When The Ethics Reporter first reported on Courtny Osterling — admitted to the bar in 2011, appointed Chief Counsel of the Ninth Judicial District Grievance Committee in Westchester County — the question we asked was simple: how does someone with so little experience end up running one of New York's most consequential attorney discipline offices?

Readers responded with a question of their own: is he an outlier, or a pattern?

The answer is now clear. He is a pattern.

Two Offices. Two Inexperienced Chiefs. One Department.

The Appellate Division, Second Department, oversees attorney discipline across a vast swath of New York — Brooklyn, Queens, Staten Island, Nassau, Suffolk, Westchester, Rockland, Orange, Putnam, and Dutchess Counties. It does this through three grievance committees, each led by a chief counsel appointed by the court. Two of those three chief counsels are among the least experienced in the state.

Courtny Osterling — Chief Counsel, Ninth Judicial District Grievance Committee (Westchester, Rockland, Orange, Putnam, Dutchess): admitted to the bar in 2011. According to OCA registration records, he was working at an administrative office of the Office of Court Administration in Brooklyn as recently as 2022 before his appointment. He has approximately 15 years of legal experience.

David William Chandler — Chief Counsel, Grievance Committee for the Second and Eleventh Judicial Districts (Brooklyn, Queens, Staten Island): admitted to the bar in 2014 (OCA registration #5226287). A SUNY Buffalo Law School graduate. His registration history shows he has been employed at the Second Department's Grievance Committee since at least 2020 — meaning he may have joined the office within a few years of passing the bar. He has approximately 12 years of legal experience. He is the least experienced grievance committee chief counsel in New York State.

Together, these two men are responsible for investigating and prosecuting attorney misconduct across the most densely populated region of New York outside Manhattan. They make charging decisions that can end legal careers. They exercise prosecutorial discretion over thousands of complaints. They lead offices that are, for most New Yorkers, the primary institutional mechanism for holding lawyers accountable.

The Rest of the State Looks Very Different

To understand how anomalous the Second Department's choices are, consider who leads every other equivalent office in New York:

• Jorge Dopico — Chief Counsel, Attorney Grievance Committee, First Department (Manhattan, Bronx): admitted 1980. Georgetown University Law Center. 45+ years at the bar. He has led the First Department's discipline apparatus for decades and is considered one of the most experienced attorney discipline professionals in the country.
• Monica Duffy — Chief Attorney, Attorney Grievance Committee, Third Department (Albany and 26 upstate counties): admitted 1988. Nearly 38 years of legal experience.
• Catherine A. Sheridan — Chief Counsel, Grievance Committee, Tenth Judicial District (Nassau and Suffolk Counties): admitted 1994. 32 years of experience. Notably, the Tenth District is also part of the Second Department — and its chief counsel has more than twice the experience of Osterling and nearly three times that of Chandler.
• Cydney A. Kelly — Chief Counsel, Attorney Grievance Committees, Fourth Department (Buffalo, Rochester, Syracuse, and 22 counties across Western and Central New York): admitted 1995. 31 years of experience.

The pattern is stark. Departments 1, 3, and 4 — and even the Second Department's own Tenth District — are led by attorneys with 30 to 45 years of experience. The Second Department's two downstate committees, covering the largest population base in the state, are led by attorneys with 12 and 15 years respectively.

Why Experience Matters in This Role

Attorney discipline is not a function where youth is an asset and experience is optional. The Chief Counsel of a grievance committee is, in practical terms, a specialized prosecutor with enormous discretion. They decide which complaints warrant investigation, which investigations warrant charges, and how aggressively to pursue attorneys who have harmed their clients.

Those decisions require nuanced legal judgment built over years. They require familiarity with the full range of professional conduct rules, with the kinds of misconduct that attorneys actually commit, and with the institutional dynamics of the legal profession in a given region. A 12-year attorney making charging decisions about attorneys who have been practicing for 30 years — who may have appeared before every judge in the county, who know every local custom and procedural expectation — is at a structural disadvantage that experience cannot be wished away.

This is not a theoretical concern. Sources familiar with the Ninth District's internal dynamics — speaking to The Ethics Reporter for our earlier Osterling reporting — described a climate of concern among veteran staff. Antonia Cipollone, a 20-year veteran of the Ninth District office who was reportedly passed over for the chief counsel position twice, was described by sources as telling defense lawyers that Osterling lacked the experience the role required. Cipollone has not commented publicly.

Whether analogous dynamics exist at the Second and Eleventh District is something The Ethics Reporter has not yet been able to confirm. We have received no comment from that office.

Who Makes These Appointments — and How?

Under 22 NYCRR § 691.4, the Appellate Division of the Second Department appoints the chief counsel to each of its grievance committees. The court does so "in consultation with the committees." There is no public application process. There is no published minimum experience requirement. There is no announcement when a new chief counsel is appointed, and no explanation of why one candidate was chosen over others.

The First Department, by contrast, has maintained a tradition of highly experienced leadership in its discipline office — a tradition that appears to reflect a deliberate institutional value. The Second Department has made different choices, at least for two of its three downstate committees, and has not explained those choices to the public.

The Appellate Division, Second Department, did not respond to a request for comment from The Ethics Reporter. We asked specifically about the criteria used to select chief counsels and whether the court had any comment on the experience disparity between its committee leaders and those in other departments. We received no reply.

The Tenth District Exception

One detail that makes the Second Department's pattern harder to dismiss as accidental: its own Tenth District, covering Nassau and Suffolk Counties, is led by Catherine Sheridan, a 32-year veteran. The Second Department appointed her. The same court that chose Sheridan also chose Osterling and Chandler.

This means the experience disparity is not a department-wide preference for younger leadership. It is something specific to the two downstate committees — the ones covering Brooklyn, Queens, Staten Island, and the five-county region north of New York City. The most urban, highest-volume, most complex jurisdiction in the department is served by its least experienced leadership.

That is not a coincidence. It is a choice. And it deserves an explanation.

What the OCA Records Show

Both Osterling and Chandler's career trajectories, as reconstructed from OCA registration records and prior reporting, suggest something else worth noting: both appear to have spent the formative years of their legal careers inside the OCA or grievance committee system itself, rather than in private practice, prosecution, or other adversarial legal work.

Osterling's registration history, reviewed for our earlier reporting, showed his employment at an OCA administrative office in Brooklyn as recently as 2022. Chandler's registration history shows continuous employment at the Second Department Grievance Committee since at least 2020 — which, given his 2014 admission date, suggests he may have joined the office no more than six years after passing the bar, and has spent a substantial portion of his career there.

There is nothing improper about building a career in an institutional setting. But it raises a legitimate question about the breadth of perspective that chief counsels bring to a job that requires understanding how lawyers across the full spectrum of practice — solo practitioners, large firm partners, prosecutors, public defenders — actually work and what kinds of misconduct actually occur. Someone who has spent their entire career inside the discipline apparatus may have deep procedural knowledge of how the committee functions, but a narrower window into the profession they are policing.

The Public's Interest

New Yorkers who file complaints with the Second Department's grievance committees are entitled to know that those complaints will be evaluated by people with the judgment, experience, and authority to act on them effectively. Lawyers who are the subject of complaints are entitled to know that the prosecutorial decisions made about them are the product of seasoned professional judgment.

The appointment of inexperienced chief counsels does not guarantee that those standards will not be met. It does raise legitimate questions about whether the Second Department's appointment process is optimized for public accountability or for something else — institutional convenience, internal promotion from within, or preferences that have never been made public.

New York's attorney discipline system depends, ultimately, on public trust. That trust is earned through transparency about how the system works and who runs it. The Second Department has provided neither a transparent appointment process nor an explanation of why its downstate committees are led by attorneys with a fraction of the experience found elsewhere in the state.

That explanation is overdue.

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