Who Is Anna Estevao?
Anna Estevao is a New York-based criminal defense attorney who has built a reputation for handling complicated, high-profile, and often sensitive legal matters. She currently practices as a partner at Harris Trzaskoma LLP, a boutique litigation firm known for taking on cases that attract national attention. Her work spans white-collar crime, federal criminal defense, and complex commercial disputes, making her one of the more versatile litigators currently practicing in New York.
While she had already earned a strong reputation among peers and legal directories for years, Anna Estevao became widely known to the general public after her role in the criminal trial of Sean “Diddy” Combs. Her calm, methodical courtroom style during that case introduced her name to people far outside the legal community, and it set the stage for her later involvement in another headline-making matter involving former Venezuelan president Nicolas Maduro.
Early Life and Education
Anna Estevao’s academic path reflects the kind of preparation that typically shapes a strong trial lawyer. She earned her Bachelor of Arts degree from Barnard College in 2010, a school known for producing driven, independent thinkers. From there, she moved on to New York University School of Law, where she graduated in 2015 with a Juris Doctor, earning the distinction of magna cum laude.
During her time at NYU Law, Anna Estevao was recognized as a Root-Tilden-Kern Scholar, a prestigious honor reserved for students committed to public interest law. She also served as a Notes Editor for the NYU Law Review and was elected into the Order of the Coif, an academic honor society for law students who rank among the top of their graduating class. This combination of scholarship and leadership experience gave her a strong foundation before she ever stepped into a courtroom.
Career Beginnings and Early Legal Experience
After law school, Anna Estevao did not rush straight into private practice. She first clerked for the United States Court of Appeals for the Second Circuit, a role that exposed her to appellate reasoning and case law at one of the most influential federal courts in the country. This clerkship gave her firsthand insight into how judges evaluate arguments, which later shaped how she structured her own trial strategies.
She also spent time as a federal defender in California, representing indigent clients in federal court. During this period, she focused heavily on immigration-related offenses, gaining direct courtroom experience defending people who often had the fewest resources and the highest stakes. This early public-service work is often cited as a formative part of her legal identity, since it required both technical skill and genuine advocacy under pressure.
Seven Years at Sher Tremonte LLP
Anna Estevao spent roughly seven years building her litigation career at Sher Tremonte LLP, a respected New York firm known for criminal defense and civil litigation work. During her time there, she was promoted to partner in January 2025, a milestone that reflected years of consistent casework and client trust. Her practice during this period covered a wide range of federal charges, including tax fraud, mail and wire fraud, money laundering, and other financially complex crimes.
Beyond financial crimes, she also represented clients facing serious allegations such as sexual assault and immigration violations. Colleagues and legal directories have noted her ability to secure favorable outcomes even in difficult circumstances, including cases where judges were persuaded to impose probation instead of prison time. This period at Sher Tremonte helped cement her standing as a trusted name in New York’s white-collar defense community.
Moving to Harris Trzaskoma LLP
In 2025, Anna Estevao transitioned to Harris Trzaskoma LLP, joining as a partner just months after her promotion at her previous firm. Harris Trzaskoma is known for taking on complex and high-visibility cases, and the move positioned her to work alongside other well-known defense attorneys on some of the most closely watched trials in the country.
At Harris Trzaskoma, her practice continues to focus on white-collar crime, federal criminal defense, and sensitive regulatory investigations. She has also taken on work involving restitution and forfeiture, an area where she has reportedly had success in reducing the financial penalties her clients face after a conviction. This shift to a firm built around headline cases coincided with the period that would soon make her one of the most searched attorney names in the country.
Cross-Examining Cassie Ventura in the Diddy Trial
Anna Estevao’s most publicly recognized moment came during the 2025 federal trial of Sean “Diddy” Combs, where he faced charges including racketeering conspiracy and sex trafficking. As part of Combs’ defense team, she conducted the cross-examination of Casandra “Cassie” Ventura, the prosecution’s central witness and Combs’ former girlfriend. Ventura had testified about being pressured into drug-fueled sexual encounters that she and prosecutors referred to as “freak-offs.”
During the cross-examination, Anna Estevao presented jurors with emails and text messages from earlier in the relationship, aiming to portray Ventura as a more willing participant than prosecutors described. Legal commentators and major outlets described her approach as strategic and precise, while still handling emotionally difficult testimony with care. The jury ultimately acquitted Combs of the most serious charges, including sex trafficking and racketeering, though he was convicted on lesser prostitution-related counts. Her performance during this trial earned recognition from legal publications, including a spot on a notable list highlighting standout legal work that week.
Joining Nicolas Maduro’s Defense Team
Following her visibility from the Combs trial, Anna Estevao took on another major case in 2026, joining the defense team representing former Venezuelan president Nicolas Maduro. Court filings in the Southern District of New York confirmed her formal appearance as counsel in the case, which involves drug trafficking charges following Maduro’s removal from Venezuela.
She joined the team shortly after her colleague Barry Pollack, previously known for representing WikiLeaks founder Julian Assange, also joined Harris Trzaskoma. The defense has signaled plans to challenge the legality of how Maduro was brought into U.S. custody, describing the circumstances as highly unusual. Anna Estevao’s involvement in this case shows her continued role in some of the most legally and politically significant matters currently unfolding in the United States court system.
Recognition, Awards, and Legal Reputation
Anna Estevao has been named a Rising Star by Super Lawyers every year since 2021, a distinction awarded to a small percentage of attorneys based on peer recognition and a rigorous selection process. She is also listed as a top-rated white-collar crimes attorney in New York, reflecting consistent recognition from within the legal profession itself rather than just media attention.
Her admission to practice law spans multiple states, including New York and California, and she has appeared before both the Second Circuit Court of Appeals and the Southern District of New York. This breadth of courtroom experience, combined with her academic background and public-service beginnings, has shaped a reputation built on substance rather than simply high-profile headlines.
Conclusion
Anna Estevao’s career reflects a steady progression from academic excellence to public defense work, and eventually to some of the most closely watched courtrooms in the country. Her path through Barnard College, NYU Law, a federal clerkship, and years of hands-on trial experience shows a lawyer who earned her reputation gradually before stepping into the national spotlight. Whether through her work on the Sean Combs trial or her current role on Nicolas Maduro’s defense team, she continues to be a name closely associated with high-stakes, high-visibility criminal defense in the United States.
Frequently Asked Questions
Who is Anna Estevao? Anna Estevao is a New York-based criminal defense attorney and partner at Harris Trzaskoma LLP, known for her work in white-collar crime and high-profile criminal cases.
What is Anna Estevao known for? She is best known for cross-examining Cassie Ventura during the Sean “Diddy” Combs federal trial and for later joining Nicolas Maduro’s legal defense team.
Where did Anna Estevao go to school? She earned her B.A. from Barnard College in 2010 and her J.D. from New York University School of Law in 2015, graduating magna cum laude.
Which law firm does Anna Estevao work for? She currently works at Harris Trzaskoma LLP, after previously spending several years as a partner at Sher Tremonte LLP.
Is Anna Estevao involved in the Nicolas Maduro case? Yes, court filings confirm she formally joined Maduro’s defense team in 2026 as part of his legal representation in the Southern District of New York.
