Connecticut Gov. John G. Rowland, right, swears Judge Francis M. McDonald in as Chief Justice of the Connecticut State Supreme Court in 1999. Connecticut Gov. John G. Rowland, right, swears in Judge Francis M. McDonald as chief justice of the Connecticut Supreme Court in 1999. Photo: Bob Child/AP

Known in the state’s legal circles as an outspoken, witty and compassionate jurist who tilted right but had a libertarian streak, former Connecticut Chief Justice Francis McDonald died Oct. 8 in Waterbury. He was 87 years old and passed away due to complications from pneumonia.

A former FBI agent, prosecutor and Superior Court judge, McDonald joined the state’s high court as associate justice in 1996. He became chief justice in September 1999 and stayed in that post until January 2001, when he reached the mandatory retirement age for judges of 70.

Although he was on the Supreme Court for less than five years, including 16 months as chief justice, the Waterbury native and Yale graduate was never a sure vote for either side of the political aisle, many said. Although he was considered a conservative, he often sided with Justice Robert Berdon, then the court”s most liberal justice.

“I considered him a more libertarian type, but it was often the case where McDonald and Berdon were the court’s two dissenters,” said Wesley Horton, a partner with Hartford’s Horton, Dowd, Bartschi & Levesque. Horton, who has appeared before the state’s high court about 130 times, including about 20 in front of McDonald, said of McDonald and Berdon: “There you had the right wing of the court meet the left wing of the court and be opposed to where the center of the court was.”

One example of McDonald’s libertarian streak was his dissent in the 2000 ruling of Seymour v. State Elections Enforcement Commission, said William Dunlap, a professor of law at Quinnipiac University School of Law.

“He had a reputation as a frequent dissenter and a libertarian. Seymour was one dissent, particularly, where those two merged,” said Dunlap, who also teaches constitutional and criminal law. McDonald, along with Justice William Sullivan, who would succeed McDonald as chief justice, were in the 3-2 dissent, which McDonald wrote.

The Seymour case involved a candidate for local office who did not have big campaign coffers, who wrote a press release on her computer and faxed it to a local newspaper. Election laws at the time required that any time any money was spent on that type of publicity, the publicity had to have the phrase “paid for by” and the name of whomever financed it. The commission held that the candidate violated the law and that was upheld by the state Supreme Court.

“He issued a passionate First Amendment defense arguing that the law simply should not apply to people who engage in this kind of campaigning from their homes. He wanted to prevent the government and established political parties from making it more difficult for individuals to break into the political system,” Dunlap said Friday.

Horton, who authored “The History of the Connecticut Supreme Court,” said McDonald “was interesting as a justice in oral arguments. His questions were unpredictable. You could prepare and prepare and prepare, but he’d come up with a question you just had not thought of and that happened time and time again.”

The unpredictability was echoed by Patrick Tomasiewicz, a partner with Hartford’s Fazzano & Tomasiewicz, who knew McDonald off the bench.

“He was a fun, smart, witty and an unpredictable judge,” said Tomasiewicz, who is also an adjunct paralegal studies professor at the University of Hartford. “I agree he was somewhat a libertarian. He was also a man who had great respect for his position as judge and who wore the robe with honor and dignity.”

Tomasiewicz recalled one time that McDonald, then a Superior Court judge, almost found him in contempt.

“The case was about prejudgment remedy in a real estate matter and he ruled in my favor,” Tomasiewicz said Friday. “During the hearing, I was advocating for a position quite forcefully, and I think I got a little bit out of line,” he said. Tomasiewicz was told to approach the bench, where McDonald asked, “Do you want to go to the can?”

“I said absolutely not. He then told me to tone it down, and I did just that,” Tomasiewicz said.

While McDonald was known as an outspoken, strong and sometimes complicated jurist, those who knew him said you definitely knew he was a New Englander. ”He went to Yale and was a Yankee through and through,” Tomasiewicz added. “He also had a wonderful and wry sense of humor.”