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Diddy’s trial began last week on May 5, 2025, and while his ex-girlfriend Cassie Ventura is testifying, attorney Anna Estevao is continuing the cross-examination.
Notably, Anna Estevao has been described as a “Top rated White Collar Crimes” attorney from New York City, as per Super Lawyers. According to her LinkedIn profile, Anna has been affiliated with Harris Trzaskoma LLP as a partner since May this year.
During the ongoing trial, Cassie Ventura, who is a well-known face in the entertainment industry, opened up about the 'freak-off' parties organized by Diddy in the past.
According to an indictment obtained by Page Six after Diddy’s arrest last year, the authorities reportedly found evidence related to the parties while they raided the rapper’s house in March 2024.
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In addition, Cassie also recalled certain incidents where Diddy had allegedly hit her. As per an update shared by ABC 13 Houston on May 15, 2025, Cassie told the court that she was in touch with Diddy through text messages, and one of them was shown to the jury as Anna Estevao said to Ventura:
“What about him made you fall in love with him?”
Cassie reportedly mentioned that she had not thought about the same for a while, and continued:
“The beginning of the relationship, I spoke about it already, it was really fast, fast-paced, scary. But the more time I spent with him and got to know him his real personality, or at least what I thought was his real personality, came out.”
However, Ventura dismissed the claims that she reportedly wanted to be a part of the freak-offs to keep Diddy happy, as per ABC 13 Houston. Estevao initially questioned Cassie about her relationship with Diddy, where Ventura agreed that her love for Diddy was one of the reasons she was hurt when the artist allegedly cheated on her.
Anna Estevao has been an expert in different matters: Career, education, and more
As mentioned, Anna is a resident of New York City. The official website of Harris Trzaskoma says that Estevao helps those clients who have not been charged and are under investigation by finding a way through which they do not need to pay anything.
Anna Estevao initially enrolled at Barnard College and obtained her JD at the New York University School of Law, as stated in her LinkedIn profile. She served as a law clerk to the Court of Appeals for the Second Circuit for a year.
Furthermore, Estevao was a trial attorney for the Federal Defenders of San Diego, Inc. She later shifted to Sher Tremonte LLP, where she was employed as a counsel. Anna served as a partner at the same company for five months this year before joining Harris Trzaskoma.
The legal firm’s website stated that Anna Estevao was chosen to be on the Southern District of New York’s Criminal Justice Act Panel. She helped an individual who was accused of cyberstalking and extortion, and since he was a non-citizen, Estevao negotiated to change the charges to a non-deportable offense.
In another case, Estevao was able to reduce the charge to an offense misdemeanor and a probationary sentence for a client sentenced for importing synthetic cannabinoids. She has even represented a litigation finance company, investment advisers, and a former law enforcement officer.
Anna Estevao is also representing Diddy as a part of his defense team and has been an expert in matters such as bank fraud, sexual assault, extortion, wire fraud, and more, as mentioned in Harris Trzaskoma’s website.
As mentioned, Diddy's trial is ongoing, and as per CBS News, the first two witnesses in the case were Julian Phillip and Israel Florez. According to USA Today, Diddy was arrested in September 2024 on charges of sex trafficking, racketeering, and transportation to engage in prostitution.
