As Conrad Black's troubles mounted two years ago, culminating in criminal convictions and a prison sentence, many of his prominent friends melted away.
But a small group stuck with him, travelling to a Florida prison for visits and monitoring his appeals.
Among them: Roger Hertog, a wealthy New York philanthropist who shares Lord Black's dedication to conservative causes.
On Wednesday, Mr. Hertog took their friendship a step further, putting $2-million (U.S.) on the line to secure Lord Black's release from prison.
Mr. Hertog "is a very dear friend" of Lord Black's, said R. Emmett Tyrrell, Jr., editor-in-chief of The American Spectator, a conservative monthly magazine. Mr. Tyrrell visited Lord Black in prison once; Mr. Hertog went several times, he says.
"Roger takes the law of this land very seriously, especially an unconstitutional law," Mr. Tyrrell said. "He thought, as I did, and Conrad did, that the law was unconstitutional and the incarceration was unconstitutional."
The relationship between Mr. Hertog and Lord Black was forged in a joint business venture, the ill-fated New York Sun, and nurtured through a common social circle. On a slender spit of oceanfront land in tony Palm Beach, Fla., Lord Black's villa is a five-minute drive from a home owned by Mr. Hertog and his wife.
While the two men differ in temperament - where Lord Black can be bombastic, Mr. Hertog is low-key - they are "peas in a pod" when it comes to intellectual pursuits, says a person who knows them both. They share a devotion to newspapers, conservative politics and the vigorous debate of ideas.
It's unclear how the arrangement to secure Lord Black's release originated, but it's little surprise that Mr. Hertog is playing a starring role, says the person. The friends who stood by Lord Black are a "relatively small group," he said. "It's an even smaller group who can put their hands on $2-million."
In a Chicago courtroom on Wednesday, Miguel Estrada, one of Lord Black's lawyers, could be overheard thanking Mr. Hertog profusely for guaranteeing the bail. During the hearing, Mr. Hertog confirmed to a judge that he understood the terms of the agreement and signed it. Later he left the courtroom alone, briefcase in hand, declining to talk with reporters.
Born in 1941 in the Bronx to a family of German-Jewish immigrants, Mr. Hertog attended the City College of New York, then free for deserving students, giving it the nickname the "poor man's Harvard." Although he went on to become a member of the conservative intelligentsia, his early priorities were "money and girls," he said two years ago. "Ideas came in third."
Mr. Hertog built his fortune in the investment business, helping to build Sanford Bernstein & Co., a brokerage firm. It was sold in 2000 and now forms part of asset manager AllianceBernstein LP.
Long before his retirement from the firm in 2006, Mr. Hertog was already an energetic benefactor. He supports a wide collection of educational and cultural institutions, including the New York Historical Society, which he chairs, the New York Public Library, and the New York Philharmonic. In 2007, he received the National Humanities Medal for his philanthropy in a ceremony with president George W. Bush.
Another major thrust to his giving is ideological. Recipients of his largesse include conservative think tanks such as the Manhattan Institute in New York and the American Enterprise Institute for Public Policy Research in Washington.
He was also an early supporter of the New York Sun, a newspaper founded in 2002 with the somewhat quixotic goal of building a conservative readership base in one of the country's most liberal cities. The venture brought together Mr. Hertog and Lord Black, whose Hollinger Inc. took a stake in the paper. Other backers included hedge fund managers Bruce Kovner and Michael Steinhardt.
The paper folded in 2008. Seth Lipsky, the former editor of the Sun and a staunch defender of Lord Black, declined to comment.
Mr. Hertog once described his credo as "Free markets, free minds, all that stuff." Although steeped in conservative thought, Mr. Hertog told an interviewer in 2002 that he wasn't "a particularly partisan person," and was rarely involved in political campaigns. "It's never interested me," he said. "What interested me was ideas."
With a report from Paul Waldie in Chicago