He favors khaki pants and oxford shirts, graduated summa cum laude from college and proposed to his fiancée on a Maine beach. But Philip Markoff, a tall, blond medical student, also is a brutal predator, prosecutors said Tuesday.

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BOSTON — He favors khaki pants and oxford shirts, graduated summa cum laude from college and proposed to his fiancée on a Maine beach. But Philip Markoff, a tall, blond medical student, also is a brutal predator, prosecutors said Tuesday.

“Philip Markoff is a man who is willing to take advantage of women, to hurt them, to beat them, to rob them,” Suffolk County District Attorney Daniel Conley said after Markoff, 22, pleaded not guilty in Boston Municipal Court. “He thought he was going to get away with it; he thought he was too smart for us.”

But if Markoff did kill Julissa Brisman, a masseuse and aspiring model with whom he supposedly arranged an appointment through Craigslist early last week, he did a poor job of covering his tracks.

Conley said investigators found a semi-automatic handgun, ammunition, duct tape and plastic zip ties at Markoff’s apartment in Quincy, south of Boston, while executing a search warrant late Monday. The plastic ties were the same kind used to bind the hands of Brisman on April 14, Conley said, and of a second masseuse whom Markoff is charged with robbing at gunpoint on April 10.

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Friends described Markoff as an industrious student who always had excelled, but who also had a weakness for gambling and hanging out in bars.

Markoff was on his way to Foxwoods Resort Casino in Connecticut with his fiancée and $1,000 in cash when he was arrested. James Kehoe, who said he was close with Markoff at SUNY Albany, said Markoff had played a lot of poker at school, wagering money on games with other students.

“He did used to play a lot, into the late hours,” Kehoe said. “He got into debt with the games and kept trying to win it back.”

Both attacks took place at hotels in Boston’s expensive Back Bay neighborhood, a popular destination for tourists and business travelers. And security cameras captured a tall, blond man leaving both hotels shortly after the attacks took place, peering coolly at his cellphone as he strode out.

Police used records from that cellphone account to quickly track down Markoff, as well as an IP address that led them to his Quincy home.

“They begin to put the house under surveillance,” Conley said. “They see Philip Markoff, he matches the description quite remarkably, and again the case just begins to build from that point.”

ABC News reported Tuesday night that Markoff frequented Foxwoods and gambled there two days after Brisman’s death, leaving with $5,300 in winnings.

But law-enforcement officials refused to say whether a gambling problem might have motivated Markoff to trawl Craigslist for women to rob.

Markoff’s lawyer, John Salsberg, said he was “not aware of any gambling problem” and suggested that police had the wrong man.

In the hours before the court proceeding, Markoff’s fiancée, Megan McAllister, reached out to several television networks to proclaim his innocence. According to ABC’s “Good Morning America,” McAllister sent the show an e-mail describing Markoff as “a beautiful person inside and out” who “could not hurt a fly.”

Markoff’s father is a dentist in Syracuse, N.Y.; he did not respond to requests for comment Tuesday. Nobody answered the phone at the home of Markoff’s mother, Susan Carroll, in Oneida, N.Y., outside Syracuse.

Several professors at SUNY Albany, from which Markoff graduated in 2007 with a degree in biology, said he had received A’s in their classes.

“Since I don’t give many A’s, he was obviously an excellent student,” said Frank Hauser, an emeritus professor of chemistry who said he had taught Markoff’s organic chemistry class in the spring of 2006. “I think it’s really unfortunate that someone that bright would be in this much trouble.”

While Markoff liked to party, played a lot of video games and occasionally smoked marijuana, according to Kehoe, he was “pretty driven” to succeed in the same way his father had.

“He kept plowing through it,” Kehoe said, referring to Markoff’s schoolwork. “He was driven to follow in his dad’s footsteps.”

According to prosecutors, Markoff’s main motive was to rob Brisman in her room at the Boston Marriott Copley Place. He fired three shots at Brisman, they said, and one passed through her heart, killing her. He also hit her on the head, they said.

“The evidence we have suggests that Julissa put up a pretty tough struggle,” Conley said, “and it was in the context of that struggle that she lost her life.”

Brisman was pronounced dead that night at Boston Medical Center — the teaching hospital where Markoff had been learning how to save lives.

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