A Boston lawyer accused of rape by as many as a dozen women has avoided conviction since 1996. Now, prosecutors are trying a different tack.

Juries twice have acquitted Gary Zerola of rape.Dina Rudick/Globe Staff

The accusations, time and again, involve a Donald Draper-handsome lawyer, his date, and her young girlfriend (whom he has met at least once before).

After multiple drinks at a Boston bar, where the former prosecutor turned defense attorney pays the hefty tab, the three relocate to a local apartment, oftentimes his. There the festivities fade to booze-drenched slumber.

The predawn hours inevitably shatter as the young friend awakens and realizes she has been undressed and is being raped by the man who so generously spirited the party along.

Over the years, as many as a dozen women have come forward to allege Gary Zerola raped them in nearly indistinguishable assaults dating back to 1996, court records show.

Despite the numerous accusations, the 50-year-old with a law office on Beacon Hill has rarely faced criminal charges, much less a conviction. Juries twice have acquitted Zerola of rape. He has had sex charges dropped in Miami Beach and New Orleans and seen statutes of limitations run out on at least three allegations from the 1990s, court filings show.

Boston attorney Gary Zerola embraced friends in Superior Court in Boston after being acquitted for the second time in 2008 of charges related to sexual assault. Ted Fitzgerald

Now, prosecutors are taking a new tack, by seeking to join two cases.

Indictments from 2017 and this year accuse Zerola of raping women, ages 21 and 23, in assaults prosecutors describe in court papers as “uncannily similar.”

In the motion to join the cases, scheduled to be heard Monday in Suffolk Superior Court, prosecutors argued that “similar other conduct by Zerola spanning the last 25 years reinforces the appropriateness” of the strategy.

Zerola, who in 2001 was named a “most-eligible bachelor” by People magazine, has pleaded not guilty to two counts of rape, one count of aggravated rape, and a count of breaking and entering for allegedly returning to a passed-out victim’s Boston apartment without permission. His defense lawyer has filed a counter motion to keep the two current cases separate. That motion has been impounded from public view.

Zerola is under house arrest in Salem. Under court order, he is prohibited from having any female visitors — relatives and lawyers excluded — without clearance from probation.

Zerola did not return a message to his answering service seeking comment. Neither did Zerola’s defense lawyer, Joseph F. Krowski Jr.

Zerola’s foster mother declined to comment when reached by telephone.

Prosecutors want Judge Christine M. Roach to consider allegations against Zerola from 1996, 1997, 1999, and 2006 in analyzing whether “the 2017 and 2021 indictments represent parts of a common pattern and an intention to victimize younger women rendered vulnerable by alcohol.”

According to prosecutors, the evidence is “strong.”

“It was not mere happenstance that Zerola targeted women more than 20 years his junior, who had correspondingly lesser experience in social settings, especially those fueled by alcohol,” prosecutors wrote.

The Boston Globe also found in court records a footnote citing four additional alleged rapes that “lack the same substantial similarities,” as well as evidence of dropped cocaine and sexual assault charges from a Jan. 8, 2012, incident in New Orleans.

In a Suffolk Superior Court memorandum from March 17, Judge Janet L. Sanders suggested that Zerola’s experience as a lawyer has benefitted him as a defendant. Zerola, a Suffolk University law graduate, went into private practice after brief stints as a prosecutor in Essex and Suffolk counties two decades ago.

“That the defendant is an attorney (and former prosecutor) also means that he is well aware of the law, and as the Commonwealth suggests is fully capable of laying the groundwork for a consent defense before engaging in the acts he’s accused of,” Sanders wrote.

Around the time People magazine declared Zerola one of its most eligible bachelors two decades ago, he also spearheaded a nonprofit for children growing up without their birth parents.

The charity, One for the Kids, dissolved in 2005 but not before then-Mayor Thomas M. Menino presented Zerola with a $30,000 Boston Neighborhood Fellows Award for his advocacy on behalf of foster children, according to a Boston Magazine article published in March 2008.

The magazine profile, written two months after Zerola’s first acquittal in January 2008, described his trial testimony as free, open, and charismatic as he spoke of lavish spending, routinely picking up bar tabs, being a nightclub gadabout, and dating younger women.

In juxtaposition, the alleged victim, a 19-year-old University of Massachusetts Amherst student, came across as “contradictory and occasionally giggling,” the article said.

Zerola melted into sobs when the jury, after two days of deliberations, returned a not-guilty verdict, the article said. Key to the acquittal was the exclusion of evidence of other similar acts, it said.

A photo at zerolalaw.com captures Zerola in profile — square jawed, arms crossed, chin resting in the crook of his left thumb and index finger. His law office is listed as 11 Beacon St., one block from the State House.

Online client testimonials praise Zerola’s preparedness and legal acumen: “He is a beast when it comes to criminal defense,” one reads.

“Gary Zerola will give you an unprecedented level of attention, care and legal savvy,” another one says.

Zerola’s law license is active. He experienced a temporary suspension Nov. 1, 2007, but was reinstated by April 3, 2008, according to the Massachusetts Board of Bar Overseers.

In Zerola’s two current cases, prosecutors say that partying in the North End shifted to an apartment, where more drinking gave way to drunken sleep.

On Nov. 9, 2016, Zerola, a woman he was dating, her girlfriend, and another lawyer relocated to the lawyer’s Beacon Hill apartment.

When the party died down, the 23-year-old girlfriend fell asleep on a sectional couch. Zerola and his date slept on another part of the couch.

The girlfriend awoke to Zerola, then 45, raping her, according to criminal court filings.

On Jan. 12 this year, the alleged victim was so intoxicated she vomited in Zerola’s car while on the way home with Zerola and his date, according to court filings. Once at the woman’s Boston apartment, Zerola’s date put her to bed and left with Zerola.

Zerola, then 49, is accused of returning to the drunk woman’s apartment and raping her while she was passed out. The 21-year-old victim awoke to find Zerola “sexually assaulting her,” court records show. Zerola claimed the victim had given him her key and asked him to return to her apartment, according to the records.

In several alleged rapes, victims recalled another distinguishing factor as they were jolted awake.

Each time, they said, Zerola quipped: “Don’t you want to play?”

Correction: An earlier version of this story incorrectly described Zerola’s parents.