Having freelanced for Radio Telefís Éireann while at UCD, he was appointed their London correspondent in 1968, before working at the Conservative Research Department from 1969, where he became a Zionist. He became political editor of
The Spectator in 1971, where his numerous, often scathing, articles about Ted Heath's leadership were influential in effecting the change to Margaret Thatcher, and earned him the nickname "The Mekon".
When Thatcher first saw him speaking on television, she reportedly dismissed him as a "typical upper-class public school twit", to his subsequent delight. In 1975, he became her advisor while she was Leader of the Opposition. He seemed on the path to a safe seat in Parliament and ultimately a cabinet post. However, Thatcher dropped him after winning power in the 1979 general election, by which time his heavy drinking was impairing his reliability.
Private Eye suggested Thatcher dropped him because had vomited on her in a taxi, though the story is disputed.
Subsequently he was briefly editor-in-chief of Tiny Rowland's Lonrho publications. He had first attracted Rowland's attention in 1973 after criticising in
The Spectator Ted Heath's calling Lonrho "the unacceptable face of capitalism". After this, earning a precarious living as a freelance journalist and by writing books, mainly political biographies. Among other publications, he wrote for
The Times,
The Daily Telegraph,
The Independent,
The Irish Times,
The Irish Press, the
Literary Review,
Encounter, the
New Law Journal, and
Le Point.
Books
Cosgrave's first book was a review of the poetry of Robert Lowell.
reprinted in
[[Martin Seymour-Smith]] derided the book, but Lowell agreed with Cosgrave's criticism of "Mr Edwards and the Spider", and dedicated a rewritten version to him.
His 1978 biography of Margaret Thatcher was faulted for hero-worship; George Gale called it "not much above a hagiography". His biography of Enoch Powell, whom he also admired, was made with access to Powell and his correspondence, and was the work of which he was most proud. He completed only the first volume of a planned two-volume study of Winston Churchill during World War II.
He published three mystery novels featuring the daring Colonel Allen Cheyney.