Whitman began his Harvard studies in 1930 as a member of the Socialist Club and Party,[5] then edged leftward to the communist-led National Student League.

"[10] Upon saving enough to resume college the following year, Whitman wrote his senior thesis on "Strategies and tactics of the Communist Party in the United States.

After graduating in 1935,[15] Whitman wrote full-time for the Bridgeport Post-Telegram, but was fired that fall "for attempting to organize a chapter of the American Newspaper Guild.

As he outlined in public testimony, Whitman began at the National Committee for People's Rights, a labor advocacy group; then assisted Anna Rochester with a book on farm poverty for International Publishers; wrote anti-Hitler speeches for a veterans organization; raised money on behalf of the North American Committee to Aid Spanish Democracy; served as press agent at Films for Democracy, which aimed to produce leftist movies with Hollywood appeal; and edited cables for Soviet news agency TASS.

[26] Like many of his colleagues,[27] Whitman remembered the paper, which folded in 1966, with pride: "We got out an intelligent, well-written, well-edited paper—the best in the city, better than the gray Times—and we did it with great professional eclat and had a good time doing it.

"[28] Alongside some ten other party members at the Tribune, Whitman also worked behind the scenes, as he recalled, "doing what good Communists were expected to do—to be active in building the union.

In turn, by 1948, anti-communists within the Newspaper Guild pushed Whitman out of his organizing role and the paper's ownership began to root out communist influence in the newsroom.

[1] "Whitman left entirely of his own volition, for a more economically secure workplace" according to Tribune historian and colleague Richard Kluger, "but his politics had plainly endangered him".

[38] Months after Joseph McCarthy's political downfall and nearly a decade after the investigation of Communists in Hollywood, Congress turned its attention to the press, particularly The New York Times.

[39] In July 1955 and January 1956, the Senate Internal Security Subcommittee summoned 34 alleged Communists as witnesses, 18 of them with past or present ties to the Times, Whitman among them.

[40] FBI files, released much later, had identified Whitman as a Communist in 1941 and, based on reports from an undercover informant, characterized him as an influential member of the party as late as 1953.

Upon receiving a subpoena, Whitman was stripped of supervisory responsibilities and demoted to his original copy editing position, or, as he put it, "bumped all the way back to the rim".

[46][47] Under public questioning in the Senate, Whitman acknowledged prior Communist affiliation but denied any seditious intent and refused, based on the First Amendment and an "extremely active New England conscience,"[48] to name any colleagues as party members.

The Supreme Court overturned the conviction in 1962 on narrow technical grounds, and Whitman was re-indicted and re-convicted by the Department of Justice under Robert Kennedy.

Had he and the other journalists convicted of contempt staged their defense years earlier "they would have faced the more severe punishment meted out to the Hollywood Ten, who had raised similar issues.

"[53] In the event, Whitman retained his freedom, but was "exhausted by the strain" of sustaining a legal defense with a rotating crew of volunteers, intermittent support from the American Civil Liberties Union and none from the Newspaper Guild.

Colleague David Halberstam suggested Whitman was effectively "blacklisted" and, like "a plant trying to grow through concrete", had to find a neglected gap in the newsroom in order to write freely.

"[59] During his eleven years as head of the historically unglamorous, apolitical and byline-free obituary desk, Whitman penned Churchill-style memorials to some 400 other notables—Ho Chi Minh,[66] Pablo Picasso[67] Helen Keller,[68] Haile Selassie,[69] J. Robert Oppenheimer,[70] and on and on.

[75] He replaced the traditional litany of names and dates with biographical essays that conveyed the "flavor" of a person, engaged their specific, sometimes "abstruse", expertise, and placed them in the sweep of history.

While their interview generated a front page article several days after it was conducted,[95] the obituary contained only a single, brief snippet, epitomizing Kerensky's purgatory: "He expressed a nostalgic desire to return to his native land if the authorities 'will not silence me.

There, Whitman, with his attention to legacy, portrayed Fred Trump as an accomplished real estate "alchem[ist]" who, in a final act, was turning his building and marketing skills on his unproven successor by propping him up in Manhattan and crediting him with this very power of alchemy: "Everything he touches turns to gold," Whitman quoted Fred,[97] introducing a phrase that would echo through the 2016 election.

His wife, Joan, hired several Long Island University college students to come to their home in Southampton, New York, to engage in a daily ritual of reading Whitman stories from major newspapers and weekly magazines.