On bench, Woodlock taps life experiences

Judge shows compassion, toughness

Judge Douglas P. Woodlock has an unwavering devotion to the truth, say those who know him. Judge Douglas P. Woodlock has an unwavering devotion to the truth, say those who know him.
By Andrew Ryan
Globe Staff / January 27, 2011

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He skewered a former state senator earlier this month as “financially embarrassed and fiscally incontinent,’’ and lambasted a former Boston city councilor this week for his “ludicrous’’ testimony.

These admonishments from US District Judge Douglas P. Woodlock were not delivered with shouts of rage. Woodlock spoke in a quiet, plodding cadence from the bench, like an accountant thinking aloud. Along with the blistering rebukes, he delivered substantial prison terms for Dianne Wilkerson and Chuck Turner, cases that have thrust him in the public spotlight.

The superficial profile of the judge would tell the story of a former tabloid news reporter and public-corruption prosecutor who found his way to the federal bench. But interviews with his former law clerks, co-workers, past adversaries in the courtroom, and fellow judges paint a picture of a man with broad life experiences that inform his decision.

Woodlock, who declined to comment yesterday, served as chairman of the state agency that represents indigent defendants and has been known in his 25 years in the judiciary to lash out at prosecutors with the same sharp tongue. He has a habit of visiting some of the convicts he has sentenced in federal prison, one former law clerk said, and has an affinity for architecture and public art.

Above all, Woodlock has an extraordinary devotion to the truth, according to those who know him. He developed that virtue long before he took up the law: Woodlock worked as a newspaper reporter, first interning at the now-defunct Chicago Daily News in summer 1968, when protests over the Democratic National Convention exploded in Grant Park.

He caught on with a tabloid, the Chicago Sun-Times, where the 22-year-old pursued leads with Bob Greene, the former Chicago Tribune columnist who interviewed his friend when they both turned 40.

“When I was starting out as a reporter, I used to go chasing people’s stories,’’ Woodlock told his former co-worker for a 1987 story in Esquire magazine. “The difference now [as a judge] is that people bring their stories to me.’’

From the bench this month, Woodlock made clear his disdain for public corruption, noting at the sentencing of both Wilkerson and Turner that politicians have not gotten the message.

Woodlock sat on a judicial panel that heard a case about the Legislature’s redistricting plan that ultimately led to an obstruction-of-justice conviction for Finneran, whose implausible testimony was highlighted by the judges. This week, Woodlock compared Finneran to Turner, whose testimony he said also bordered on the absurd.

Last June, Woodlock turned his biting wit on federal prosecutors, accusing the US attorney’s office of “overreaching’’ in a case in which an official in the US Department of Homeland Security was charged with a felony for encouraging her Brazilian housekeeper to stay in the country illegally. “This is a cleaning lady,’’ Woodlock told prosecutors several times. “There must be some sense of proportion.’’

Woodlock can often be harder on prosecutors, according to attorneys who appear in his court, because he holds them to a higher standard after his time in the US attorney’s office working on corruption and organized crime.

“He’s well known for challenging prosecutions when there are issues involving defendants’ Constitution rights,’’ said defense attorney Martin G. Weinberg, who has faced Woodlock as a prosecutor and a judge.

US District Court Judge Nancy Gertner described her colleague and longtime friend as a jurist who “has a very diverse background.’’

“I think he brings all of that to bear in his judging,’’ she said.

Born in 1947 in Hartford, Woodlock moved with his parents to La Grange, Ill., a suburb of Chicago. After two years of high school, he came east to attend Phillips Academy in Andover and Yale University, class of 1969.

His newspaper career took him from Chicago to the Illinois state capital and ultimately to Washington, D.C., to cover the US Supreme Court, where he was attracted to the practice of law and enrolled at Georgetown.

Appointed to the federal bench in 1986 by President Reagan, Woodlock has maintained the respect for truth and hard facts that he first chased as a journalist.

“The few times I have seen him disturbed in court was when lawyers, defendants, or witnesses presented evidence or arguments that were false or misleading or intentionally wrong,’’ recalled Boston attorney Thomas A. Reed, who clerked for Woodlock in 1993.

Reed first met Woodlock in 1992 when the judge swore him and several other new lawyers into the federal bar. Almost 20 years later, Reed remembered Woodlock’s advice to the new lawyers.

“It’s crucial in law that you go for the jugular, not the capillaries,’’ Woodlock said, according to Reed. “Too many lawyers spend time on capillary surgery, which they may do perfectly, but it’s perfectly meaningless.’’

But the judge also cracks deadpan jokes from the bench and is a “very warm person as a mentor to his clerks, which may come as a surprise to people who come before him, because he can be tough,’’ said another former clerk, attorney Inga S. Bernstein.

Greene, the former Tribune columnist, dug even deeper. In the Esquire story, his old friend reflected on the power he had over the lives of others.

“The first long sentence I gave was eight years,’’ Woodlock said. “The crime was bank robbery. I’ll admit it to you: I lost sleep before passing sentence, and I lost sleep afterward. It’s a terribly intimidating responsibility to fulfill.’’

Andrew Ryan can be reached at

Correction: Because of a reporting error, an earlier version of this story about US District Judge Douglas P. Woodlock gave the wrong attribution for a quote about former Massachusetts House speakers Thomas M. Finneran and Charles F. Flaherty, who were convicted of federal crimes. It was Assistant US Attorney John T. McNeil, not Woodlock, who said that Finneran and Flaherty had been “welcomed back like they were some sort of heroes” at the State House.

Douglas P. Woodlock
Born: Hartford, 1947.

Education: Yale College and Georgetown Law School.

Career: Reporter, Chicago Sun-Times (1969-73), including a stint covering the US Supreme Court. Office of Chief Counsel for the Division of Corporation Finance at the US Securities and Exchange Commission (1973-75). Clerk to US District Judge Frank J. Murray in Boston (1975-76). Private practice with Boston firm of Goodwin, Procter & Hoar (1976-79 and 1983-86). Assistant US attorney in Boston prosecuting political corruption and organized crime cases (1979-83.) Appointed US district judge by President Reagan (1986).