Crime & Justice with Donna Rotunno

Episode: Harvey Weinstein’s Rikers Gamble & John Gotti’s Grandson’s Mercy Plea
Date: March 12, 2026
Host: Donna Rotunno | Guest: James Leonard, Criminal Defense Attorney

Episode Overview

This episode takes listeners into three high-profile criminal justice stories:

• Harvey Weinstein’s controversial interview from Rikers Island and its legal ramifications
• John Gotti’s grandson, Carmine Agnello's, plea for a lesser sentence to donate a kidney to his mother
• A dramatic attempted murder trial stemming from the Boca Bash involving a "90 Day Fiance" alum

Donna Rotunno and fellow defense attorney James Leonard dissect these cases, bringing in their personal experiences representing notorious clients and offering insider analysis on current legal strategies, media spectacle, and the human complexities behind the headlines.

[00:28] Introduction & James Leonard’s Background

• Donna introduces James Leonard, highlighting their mutual experience with high-profile cases.
• James details his unconventional path into criminal defense, coming from a law-enforcement family:

  "I guess the, the black sheep of the family. But...I was drawn to...big city criminal defense attorneys standing up for people defending their rights." – James Leonard [01:22]

• Cases handled:
  • Teresa Giudice (Real Housewives of New Jersey)
  • Members of Jersey Shore
  • Lil Kim, rapper
  • High-profile Atlantic City serial murders (subject of multiple documentaries and shows)
• Discusses the surreal experience of being recognized from TV in courtroom and jail settings.

[04:21] The Harvey Weinstein Rikers Island Interview

Background

• Donna: Full disclosure—she was Weinstein’s lead counsel in his landmark 2020 NY trial.
• Weinstein’s recent sit-down with The Hollywood Reporter is examined for its risks and implications.

Key Points

• Donna’s take: Interview unlikely to benefit Weinstein, given ongoing legal issues and relentless media framing.

  "For six years I've been telling Harvey probably best to not answer those questions, especially given the fact that he has cases still pending." – Donna Rotunno [05:29]

• James’s assessment:

  "Absolutely not. I think the interview was a disaster. I think it's ill-advised...None of it serves Harvey Weinstein." [06:24] "When you see it as a criminal defense attorney, you're cringing as you're reading it..." [06:58]

• Factors influencing Weinstein’s decision:
  • Possibly believed a former acquaintance-interviewer would be sympathetic (ultimately not the case).
  • Media dynamic: “The only entity that benefits...is the Hollywood Reporter and the reader.”
• Defense attorney dilemma:

  "A lot of times what happens is you get people...media strategists...Their voice carries weight...clients listen to people because...they are high profile for a reason and they have egos..." [06:44]

• Donna’s nuanced reaction:

  "Initially, the first thing I thought was a feeling of pity. I feel sorry for Harvey. I feel like Harvey has done his time. And I have said from the beginning...I thought Harvey Weinstein was guilty of sins and not crimes. And there's a big difference." [11:38] "I think he was made an example out of." [12:06]

• Both agree:
  • The interview didn’t change public perception.
  • In high-profile cases, “the emotion of the case” forever defines the person (James: [15:09])
• Discussion of possible redemption and Weinstein’s prospects for “controlling the narrative”—deemed slim in the current climate.

Memorable Quotes

• "The interview was a disaster...When you're a criminal defendant and you are in ongoing criminal proceedings, you should be listening to your criminal lawyer." – James Leonard [06:24]
• "I think Harvey Weinstein was guilty of sins and not crimes. And there's a big difference." – Donna Rotunno [11:38]

[15:52] Diddy at Fort Dix and the Role of Prison Consultants

Key Points

• P. Diddy now at Fort Dix, same prison Joe Giudice previously served time in.

  • Details of the facility:

    "When you go to the facility, you're going to a Air Force base...The federal prison part is a very small portion of this massive complex." – James Leonard [16:45]

  • Fort Dix considered low-security and preferable to other jails.
  • Diddy reportedly entered the RDAP (Residential Drug Abuse Program) for potential sentence reduction.

• Discussion of prison consultants:

  • Importance for high-profile inmates for navigation and mental preparation.
  • Some are helpful; others seek a payday.
  • "Experienced criminal defense attorneys...can do the same. But sometimes people that have worked within the system know better..." – James Leonard [18:50]

• Donna draws parallel to Mike Tyson’s comeback arc, questioning if Diddy could achieve similar public redemption after recent video evidence:

  "Mike Tyson turned his life around. The question is, does Diddy have it in him to do the same?...even though that's not what he was convicted of, that is what you will be convicted of in the court of public opinion." – Donna Rotunno [22:24]

[23:16] Boca Bash Attempted Murder Case

Background

• Annual ‘Boca Bash’ boat party in Boca Raton, Florida.
• Accused: Cole Goldberg; Victim: 90 Day Fiance alum (ex-girlfriend)
• Incident: After a day of fighting and drinking, woman jumped into water; claims Goldberg attempted to drown her ("strangle and hold her underwater"). Goldberg’s defense: He was "sinking, not strangling," and grabbed her to save himself.

Key Points

• The case is a bench trial (judge only):
  • James: Bench trials usually chosen after some assurance from the judge regarding potential outcome.

    "Every time I've done that, I've been successful. But I've never rolled the dice...without...a clear understanding of what I think the judge might do." [25:23]

• Donna:
  • Bench trials in Chicago often time-saving; sometimes called the "jury tax."
  • Speculates prosecution may be pressing despite victim’s own leniency.

    "Her testimony seems pretty clear that she was terrified...But at the same time, she's also saying, he's not a violent guy...I'm wondering if this is a prosecutor that just won't let it go." [27:04]

• James on the incident’s facts:
  • Assault allegedly continued in water: more dangerous than on boat.
  • Context: Alcohol involved, possible ambiguity about Goldberg’s intentions.
  • Plea deal offered: 6 months in jail, probation, apology letter—suggests prosecution recognizes complexity.

    "Any time you have a victim in court potentially advocating for a defendant, you don't want to be the prosecutor in that case." [29:52]

• Donna: Defense rejected the plea to avoid felony on record; outcome remains uncertain.

[31:36] John Gotti’s Grandson Carmine Agnello’s Sentencing and Organ Donation Request

Background

• Carmine Agnello, 40, grandson of John Gotti, requests reduced sentence to donate a kidney to his mother (Victoria Gotti).

Key Points

• James has personal knowledge of the family:

  "I do know the mother, Victoria. I've had dinner with her...They're great people, phenomenal people, all of them." [32:10]

• Is organ donation enough for leniency?

  "The question is, should that translate into a reduction of a sentence or any sort of consideration from the court? As a criminal defense attorney, I...think that it should. I don't know that it will." [32:40]

• Suggests using Agnello’s lack of criminal history and character as main mitigation argument.

• Acknowledges public/media pressure due to Gotti name may limit the judge’s ability to grant mercy.

• Donna agrees the action displays character and that sentencing should be about “painting the full picture.”

  "You can't find a more quintessential Italian family story than the, you know, gangster's grandson wanting to give up a kidney for his...family." [36:18]

• Both attorneys hope, but do not expect, mercy:

  "I hope that he gets the benefit of a fair and impartial sentencing that doesn't have anything to do with the reputation or legacy of the grandfather." – James Leonard [36:51]

Notable Quotes & Moments

• On representing notorious clients:

  "I go into courts and they'll say, 'I've seen you on television.' And I'm like, 'yeah, but now I'm here with you in the county jail.'" – James Leonard [03:28]

• On the futility of redemption narrative in Weinstein’s case:

  "Your view of Harvey Weinstein was what it was. And I don't think that interview changed it.” – Donna Rotunno [14:49]

• On the challenge of name recognition in sentencing:

  "He should definitely be judged for who he is and not for the legacy of his family." – Donna Rotunno [37:44]

Important Timestamps

• [00:28] – Start of episode, guest intro
• [02:16] – James Leonard’s past cases & notoriety
• [04:21] – Start of Weinstein case analysis
• [06:24] – James Leonard’s advice: never agree to Weinstein’s interview
• [11:38] – Donna’s emotional reaction to Weinstein story
• [15:52] – Diddy/Fort Dix/prison consultants segment
• [23:16] – Overview of Boca Bash attempted murder case
• [25:23] – Strategic use of bench trials
• [31:36] – Gotti grandson’s organ donation/mercy plea

Episode Tone & Style

• Conversational yet incisive; both attorneys share frank professional opinions with empathy for defendants as individuals.
• Humanizes high-profile trials, exposing legal strategies, media dynamics, and the personal costs behind public criminal cases.
• Frequent use of legal concepts explained in plain terms for general listeners.
• Candid, sometimes wry humor (re: “jury tax,” “quintessential Italian family story”).

Summary

This episode exemplifies how headline-grabbing crime stories are navigated not only in the courtroom, but in the court of public opinion, media, and personal legacy. Rotunno and Leonard offer rare behind-the-scenes insights, illuminating the legal, ethical, and human stakes for Harvey Weinstein, Carmine Agnello, and the array of lesser-known defendants caught in the crosshairs of America’s justice system.