Journalism Carr began his career as a reporter for the
Winston-Salem Journal before returning to New England in 1979 as assistant city
editor for the
Boston Herald American (now the
Boston Herald). From 1980 to 1981, he was the Boston City Hall bureau chief of the
Herald American, and he later worked as the paper's State House bureau chief. As a political reporter for WNEV (now
WHDH) in 1982, his coverage of then-mayor
Kevin White was so relentless that after the mayor announced he was not running again, he told
The Boston Globe that one of the things he enjoyed most about his impending retirement was not having Carr chase him around the city. Carr has criticized former
Globe and
Herald guest columnist
Mike Barnicle for years. In 1998, Barnicle resigned from the
Globe over allegations of plagiarism and fabrication of stories. A
Globe column by Steve Bailey stated that Carr gave out Barnicle's home phone number, an allegation Carr denies. Barnicle called Carr "a pathetic figure", and asked "Can you imagine being as consumed with envy and jealousy toward me for as long as it has consumed him?" In 1998,
Don Imus claimed Carr's wife was having an affair with boxer
Riddick Bowe. Mrs. Carr retained
Alan Dershowitz as her lawyer. The parties reached an undisclosed settlement. In a 2007 column, Carr alleged that Barnicle incited Imus' statements. According to Carr, Barnicle told Imus that Carr had said Imus "would die before his kid got out of high school". In 2002, the
Herald and Carr were the subjects of a lawsuit by Superior Court Judge Ernest Murphy. The newspaper reported that Murphy had said of a fourteen-year-old rape victim: "She can't go through life as a victim. She's 14. She got raped. Tell her to get over it." He was also alleged to have said of a 79-year-old robbery victim: "I don't care if she's 109." Carr, in a front-page column on February 20, 2002, criticized Murphy for setting low cash bails in rape cases and included references to his daughters, wondering what Murphy would do if it were one of
his offspring that had been the victim. Murphy denied all of the allegations and claimed the newspaper libeled him, ruining his physical and emotional health and damaging his career and reputation as a good man. Ultimately, Murphy won the suit and was awarded a $2.09 million payment. During the trial, when asked what his reaction was to the Carr column, Murphy had said he "wanted to kill him".
Broadcasting Carr has hosted local Boston weekday
radio talk-shows since the 1980s on
WRKO (AM 680).
The Howie Carr Show has since become syndicated on more than twenty-five radio stations throughout northern and central
New England, and can be heard elsewhere via
live streaming on HowieCarrShow.com. In November 2014, Carr left syndicator Entercom Communications and formed his own Howie Carr Radio Network. WRKO had announced it would not carry the show but on March 9, 2015, it became an affiliate on March 16, 2015. In September 2016, the
pay television channel
Newsmax TV began simulcasting
The Howie Carr Show. Carr has filled in for several nationally syndicated talk show hosts, including
Mark Levin and
Dennis Miller. He has also worked as a reporter and commentator for Boston television stations
WGBH-TV and
WLVI.
Literature Carr has written non-fiction books about Boston gangsters, the Kennedy family, and two
novels.
Non-fiction ;Winter Hill Gang series In early 2006, Carr became a book author with the publication of
The New York Times-rated best-seller
The Brothers Bulger, about brothers
Billy and
Whitey Bulger. Whitey was the third boss of the
Winter Hill Gang. Carr's second book,
Hitman, was released in April 2011, two months before Whitey Bulger (then under the name Charlie Gasko) was arrested after sixteen years
on the run. A book about
Johnny Martorano,
Hitman was also rated a best-seller by
The New York Times. In 2013,
Rifleman: The Untold Story of Stevie Flemmi was published. It was followed a year later by
Ratman: The Trial and Conviction of Whitey Bulger. Billy Bulger's power as
President of the Massachusetts Senate intrigued Carr. He began to research both the politician and his gangster brother. Indeed, Carr's arrival on Madison Street in
Somerville, Massachusetts, in the late 1970s meant he was perfectly placed to do just that, for Somerville's Marshall Motors garage (at 12 Marshall Street; now a church) was an early base of the Winter Hill Gang. In 1978, the second leader of the Winter Hill Gang,
Howie Winter, who lived one street away from Carr, on Montrose Street, While Carr believes Whitey Bulger wanted him dead ("his greatest regret is not killing me"), due to his finger-pointing at Billy Bulger, he disputes Kevin Weeks' claim that they were close to killing him by either blowing him up with explosives placed inside a basketball, or by shooting him from a cemetery across the street from Carr's former home at 91 Concord Road in
Acton, Massachusetts. Whitey and Weeks had knowledge of Carr's residence because Carr was a neighbor of one of Weeks' brothers. and Volume II was released in 2018.
Fiction In 2012, Carr moved into fictional writing with his third book,
Hard Knocks, which was followed three years later by
Killers, his sixth and most recent release.
Relationship with Donald Trump During
Donald Trump's
2016 presidential campaign, Carr hosted rallies, and he had lunch with the candidate on his private jet. On June 29, 2016, Carr, as an opening speaker at a rally for Trump in
Bangor, Maine, made a Native American "war whoop" when referring to Democratic Senator
Elizabeth Warren of
Massachusetts. Carr had candidate Trump on his radio show more than a dozen times, including election night. In 2017, Carr and his wife Kathy became members of
The Mar-a-Lago Club, a Trump-owned resort and hotel for dues-paying members. ==Personal life==