Zilkha's lawyer and a Samberg spokesman declined to explain the payments or to answer any questions from Condé Nast Portfolio about them, and so far neither Zilkha nor Samberg have provided an explanation in court.
The Senate Judiciary Committee has obtained the documents from the divorce case and is monitoring developments in court to see if there is any evidence that the payments to Zilkha are related to the insider-trading investigation.
In a 2007 report, the Judiciary Committee and the Finance Committee criticized the S.E.C.'s investigation of suspicions that Samberg had inside information when he made particularly profitable trades in several companies' securities.
One part of the S.E.C. investigation centered on suspicion that Zilkha had given Samberg insider information about Microsoft which he used to make a quick $12 million profit in April 2001, according to commission records.
A separate facet of the S.E.C. investigation looked into whether Morgan Stanley C.E.O. John Mack had fed inside information to Samberg about a planned General Electric acquisition of Heller Financial, a lender to businesses. Samberg's hedge fund had bought Heller shares and shorted G.E. stock in advance of the announcement, and made $18 million on the trading, the S.E.C. said.
The Mack aspect of the case hit the headlines because the S.E.C. fired the government lawyer investigating the allegations, Gary Aguirre. Aguirre claimed he was fired for insisting on subpoenaing Mack, a move which he said higher-ups at the S.E.C. overruled because of Mack's connections and political clout.
The S.E.C. denied that, but a joint investigation by the Senate judiciary and finance committees in August 2007 sided with Aguirre and sharply faulted the S.E.C. for failing to pursue the case, including the evidence concerning Zilkha and Samberg’s Microsoft trading.
In a report issued in October 2008, the S.E.C.'s own inspector general recommended disciplining senior S.E.C. officials for their handling of the case. A month later, however, an S.E.C. administrative law judge ruled against any disciplinary measures.
The trading investigated in the case occurred in 2001. Zilkha had been working as a product manager at Microsoft when Samberg that year offered him a job as an analyst of technology stocks at Pequot.
Records made public in the investigation show that in February 2001, in the same email in which he offered Zilkha a job, Samberg pressed him for information about Microsoft. Zilkha then was still employed by Microsoft. The email said "might as well pick your brain before you go on the payroll!"
On April 6, 2001, Samberg in an email pressed Zilkha for any "tidbits" about Microsoft. Zilkha responded the next day that he would get back to Samberg "ASAP."
Three days later, Samberg, who had been betting that Microsoft's stock would go down, reversed course and began amassing 30,000 Microsoft options in a bet the stock would go up, according to S.E.C. records from the case.
On April 17, Zilkha reported in an email to Samberg that Microsoft's chief financial officer had been unusually upbeat in advance of the company's pending quarterly earnings announcement. The email appears in S.E.C. files.
Microsoft announced its earnings on April 19, beating analysts' expectations. The stock rose, and a day later Samberg closed out his positions, reaping that $12 million profit. That day, Samberg emailed Zilkha that "I shouldn't say this, but you probably have paid for yourself already," investigators found.
Samberg fired Zilkha months later in 2001, after Zilkha's contacts inside Microsoft evidently had stopped talking to him, according to records from the S.E.C. investigation.
After that, Zilkha had no known personal or financial dealings with Samberg or Pequot.