Rollins began her legal career as a
law clerk to Judge Frederick Brown of the
Massachusetts Appeals Court from 1997 to 1998. From 1999 to 2002, she was a field attorney for the
National Labor Relations Board and from 2002 to 2006, Rollins was an attorney at
Bingham McCutchen LLP in their
Boston office. Rollins was an
assistant United States attorney for the District of Massachusetts from 2007 to 2011. Rollins served as the general counsel to the
Massachusetts Department of Transportation from 2011 to 2013 and contemporaneously to the
Massachusetts Bay Transportation Authority from 2012 to 2013. She was chief legal counsel to the
Massachusetts Port Authority from 2013 to 2015.
District attorney Election During her campaign, Rollins pledged to
decriminalize certain offenses, such as
shoplifting,
drug possession,
wanton or malicious destruction of property, drug possession with intent to distribute, driving with a suspended or revoked
driver's license, and
resisting arrest. She defeated four other candidates in the September 4, 2018,
Democratic primary and won the November 6, 2018, general election with 80% of the vote against independent challenger Michael P. Maloney. She took office on January 2, 2019.
Tenure Rollins succeeded John P. Pappas, who was appointed by Governor
Charlie Baker to serve as Suffolk County district attorney from September 26, 2018, completing the final months of
Daniel F. Conley's 16-year term. In March 2019, Rollins laid out a
memorandum on resolving
petty crimes without jail time. In her capacity as district attorney, she required prosecutors to visit jails. A study by economists at
Rutgers University,
Texas A&M University, and
New York University found that Rollins's policy change whereby nonviolent misdemeanor offenses would not be prosecuted did not lead to an increase in crime rates and that it reduced the likelihood that nonviolent misdemeanor offenders would be arrested in the future.
Cash bail After campaigning on a platform that included reducing the use of
cash bail, Rollins has since critiqued the
Massachusetts Bail Fund for securing the release of incarcerated people charged with
violent felonies from
pretrial detention. After a person bailed out by the Massachusetts Bail Fund allegedly committed another sexual assault following their release, Rollins became embroiled in a debate over the nature of cash bail, with critics arguing that bail should not be used to keep individuals incarcerated who cannot pay, and community safety should be ensured through other methods. Rollins faced further criticism when her office successfully secured an increase in the bail of a person experiencing homelessness who was charged with armed robbery when learning he would be bailed out by the fund. In September 2021, a committee vote to advance Rollins' nomination was delayed after Cotton wanted more time to convince colleagues to oppose her. On September 30, 2021, her nomination was stalled in committee by an 11–11 vote. On December 8, 2021, Vice President
Kamala Harris cast a tie-breaking vote on the Senate's motion to invoke
cloture on, as well as to confirm, Rollins's nomination. After her confirmation, the
United States Marshals Service refused Rollins' request for a full time security detail, assessing that she was at a low risk of actual harm after receiving death threats via email. On January 10, 2022, she was sworn in as the United States attorney for the District of Massachusetts.
Ethics probe and resignation In November 2022, the
inspector general of the
United States Department of Justice (DOJ) opened a wide-ranging ethics probe into Rollins' appearance at a
Democratic National Committee political fundraiser with First Lady
Jill Biden, her travel, and use of her personal cellphone. The inspector general's 161-page report alleged a broad array of misconduct by Rollins. It accused her of disclosing to a journalist nonpublic information about a possible Justice Department investigation, soliciting and accepting 30 free tickets to a Boston Celtics game and accepting thousands of dollars from a sports and entertainment agency for flights and a stay at a luxury resort. According to the report, Rollins tried to influence the outcome of the race to succeed her as
Suffolk County District Attorney by "repeatedly attempt[ing] to sabotage" the campaign of the rival (
Kevin Hayden) of her favored candidate (
Ricardo Arroyo). The report also found that she had lied under oath to investigators. Another federal watchdog agency, the
U.S. Office of Special Counsel (OSC), found in its own investigative report that on multiple occasions Rollins violated the
Hatch Act, a law that limits political activity by government workers. In a letter to President Joe Biden, Special Counsel
Henry Kerner described Rollins' violations as among the "most egregious transgressions" of the law that the agency has ever investigated: Rollins resigned on May 19, 2023, preventing the federal government from disciplining her.
Post-resignation In February 2024, Rollins was suspended from practicing law in Massachusetts for nonpayment of registration fees. She regained her law license in April. As of March 2024, Rollins was working as the special projects administrator at
Roxbury Community College, reportedly tasked with leading a program for formerly incarcerated people. She was still in that role as of November 2025. In April 2026, Rollins obtained nomination papers (an initial step to qualify for a ballot) for the position of Suffolk County District Attorney, for which the Democratic nominee is due to be selected by a primary election in September 2026—potentially a three-way contest between Rollins, incumbent Kevin Hayden, and former assistant district attorney Linda Champion. == References ==