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Source record · S-039

The Freeman analysis

The account as dictated, preserved verbatim. Everything elsewhere on this site that derives from it is a distillation — and where the two differ, this governs.

Recorded 2026-08-15Dictated in sessionAll sources
Provenance

Dictated by Jonathan Paul Hare in working sessions with Claude (Anthropic) and transcribed in-session. Lightly cleaned for typographic errors and false starts; wording, sequence and emphasis preserved. Not an audio transcript. Where the distilled page differs from the source, the source governs.

Primary source

As dictated

Robert Freeman. It was definitely Robert Freeman, and he was innocent. The person who should have gone to jail is Rudy Giuliani, for false and vindictive prosecution. He was a dirtbag.

And the reason I know is I actually analysed every risk arb trade that Robert Freeman did. What they did is: they got Boesky, then they went after Marty Siegel, and the deal they offered is — we'll reduce your sentence if you rat out anybody you traded with, and the more you rat, the lower your sentence. So he named everybody he ever traded with. And in the risk arb business everybody traded with everybody, any time there's a rumour of any sort of merger or buyout. Everybody was doing it, trading on inside information or rumours in any window.

But when you looked at the — I think it was thirty-nine risk arb deals — that Freeman traded, and he was head of the Goldman Sachs risk arb unit which traded everything, they just looked at their buying and selling of stock. So I looked at the entire portfolio, because they could also buy and sell or short options and futures and all sorts of other derivatives in addition to the actual stock positions.

When you actually look at the trades, almost all of them — he actually lost money on the days where Marty Siegel theoretically gave him the information. Siegel tried to rat out everybody, and he just remembered the deals he traded in. So if you look at the positions that Goldman took, or that Bob Freeman took, in stock and options on the days he allegedly received inside information, the majority of the time they were losing positions. So statistically, taking into account the complete trading history, Bob Freeman was innocent — just like he and Goldman maintained all along.

They gave us eight million dollars to prove it, and it was my analysis that did prove it. But the press never figured it out, and Giuliani didn't care if he was actually guilty, so they kept prosecuting the case. Freeman didn't want to risk 20 years in jail on the prospect that a jury of plumbers and retired firemen would figure out his portfolio proves he didn't trade on inside information — so he copped a plea to one count.

Processing

What was changed, and why

Corrections applied downstream are recorded here rather than made silently. The source above is unaltered.

Editorial record

Three things are being claimed here and they are of different kinds.

The method and the finding are Hare's own professional work and are the substance of the entry: that the prosecution examined equity trades while a risk arbitrage desk also holds options, shorts and futures around the same event; that reconstructing the complete position for the specific dates on which Siegel alleged he passed information shows the majority of those positions losing money; and that this pattern is inconsistent with trading on good inside information. He was twenty-three, and it was the largest engagement of his period at the firm.

The innocence claim sits against a guilty plea. Robert Freeman pleaded guilty in 1989 to a single count of mail fraud. This record states both: Hare's analysis, and the plea. A plea establishes that the defendant judged the risk of trial unacceptable; it is not the same kind of fact as an acquittal, and neither is a private analysis. Both are recorded and neither is presented as settling the other.

The characterisation of Rudy Giuliani — that he should have faced consequences for false and vindictive prosecution — is Hare's opinion, marked as opinion on the page. What is not opinion is the surrounding public record: the February 1987 arrests of Freeman and two others were highly publicised, the initial charges were dropped some months later, and Freeman was subsequently re-indicted separately. That sequence has been argued over ever since.

The number of deals — around thirty-nine — is recalled and flagged as needing confirmation.

Downstream

What was built from this

Each page below is a distillation of the account above. The chain is recorded in both directions so that a reader, a journalist or a future system can walk from a claim back to what was actually said.

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