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He’s a motorcycle-riding, plain-speaking advocate who has spent decades representing some of the most notorious criminal defendants in Massachusetts history, and is now embattled in what could be a legacy-defining case.
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Kevin Reddington, the lawyer for Lindsay Clancy, has struck a chord with online and television trial viewers across the nation as he has tried to convince a Massachusetts jury that his client was effectively insane when she fatally strangled her three small children on a January 2023 evening.
Reddington has showcased a talent for keeping complex psychological testimony simple, and humanized his client even when he’s saying nothing at all. He has sauntered around the courtroom while asking witnesses plainly worded questions, and gripped Clancy’s hand during graphic testimony about how she killed her children.
Whether it’s at the front of his mind or not, Reddington, 75, is also navigating the contemporary court of public opinion: a social media landscape that might have been unimaginable early in his career. He represented such figures as former Boston Red Sox star Mo Vaughn in a 1998 drunk driving case and the longtime girlfriend of Boston mobster James “Whitey” Bulger, Catherine Greig, who pleaded guilty to harboring a fugitive in 2012.
But the seasoned attorney has negotiated that virtual landscape with ease during Clancy’s trial, inspiring memes on TikTok and Instagram that have helped rally support for his client.
Now, as the jury nears its deliberations in the divisive case, Reddington’s skills and decades of experience will be put to the ultimate test.
It’s that track record of experience that makes him the best kind of advocate for Clancy, according to Martin Weinberg, a prominent Boston criminal defense lawyer who was an appellate lawyer for another famous criminal defendant, Karen Read. Read was accused, and acquitted in 2025, of killing her boyfriend, Boston police officer John O’Keefe.
“She wisely selected a lawyer that’s comfortable with mental-condition defenses, is comfortable trying homicide cases, and has the experience to maximize her chances to succeed,” Weinberg told USA TODAY.
“It’s just like it would be if you were a medical patient going in for some unusual or challenging surgery. You’d want a doctor that’s done it, and not a doctor who’s doing his first operation on the kind of medical condition you have,” Weinberg said.
For a lawyer, Reddington cuts an atypical figure when he’s outside the courtroom. An NBC Boston 10 news report shows a photo of the wizened lawyer in a sleeveless denim-and-leather outfit with an exposed arm tattoo, sitting atop his Harley motorcycle. He told the outlet ahead of the Clancy trial that he handles about 10 trials a year and isn’t planning to retire soon.
“I don’t want to work at Walmart, I don’t want to work at Lowes, you know. So I think I like what I’m doing, I enjoy what I’m doing,” Reddington said.
History with major cases, insanity defense
If Reddington is able to persuade jurors that Clancy, who is paralyzed from what Reddington says was a suicide attempt, was temporarily insane when she killed members of her household, it wouldn’t be his first time pulling off that feat.
Reddington shot to prominence nationally more than 35 years ago when he won an acquittal for Massachusetts resident Therese Rogers by arguing that she was insane when she fatally stabbed her boyfriend in the eyes while he slept. Rogers was rendered delusional by post-traumatic stress disorder and battered woman syndrome after years of suffering her boyfriend’s abuse, Reddington told jurors.
That win earned him an invitation to the American College of Trial Lawyers, an invitation-only group that caps its membership at less than 1% of the total lawyer population of any state.
Reddington’s stardom increased when he won an acquittal in 1998 for Vaughn, the former Boston Red Sox slugger who was accused of driving drunk when he got into a crash after leaving a night club. Reddington argued that Vaughn’s poor performance on field sobriety tests after refusing a breathalyzer was caused by the crash itself.
True to the life of a much-sought-after criminal lawyer, Reddington has also represented prominent clients who weren’t able to beat the charges against them.
After Greig, who was a longtime girlfriend of Boston mobster James “Whitey” Bulger, pleaded guilty in 2012 to harboring Bulger when he was a fugitive, Reddington asked a judge to send her to prison for 27 months, saying she acted out of love. Greig received an eight-year sentence – near the prosecution’s desired 10-year sentence – all the same.
Reddington mounted another insanity defense when he represented Michael “Mucko” McDermott, who killed seven co-workers in 2000. McDermott testified that he believed he was actually killing Adolf Hitler and Nazi generals to stop the Holocaust, telling the police who arrested him, “I don’t speak German.” Reddington said his client suffered from schizophrenia and was in psychosis during the killings, but a jury found McDermott guilty after deliberating across three days.
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Weinberg praised Clancy’s “sagacity to hire somebody with Kevin’s experience and comfort level in these kinds of homicide trials.”
“Kevin’s tried dozens, if not hundreds, of major felonies,” he said.
‘Tell her we love her’
In criminal trials, prosecutors often seem to exhibit the most humanity in the courtroom, giving voice to victims who may be dead or gravely harmed, while defense lawyers may try to undercut that picture.
In Clancy’s case, however, Reddington has won more vocal sympathy in major news and viewing platforms than his adversary.
When Susan Clancy, Lindsay Clancy’s former mother-in-law, was called by Reddington to the stand to describe the loss of her three grandchildren, and her observations of her daughter-in-law’s psychological suffering in the months leading up to the killings, prosecutor Shanan Buckingham shocked observers by implying that she would be a bad Catholic if she didn’t condemn her deceased grandchildren’s mother.
Buckingham asked Susan Clancy to confirm she’s an active member of the Catholic Church. When she did so, Buckingham responded: “So you’re aware that murder is considered a mortal sin?”
Multiple in-person observers said there was an audible gasp in the courtroom, before the judge called the lawyers to his bench and then instructed the jurors to ignore the prosecutor’s question. Several legal commentators suggested that the query could even have been grounds for a mistrial.
Reddington, by contrast, has struck a chord with some onlookers as he has attempted to convince the jury that the victims in the case were precious, and were killed by a mother who loved them deeply.
“In this case, God bless you. You people are gonna have to listen to some of the most horrific things, look at some of the most horrific things,” Reddington told jurors in his opening statement.
“She’s living her own hell. She knows what happened with those kids,” he said of Clancy.
Reddington has also solicited testimony from a plethora of witnesses – family members, friends, and medical providers who knew Lindsay Clancy or knew her children – that she was a very good mother before she killed her children.
In his opening statement, Reddington described the trial as “a referendum on women’s having babies and having postpartum psychosis, postpartum depression.”
As the prosecution walked jurors through hours of painstaking testimony about the nature of the children’s deaths, the injuries they suffered, the clothes they were wearing, and how the smallest child, Callan Clancy, survived for another three days, Reddington was often squeezing the hand of his visibly tearful, shaking client.
“Tell her we love her,” one supporter told Reddington days later outside the courthouse.
“I will,” he replied.
That was just one of the many supporters of Lindsay Clancy who have rallied outside the courthouse and cheered on Reddington as the trial has unfolded.
Reddington has also garnered fans online, with memes and content-creator videos featuring his plain-talking style, the poster boards he has presented to jurors to enlarge evidence supporting the defense, and his frustrated and impatient expressions as he has watched prosecutors present their case.
“I have no words. It’s amazing,” Reddington told one reporter, when asked what he thought of the support.
This article originally appeared on USA TODAY: ‘It’s amazing’: Lindsay Clancy’s defense lawyer has shot to stardom
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Reporting by Aysha Bagchi, USA TODAY / USA TODAY
USA TODAY Network via Reuters Connect
Copyright Reuters or USA Today Network via Reuters Connect