Connecticut Superior Court Judge Leo V. Diana is widely regarded as one of Connecticut’s most conscientious and respected family court jurists. A former mayor turned judge, Diana has built a reputation for fairness, compassion, and an unwavering focus on the best interests of children. Colleagues and court reform advocates alike have praised his dedication and integrity on the bench.
As the state’s Chief Administrative Judge for family matters, Diana has not only presided over complex cases but also led reforms to enhance the court system’s service to families. His career reflects a deep commitment to ensuring that the family court system remains true to its mission: putting children first.
A Career Devoted to Family Justice
Leo V. Diana’s path to the judiciary began with community service. He served as mayor (and earlier deputy mayor) of his hometown, Manchester, Connecticut, before his judicial appointment in 2014. Upon becoming a Superior Court judge, Diana quickly gravitated to family law – an area that deals with sensitive issues like custody, divorce, and child welfare.
Over the years, he took on increasing responsibility within the Judicial Branch. He served in the Middlesex (Middletown) and Norwich Judicial Districts, and from 2017 to 2021, he was the presiding judge of the specialized Regional Family Trial Docket in Middletown. This docket handles some of the most challenging family cases statewide, indicating the trust placed in him to handle high-conflict matters. By 2023, Judge Diana was the Presiding Judge for Family Court in Hartford and the Assistant Administrative Judge of that district.
Recognizing his successful track record, the Judicial Branch elevated Judge Diana to Chief Administrative Judge for Family Matters, effective September 4, 2023. In this top role, he collaborates closely with the Chief Court Administrator on policies and procedures that affect family courts statewide. His duties include implementing new programs, soliciting input from other judges and stakeholders, and ensuring consistency and efficiency across all family courts. It is a role that amplifies his influence on family justice throughout Connecticut. Judge Diana has expressed profound honor at this appointment, while humbly noting the big shoes he fills after his predecessor guided the court through the pandemic.
Respected for Fairness and Integrity
Within Connecticut’s legal community, Judge Diana is held in high esteem for his even-handed judgment and ethical leadership. He has shown a strong ability to manage the most sensitive cases—often those involving children under challenging circumstances—competently and compassionately.
Notably, Judge Diana’s reputation extends beyond just colleagues. Even those who critique the family court system have singled him out as a model jurist. David Weigel, founder of the Family Court Fraud Warrior Project – an advocacy group that investigates corruption in family courts – has inducted Judge Diana into the project’s Judicial Hall of Fame for exemplifying the integrity that family courts should strive for.
Weigel, who has spent years exposing problems in family courts, was struck by Judge Diana’s approach when observing his courtroom. He remarked:
“I have spoken with thousands of families railroaded by the family courts. It was not until I observed Judge Diana’s court as a court watcher that I understood how much a conscientious and caring judge can make all the difference. Judge Diana asked about the children by name and was well-informed about what was happening in their lives. If we had more judges like Judge Diana, we would not have to worry about corruption and fraud within the process. He puts the interest of the children first – the way the system was designed.” – David Weigel, Family Court Fraud Warrior Project.
This extraordinary praise from a court reform activist speaks volumes. In Weigel’s experience, many families feel “railroaded” by the courts, but Judge Diana stood out for his personal attention to families and insistence on doing right by the children.
The fact that a vocal critic of the system effectively inducted Judge Diana into a hall of fame of exemplary judges is a testament to Diana’s fairness and integrity. It shows that even watchdogs view him as an ally in ensuring justice, not part of the problem.
Leadership in Reforming Family Courts
Beyond individual cases, Judge Diana has also been a leader in improving the family court system for all families. Upon taking charge as Chief Administrative Judge, he helped roll out Connecticut’s new “Pathways” case management system for family cases. This innovative approach, launched statewide in 2021, fundamentally re-engineers how divorce and custody cases are handled.
Under Pathways, each case is assessed and assigned the appropriate level of court resources and scheduling, aiming to reduce unnecessary court appearances and focus attention where it’s needed most. Judge Diana was directly involved in meetings with the Rules Committee and stakeholders to refine the Practice Book rules that enabled Pathways.
In early 2024, he facilitated a consensus among attorneys, judges, and policymakers on updates to these rules, indicating that no objections remained to the reforms he championed. His hands-on role in this project shows a forward-thinking mindset: he is not only applying the law but also improving the system’s efficiency and fairness. Other jurisdictions are now looking to Connecticut’s Pathways model as a potential exemplar for family court reform.
Judge Diana also oversees the training and accountability of guardians ad litem (GALs) and attorneys for minor children – the very people who speak for children’s interests in court. He serves as Chairperson of the Connecticut Judicial Branch’s Standing Committee on Guardians Ad Litem and Attorneys for the Minor Child in Family Matters. Under his leadership, this committee approves the curriculum for GAL training, vets the roster of eligible GALs/AMCs annually, and has procedures in place to remove any who don’t meet standards.
By guiding those who act as the voice of the child in contentious cases, Judge Diana helps ensure that children’s interests are effectively and ethically represented. Advocates for children’s rights have lauded the committee’s work in professionalizing GAL services, and having a judge of Diana’s caliber at the helm gives the community confidence that the “watchdogs” for children are being properly watched themselves.
Within the family law bar, Judge Diana is known to be approachable and collaborative. He frequently engages with attorneys, mental health professionals, and parent advocacy groups to gather input on improving family court processes. For instance, he has appeared at forums such as the Connecticut Council for Non-Adversarial Divorce to discuss challenges and encourage less adversarial approaches in custody disputes. By soliciting feedback and promoting alternative dispute resolution and mediation, he works to reduce the adversarial nature of family cases – again, with the well-being of children in mind (since protracted, bitter litigation often harms kids the most).
A Hallmark of Excellence in Family Court
Judge Leo Diana’s record stands as a powerful example of how a family court judge can have a profoundly positive impact on lives. His combination of legal skill, compassionate demeanor, and ethical fortitude has earned him admiration from both insiders and outside observers of the justice system. When tough decisions are required, he does not shy away from them – but he grounds them in thorough fact-finding and a sincere concern for the children caught in the middle. Judge Diana is willing to make hard calls when necessary to protect children, yet he remains fair by providing avenues for parents to make amends and reunite. This balanced, child-first approach is precisely what family courts strive for, and it sets Judge Diana apart.
His leadership in the administration of Connecticut’s family courts further amplifies his impact. By guiding reforms like the Pathways system and overseeing the quality of child representatives, he is helping to shape a more responsive and trustworthy court system. He has been described as a “tremendous asset” to the judiciary by those in charge and as a hero by those who typically critique the courts. It is rare to find a judge who garners such universal respect, but Leo Diana appears to be one.
In an era when family courts often come under scrutiny, Judge Diana’s courtroom is a place where families can at least be assured that someone is truly listening and genuinely cares about the outcome for the children. His work exemplifies what it means to be a conscientious jurist. Through his rulings and reforms, he continuously reminds everyone of the core purpose of the family justice system: safeguarding children and strengthening families. By all accounts, Judge Leo Diana lives up to that mission every day, earning him a well-deserved reputation as one of Connecticut’s finest family court judges.
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