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As chief of staff to Sen. John Kerry (D-Mass.), David McKean has to put up with Washington lobbyists on a daily basis. That hasn’t prevented him, however, from spending much of his free time writing about two of the most infamous lobbyists of them all.

In 1995, McKean teamed with journalist Douglas Frantz to publish Friends in High Places: The Rise and Fall of Clark Clifford, a volume about the senior Democratic power broker who was the BCCI banking scandal’s most prominent casualty. In the course of researching the book, McKean kept coming across the name of another pioneering Washington lobbyist: Tommy “the Cork” Corcoran.

“Corcoran’s name kept popping up in different parts of Clifford’s life—as a friend, a competitor, or a social acquaintance,” says McKean, who recently published his second biography, Tommy the Cork: Washington’s Ultimate Insider From Roosevelt to Reagan.

McKean’s two subjects, it turned out, couldn’t have been more different. “[Clifford] always gave a speech to his prospective clients before they retained him, saying that…he would only provide them a strategic view of how to get something accomplished,” say the 47-year-old Cleveland Park resident. “He shrouded himself in the robes of statesmanship. Corcoran had no such pretensions. His basic pitch was, ‘If you want to get something done, I’m your man.’”

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Corcoran was born in Pawtucket, R.I., the son of a modestly successful politician. Around the start of World War II, he traded in his golden résumé—an undergraduate degree from Brown, a law degree from Harvard, a Supreme Court clerkship, a stint as a Wall Street lawyer, and an inside role crafting Franklin D. Roosevelt’s New Deal—for a practice in which he would advise clients less on the intricacies of the law and more on how to utilize inside influence. Indeed, Corcoran himself occasionally ignored those intricacies. In the early ’70s, he even tried to lobby Supreme Court Justices William Brennan and Hugo Black, hoping to bend their ears about a longstanding antitrust case.

Both justices immediately kicked Corcoran out of their offices, but the incident resurfaced in 1979, when Bob Woodward and Scott Armstrong published The Brethren: Inside the Supreme Court. Upon reading the book, Adm. Hyman Rickover, a prominent military man who had disliked Corcoran for decades, sent a letter to the District of Columbia Bar seeking an investigation.

“It turned out that Black had died by then, and Brennan didn’t remember, and Corcoran denied it, so he was absolved,” McKean says. “But a diary entry from Mrs. Black subsequently came out, and she reported that Hugo had come home very upset one day because Corcoran had come to visit him in the court and lobbied him on a pending case.”

Even so, Corcoran never wound up paying a price for his boldness. “He laughed easily and was always smiling,” says McKean. “He projected extraordinary energy….With his reputation as a Washington fixer, a lot of people forget how truly brilliant he was. He had one of the highest grades ever given out by Harvard Law School and clerked for Oliver Wendell Holmes on the Supreme Court. He was a fantastic writer—Roosevelt used him to write speeches, and in that job he coined the phrase ‘rendezvous with destiny.’”

Not everyone fell under Corcoran’s spell, however. President Truman took such a disliking to him that he ordered wiretaps placed on his phone—transcripts of which proved to be a gold mine for McKean. “On one of them,” the writer says, “he called Truman ‘dumb as hell.’”

Corcoran, of course, was smart enough to conduct most of his business elsewhere. “Corcoran had contacts in the Justice Department, so he eventually found out about the wiretaps,” McKean says. “He knew never to say anything incriminating on his office phone, so he went to the bank every morning to get 20 nickels for a dollar. If he had anything important to tell someone, he would go down to a phone booth to make the call. The only problem, he said, was that the nickels wore out his pockets.” —Louis Jacobson