Howie Carr Books in Order

If you want Boston crime fiction: Hard Knocks → Killers
If you want the Winter Hill Gang saga: The Brothers Bulger → Hitman → Rifleman → Ratman
If you want his take on national politics: What Really Happened

Howie Carr is best known as a sharp-tongued Boston radio host, but he has spent decades working both sides of the notebook, as a daily columnist, investigative reporter, and author of true crime and political books.

He was born in 1952 in Portland, Maine, to Frances Stokes Sutton and Howard Louis Carr Sr, and grew up following his parents’ hospitality and clerical jobs between Maine, Palm Beach in Florida, and Greensboro in North Carolina. That mix of working class roots and proximity to wealth shows up often in his writing.

As a teenager he landed at Deerfield Academy in western Massachusetts, where his mother worked for the headmaster and he attended on scholarship. After four years at Deerfield he was accepted to Brown University but chose the University of North Carolina at Chapel Hill instead, graduating Phi Beta Kappa in 1973 after writing for the student paper and studying journalism.

Carr started out at the Winston-Salem Journal, learning the pace of local news before heading back to New England. In Boston he joined the Herald American, first as an editor, then as City Hall and State House bureau chief, chasing mayors and legislators through budget fights, corruption cases, and the daily grind of city politics.

By the early 1980s he had become a regular presence for Boston readers and viewers, combining a tabloid columnist’s love of one liners with a reporter’s eye for documents. His drive time talk show, The Howie Carr Show, grew from a local WRKO program into a syndicated New England staple, mixing news, call in segments, and running feuds with familiar political targets.

Along the way he picked up a National Magazine Award for essays and criticism and, later, a spot in the National Radio Hall of Fame. However you feel about his politics, he has been hard to miss in New England media for more than forty years.

Carr’s books grew out of his long obsession with the Winter Hill Gang and Boston’s Irish mob. Living in Somerville in the 1970s, he watched the Bulger story unfold almost literally down the street, then spent years turning court files and interviews into narrative. The Brothers Bulger traces how Billy Bulger rose through the Massachusetts Senate while his brother Whitey ran a murderous crew, and what it meant when those worlds overlapped. Whitey was so angered by the coverage that he later told prison visitors he regretted not having Carr killed.

Later titles pushed deeper into that underworld. Hitman follows Johnny Martorano, the Winter Hill killer who admitted to twenty mob murders. Rifleman centers on Stevie Flemmi, Whitey Bulger’s longtime partner and a lifelong government informant. Ratman and Plug Uglies return to the Bulger saga with trial reporting, photographs, and archival material that show how law enforcement, politics, and organized crime collided in Boston.

In between the nonfiction, Carr has written crime novels such as Hard Knocks and Killers, which drop a disgraced ex cop and Boston mobsters into bare knuckled stories about State House deals and street level violence. The tone is familiar to anyone who listens to his show, full of Boston slang, local references, and a dark sense of humor.

In recent years he has shifted more of his attention to national politics, writing What Really Happened about the 2016 election and Donald Trump’s path to the White House. The book reflects his seat at rallies, town halls, and private flights during that campaign and his unapologetically conservative point of view.

Carr and his wife Kathy Stimpson have three daughters together, and he has two older daughters from his first marriage. He has long made his home in Wellesley, Massachusetts, while also spending substantial time in Florida, and he continues to juggle columns, radio, and books about crime, politics, and the characters who inhabit both worlds.