Overview[1]

George O’Toole Jr. was born on October 7, 1947 in Worcester, Massachusetts. He earned an AB degree from Boston College in 1969, and a Juris Doctor degree from Harvard Law School in 1972.

After completing his formal legal education, O’Toole worked as a private-practice attorney in Massachusetts from 1972 to 1982 before serving as an associate justice in the Boston Municipal Court from 1982 to 1990.

In 1990, Massachusetts Governor Michael Dukakis, a Democrat, appointed O’Toole as an associate justice for the Superior Court of Massachusetts, where he would go on to serve until 1995.

O’Toole’s move toward the federal judiciary began on April 4, 1995, when President Bill Clinton – acting on the recommendation of Democrat Senators John Kerry and Ted Kennedy – nominated him to the U.S. District Court for the District of Massachusetts. The United States Senate subsequently confirmed O’Toole with a voice vote on May 25, 1995, and he received his commission the following day. O’Toole went on to serve as a district court judge for 23 years before assuming senior status on January 1, 2018 – a status he continues to hold.

The Case of Exams for Police Officer Promotions

One of the more high-profile cases over which Judge O’Toole has presided during his career was a 2011 lawsuit — Tatum et al. v. Commonwealth of Massachusetts — in which the plaintiffs, a group of nonwhite police officers in Boston, alleged that the Massachusetts civil-service exam for police promotions had resulted in a negative “disparate impact” on black and Hispanic candidates who took the test between 2005-2008. In other words, members of those demographic groups had failed the exam at significantly higher rates than their white counterparts. Thus, said the plaintiffs, the test itself was in violation of Title VII of the 1964 Civil Rights Act.

When O’Toole rendered his verdict on this case in September 2014, he concluded that while the promotion exams for Boston police did in fact have a “significant adverse impact” on nonwhite candidates, the City was correct in its contention that the questions on the test were sufficiently “job-related” to be regarded as valid measures of the candidates’ essential knowledge regarding police-department rules and regulations. O’Toole was further persuaded to rule that the overall testing process was legitimate, by the fact that the written, multiple-choice exam was supplemented by a rating system designed to evaluate intangible abilities like leadership and interpersonal skills. And when the plaintiffs suggested that the written exams should be eliminated completely and replaced by oral interviews, they were unable to persuade O’Toole that such a change would have resulted in a lesser adverse impact on nonwhite minorities. Thus, the case ended with O’Toole ruling that police departments in Massachusetts would not be required to change their testing procedures based on the specific facts of the Tatum et al. v. Commonwealth of Massachusetts case.

The Case of the Boston Marathon Bomber[2]

Yet another prominent case over which Judge O’Toole presided was the legal prosecution of Dzhokhar Tsarnaev, who was accused of helping to orchestrate the detonation of two pressure-cooker bombs near the finish line of the 117th Boston Marathon on April 15, 2013 — explosions that killed 3 people and wounded more than 260 in the densely packed crowd of onlookers. Tsarnaev was charged with 30 criminal counts, 17 of which were potentially punishable with the death penalty under federal terrorism laws.

While O’Toole denied a request by Tsarnaev’s attorneys for unfettered access to the prosecution’s files in the case against their client, the judge agreed to let them access such things as recordings of calls that Tsarnaev had made while in custody after the bombings, and information regarding Tsarnaev’s eligibility for capital punishment.

On February 20, 2014, Judge O’Toole approved the Tsarnaev defense attorneys’ request for permission to add a second death-penalty expert to their legal team, By O’Toole’s telling, the attorneys had made a “satisfactory showing” as to why such an additional expert was “necessary for adequate representation.”

At a hearing on April 16, 2014, Judge O’Toole ruled that Tsarnaev could be permitted to receive prison visits from his family members without the presence of an FBI agent to monitor their conversations. Rejecting prosecutors’ claims that the presence of such an agent was necessary for security purposes, O’Toole determined that the role of a monitor could instead be fulfilled by an impartial agent not involved in the case.

When Tsarnaev in 2014 requested that certain evidence be kept from the jury during trial, and that the charges against him to be dropped on grounds that the jury-selection process had been unfair to him, O’Toole denied both requests.

In 2015 Tsarnaev was found guilty of all 30 federal counts against him, and the jury sentenced him to execution on six of the charges. The defendant was formally sentenced by Judge O’Toole on June 24.

Blocking President Trump’s Effort to Cut the Federal Workforce & Slash the Federal Budget

On January 28, 2025, the Trump administration, in an effort to significantly reduce the size of the federal U.S. workforce, initiated a “deferred resignation” program — dubbed “Fork in the Road” — giving unionized federal employees an opportunity to voluntarily resign from their jobs in exchange for an enticing financial package. Specifically, all resignees would continue to receive their full salary and benefits — while not working — for the ensuing several months until their official separation date of September 30, 2025. The Trump plan also offered eligible employees an opportunity to retire early in conjunction with deferred resignation.

In response to President Trump’s deferred resignation initiative, labor unions representing federal workers — including the American Federation of Government Employees, the AFSCME, and the National Association of Government Employees – filed suit in early February 2025, claiming that the Trump administration’s offer: (a) was “arbitrary and capricious”; (b) violated the Administrative Procedure Act; and (c) exceeded the Office of Personnel Management’s legal authority. Moreover, as the Federal News Network explained: “In their lawsuit, the unions argue that the government cannot legally promise to pay employees who accept the deferred resignation offer through the end of September, partly because Congress has not yet appropriated funding for any federal agencies beyond March 14. In general, the Antideficiency Act bars federal agencies from obligating funds that Congress has not yet appropriated.”

Even after approximately 65,000 federal workers had quickly elected to take advantage of Trump’s deferred resignation option, Judge O’Toole on February 6 issued a Temporary Restraining Order (TRO) to stay (pause) the original deadline of 11:59 p.m. on February 6 — by which time workers were expected to have indicated whether or not they wished to resign under the terms of the program. He simultaneously set a new deadline of February 10.

Then, after hearing oral arguments pertaining to the case, O’Toole on February 10 further extended the shelf-life of his TRO by blocking the deferred resignation deadline indefinitely, so as to give himself ample time to: (a) carefully weigh the merits of the legal challenges pesented by the federal labor unions, and (b) determine whether or not it would be appropriate to convert the TRO into a permanent injunction.

But on February 12 the judge reversed course and dissolved his TRO. He also terminated the provision of any further injunctive relief to the union plaintiffs, which, he now conceded, lacked the legal standing necessary to justify the implementation of a restraining order. According to Caselaw.com: “The [deferred resignation] program subsequently closed on February 12, and resignations after 7:20 p.m. on that day were no longer accepted.” Any affected employees, said O’Toole, should pursue remedies in administrative venues like the Merit Systems Protection Board before seeking relief in federal court. “The plaintiffs here are not directly impacted by the directive,” the judge stated in his written opinion. “Instead, they allege that the directive subjects them to upstream effects including a diversion of resources to answer members’ questions about the directive, a potential loss of membership, and possible reputational harm. The unions do not have the required direct stake in the Fork Directive, but are challenging a policy that affects others, specifically executive branch employees. This is not sufficient.”

With the announcement of O’Toole’s February 12 ruling, the Office of Personnel Management closed the deferred resignation option to any new applicants, and “Fork in the Road” proceeded to its September 30 conclusion as originally intended by the Trump administration.

Seeking to Place a “Transgender Woman” Convict in a Women’s Prison

During the first week of his second term in office, President Trump issued an Executive Order titled “Defending Women From Gender Ideology Extremism and Restoring Biological Truth to the Federal Government,” which, in a reversal of Biden administration policy, sought to house biological male prison inmates who identified as women, in men’s facilities. Deriding what it characterized as the pretensions of radical “gender ideology” and its notion “that there is a vast spectrum of genders that are disconnected from one’s sex,” Trump’s Executive Order also stipulated that there should be “no Federal funds expended for any medical procedure, treatment, or drug for the purpose of conforming an inmate’s appearance to that of the opposite sex” – i.e., so-called “gender-affirming care.”

On January 26, 2025, Judge O’Toole issued a TRO that blocked federal officials from transferring a self-declared “transgender woman” inmate identified by the pseudonym “Maria Moe,” to a men’s prison after that individual had filed a lawsuit in the U.S. District Court for the District of Massachusetts challenging President Trump’s “arbitrary and capricious” Executive Order. Represented by the National Center for Lesbian Rights, G.L.B.T.Q. Advocates and Defenders, and the law firm of Lowenstein Sandler, plaintiff Moe filed his suit after the Bureau of Prisons had begun taking steps to transfer him to a men’s prison and cut off his access to hormone therapy. Said a January 27, 2025 New York Times report: “The filing alleges that the [Trump] administration failed to comply with federal laws governing how such regulations must be adopted. And it argues that the order violates prisoners’ rights of equal protection under the Fifth Amendment’s due process clause.” The Times piece also said that Trump’s Executive Order, by raising the specter of Moe being denied access to hormones, likewise violated “the Eighth Amendment’s prohibition of cruel and unusual punishment.” Moreover, Moe’s lawsuit alleged that the provisions of Trump’s order were, as the The New York Times put it, “motivated by animus toward transgender people, which makes [those provisions] constitutionally suspect under Supreme Court precedents.”

Footnotes:

1. https://www.fjc.gov/history/judges/otoole-george-jr
   https://ballotpedia.org/George_O%27Toole
2. https://ballotpedia.org/George_O%27Toole