Mark L. Wolf

From 1901 until 1947, the city of Boston, Massachusetts, sponsored public celebrations of St. Patrick's Day and Evacuation Day, which marks the departure of British troops from the city in 1776. In 1947, Mayor James Michael Curley gave authority for organizing the parade over to the South Boston Allied War Veterans Council, a group of unincorporated private citizens selected from a variety of Boston veterans' groups – the only group to apply for a permit until 1992. That year, the Irish-American Gay, Lesbian and Bisexual Group of Boston (GLIB) requested that it be allowed to march in the parade alongside the usual participating groups. GLIB argued that it was not a group primarily aimed at conveying a "gay, lesbian, and bisexual message." In 1995, Judge Wolf ruled that the South Boston Allied War Veterans Council could prohibit participation by those who endorsed that political stance as an exercise of the organizers' free speech under the First Amendment, and encouraged GLIB to organize its own parade.[11] He ordered the city of Boston to issue the parade permit, which it had been threatening to withhold, to South Boston Allied War Veterans Council. In a related case, The Supreme Court of the United States unanimously agreed with Wolf's decision in a landmark judgement on free speech, specifically the right of groups to determine what message their activities convey to the public. The Court ruled in Hurley v. Irish-American Gay, Lesbian, and Bisexual Group of Boston that private organizations, even if they had permits for a public demonstration, may exclude groups if those groups presented a message contrary to the one the organizing group wanted to convey.[12]

Judge Wolf's judicial work exposed corruption in the Federal Bureau of Investigation's handling of matters involving notorious criminals James “Whitey” Bulger and Stephen Flemmi. In 1998, Wolf ordered the FBI to divulge that Bulger and Flemmi were top echelon FBI informants. Following nine months of hearings, Wolf issued a 661-page decision finding that the FBI had not investigated Bulger and Flemmi for serious crimes, including murder; it had warned Bulger and Flemmi when other federal agencies were investigating them; it told Bulger and Flemmi of informants against them who were, as a result, killed; and it told Bulger and Flemmi that they were about to be charged so they could flee, which Bulger did.[13] Although Flemmi had not been granted immunity from FBI prosecution, Wolf decided that the information he had provided could not be used against him. The ruling was reversed by the Court of Appeals, but the defendants, except Bulger who was a fugitive, eventually pled guilty. Several years later, investigators found a grave in Boston with the bodies of three of Bulger’s victims. Bulger was finally apprehended in 2011, convicted, and sentenced to serve life in prison, where he was murdered. In an editorial, The New York Times credited "Judge Wolf's courage and persistence" in the case.[14] Since then, the government has paid out more than $100 million in claims to the families of people murdered by informants shielded by the FBI, an FBI agent was later sentenced to 50 years in prison, and there were Congressional hearings into the FBI's use of murderers as informants.

In July 2001, Gary Lee Sampson carjacked and murdered two people: Philip McCloskey (aged 69 of Taunton, Massachusetts), Jonathan Rizzo (aged 19 of Kingston, Massachusetts), and later killed a third, Robert Whitney (aged 58 of Concord, New Hampshire). The murders of McCloskey and Rizzo were federal offenses. Sampson pled guilty. Wolf acknowledged that "Sampson's motion to dismiss present[ed] a serious question whether the Federal Death Penalty Act (FDPA) is unconstitutional because of the mounting evidence that innocent individuals have been sentenced to death, and undoubtedly executed, more often than previously understood."[15] Nevertheless, Wolf held that declaring the FDPA unconstitutional was not legally justified. In sentencing Sampson to life in prison, Wolf said:  "You personify the wisdom of [the poet Auden who wrote] “Evil is unspectacular and always human … And shares our bed and eats at our own table.”" He later added that "By committing horrific crimes that virtually compelled decent people in this community to condemn you to die, you have diminished, if not degraded, us all."[16] After discovering that a juror had lied to be selected to serve, Judge Wolf vacated Sampson's sentence and ordered a new trial.

In 2007, Judge Wolf ruled that religiously motivated parents do not have a constitutional right to exempt their elementary school children from teaching on homosexuality and same-sex marriage, finding that there was no evidence of extreme indoctrination that might constitute a form of coercion.[17] In his opinion he wrote that "public schools are entitled to teach anything that… helps students become engaged in democracy… reduces future discrimination… teaches young children to understand and respect others… [and] makes homosexual students feel more comfortable."

In 2009, Salvatore DiMasi, the former speaker of the Massachusetts House of Representatives, and three others were charged with conspiracy, honest services fraud, mail fraud, and wire fraud. Federal prosecutors later added an extortion charge against DiMasi.  DiMasi was convicted after a seven-week trial. Wolf sentenced him to serve eight years in prison for extortion and honest services fraud.[18] At the time, Wolf said he hoped that DiMasi's sentence would put a stop to Beacon Hill, Boston’s "culture of arrogance."[19]

Michelle Kosilek, a pre-operative transsexual who had been convicted of murdering her partner, sued the Massachusetts Department of Corrections (DOC), arguing that its refusal to provide sex reassignment surgery constituted "cruel and unusual punishment" under the Eighth Amendment to the United States Constitution. In September 2012, Judge Wolf ordered the DOC to provide Kosilek with sex reassignment surgery, which the DOC's medical personnel determined was medically necessary as a treatment for Kosilek's gender dysphoria. In 2006, The Boston Globe had opposed Kosilek's surgery because "private insurers rarely pay for sex-change operations" and "hormone treatment and expert therapy" are "sufficient". However, in 2012, The Boston Globe wrote that Wolf's decision made a persuasive case that the surgery was "medically necessary, not an elective procedure," however "distasteful."[20][21] In his ruling, Wolf found that "Michelle Kosilek, who lives as a woman in a male prison facility, had experienced "intense mental anguish," and said there was a serious medical need" for her to have the procedure.[22] Wolf’s decision was initially affirmed[23] but ultimately reversed on appeal.[24]

In 2018, five undocumented immigrants and their spouses filed a lawsuit against the US government alleging that they were unlawfully arrested and detained by U.S. Immigration and Customs Enforcement (ICE).[25] Some were detained after interviews, at which they demonstrated that they were truly married. Wolf rejected the government's argument that the case should be dismissed, repeatedly finding that ICE was illegally detaining the aliens pending resolution of their immigration case.[26]