with influence in Iran to propose that the hostages be released before the election to Governor Reagan, thereby embarrassing President Carter. I was shocked and responded spontaneously that we Americans have only one President at a time, and although Dick asked him for any actual information he might have on the hostages—which he did not have—we left after only a few minutes. I advised Dick to write a memo of the meeting, which he did. Unfortunately the memo, subsequently authenticated by the FBI, was mislaid for years. Ironically, it was I who unwittingly initiated the so-called "October Surprise" story, which grew into an utterly fantastic tale, even including George H. W. Bush's alleged secret trips to Paris to meet with Iranian emissaries. Bill Safire heard something of the L'Enfant Plaza meeting when he was doing a rather critical story on McFarlane, who had been Reagan's National Security Advisor. He called me (I was by then on the bench), and I told him what occurred. He made brief mention of it in a column raising, perhaps, unfair questions about McFarlane's judgment—it may well be that McFarlane was acting for Senator Tower.[28]

On January 3, 1993, the bipartisan Joint Report of the Task Force to Investigate Certain Allegations Concerning the Holding of American Hostages by Iran in 1980, also known as the "October Surprise Task Force," was released. The Task Force, led by Rep. Lee H. Hamilton (D) and Rep. Henry J. Hyde (R), specifically concluded that "there is wholly insufficient evidence of any communications by or on behalf of the 1980 Reagan Presidential campaign with any persons representing or connected with the Iranian government or with those holding Americans as hostages during the 1979-1981 period" and that "there is no credible evidence supporting any attempt or proposal to attempt, by the Reagan Presidential Campaign—or persons representing or associated with the campaign—to delay the release of the American hostages in Iran."[29]

Silberman served on a panel of the D.C. Circuit in U.S. vs. Oliver L. North, 910 F.2d 843 (1990), in which a per curiam opinion was issued that overturned the conviction of Oliver North, who had been a key figure in perpetrating the Iran-Contra Affair.

In his memoir, Firewall, published seven years after the case in 1997, Lawrence Walsh, the Independent Counsel appointed by President Reagan to investigate the Iran-Contra affair, mused that in retrospect, he wishes that he had moved for Silberman's recusal from the panel:

Yet I was reluctant to request that Silberman disqualify himself. Prior government service or political activity did not bar him from serving on the panel. His unfavorable view of independent counsel, if it arose in the course of litigation rather than outside the courtroom, was not a basis for disqualification. Too late, I learned that he had a personal animus: He despised Judge Gerhardt Gesell [who presided over the North case in the lower court]. Indeed, Silberman had stopped having lunch in the judges' lunchroom because of his antipathy for Gesell. Had I known that, the scales certainly would have tipped in favor of my seeking his recusal.[30][31]

Silberman has also observed that David Brock, latterly a Silberman critic (see below), has published a refutation of Lawrence Walsh's characterization of Judge Silberman's involvement in the North case:

I am still gratified, however, by Brock's review of Lawrence Walsh's book, which he has never (or at least, not yet) repudiated. In that review, Brock, by interviewing federal judges, demolished Walsh's bizarre and unique claim that I should have recused myself from sitting on the North case because of my supposed hostility to the federal district judge who decided the case. As Brock established, that assertion—which no one ever heard of as a ground for recusal—was untrue.[32]

In his book Blinded by the Right: The Conscience of an Ex-Conservative, David Brock dedicates several pages to criticizing Silberman.

In 2006, Silberman responded to Brock's allegations in a posting on Michael Barone's U.S. News & World Report blog.[33]

On June 15, 2020, The Intercept reported on an email exchanged initiated by Silberman and focused on Confederate statutes. In his email to all staff at the court, Silberman wrote, “Since I am about to be interviewed I thought it would be appropriate to unburden myself in opposition to the madness proposed by Senator Warren: the desecration of Confederate graves.” He went on to say, “It’s important to remember that Lincoln did not fight the war to free the Slaves [sic] Indeed he was willing to put up with slavery if the Confederate States Returned [sic],” and went on “My great great grandfather Never owned slaves as best I can tell.”

The email went unanswered for roughly a day, until a clerk responded saying, “I am one of only five black law clerks in this entire circuit. However, the views I express below are solely my own.” The clerk went on, “[s]ince no one in the court’s leadership has responded to your message, I thought I would give it a try.” The response included an analysis of how a newly freed slave would view Lincoln vis-a-vis Silberman's comments, as well as the point of view that the Confederacy was at its heart about supporting slavery and that in the end the Confederacy was defeated. The clerk ended his email by using Silberman's own legal writings and logic. "...I will note that the current movement to rename Government owned facilities is in line with your previous opinions on the importance of names and what they represent. In 2005, you publicly advocated for the removal of J. Edgar Hoover’s name from the FBI Building due to the problematic material you came across in your review of his FBI files after his death. You equated it to the Defense Department being named for Aaron Burr. In view of your opinion of J. Edgar Hoover’s history and your advocacy for renaming the FBI building because of the prominence it provides Hoover’s legacy, it is very strange that you would be against renaming our military facilities, since the legacy of the Confederacy represents the same thing. This moment of confronting our nation’s racial history is too big to be disregarded based on familial ties."