Drop Dead Serious With Ashleigh Banfield

Episode: “TOO EASY LOL”: 5 Fugitives Still Loose After New Orleans Jailbreak
Release Date: May 23, 2025

1. Introduction to the New Orleans Jailbreak

In this riveting episode of Drop Dead Serious, host Ashleigh Banfield delves into a shocking jailbreak that unfolded at the Orleans Parish Justice Center in New Orleans. Banfield sets the stage by describing the audacious escape of ten inmates, five of whom remain at large as of the recording date. She emphasizes the brazen nature of the breakout, highlighting its almost comedic audacity:

“Ten inmates escaped from the Orleans Parish justice center, and five of them are still on the loose as of this recording. They are somewhere out there.”
[00:00]

2. The Mechanics of the Escape

Ashleigh recounts the unconventional method the inmates employed to flee custody. At approximately 1:01 AM on May 17, ten inmates orchestrated their escape by unbolting a toilet and crawling through a hole in the back wall of their cell. Banfield paints a vivid picture of the escape route:

“They unbolted a toilet, they crawl out through the back wall... behind the toilet, there was a hole, a big, square hole in the wall.”
[00:00]

The inmates left taunting messages such as "Too Easy, LOL" and "the opjc, the Orleans Parish Justice Center" above the hole, signaling their success. They navigated through a maintenance passage to the jail’s loading dock, where they made their dramatic exit, including a notable incident where one inmate fell while seemingly carrying a blanket—later revealed to have been used to tamper with barbed wire, making their escape path less hazardous.

3. Profiles of the Escaped Fugitives

The episode provides detailed profiles of the escaped inmates, emphasizing the severity of their charges. Many of these individuals were accused of violent crimes, including murder, attempted murder, rape, and kidnapping. As of May 22, five remain free:

• Antoine Massey
• Leo Tate
• Jermaine Donald
• Van Buren
• Derrick Groves

Banfield underscores the danger these fugitives pose:

“These were violent offenders... charged with second-degree murder.”
[00:05]

4. Immediate Aftermath and Recapture Efforts

Of the ten escapees, five have been apprehended within a short timeframe and within close proximity to the jail—none ventured far, increasing their likelihood of re-incarceration:

• Kendall Miles was found hiding under a car in the French Quarter mere hours after the escape.
• Robert Moody and Gary Price were captured shortly thereafter.
• Corey Boyd and De Kenan Dennis were apprehended after six days on the run.

Banfield criticizes the inmates' apparent lack of strategy:

“Like, if that was me, I would not be hanging out within 10 miles at the jail.”
[00:04]

She highlights the ongoing threat posed by the remaining five fugitives, urging the public to remain vigilant.

5. Systemic Failures and Sheriff’s Response

The episode shifts focus to the systemic issues that facilitated the jailbreak. Sheriff Susan Hudson attributed the escape to “defective locks and doors” and a compromised surveillance system—one-third of the cameras were non-operational, including those in the escape pod.

“The jail had faulty locks and broken doors and also dead cameras.”
[00:08]

Furthermore, the facility was severely overcrowded, housing over 1,400 inmates in a space designed for 900, a situation exacerbated by consistent budget cuts from the city council. The governor of Louisiana has since called for a comprehensive investigation and the relocation of inmates.

6. Inside Involvement and Accomplices

A significant revelation in the episode is the likelihood that the jailbreak was facilitated by an insider. Sterling Williams, a maintenance worker at the jail, is accused of aiding the escape by disabling the water system to remove the toilet without raising immediate alarms.

“Sterling has a story. He says the inmates told him that they would shank him if he did not do as they asked.”
[00:10]

Additionally, three women—Courtney Harris, Corvante Baptiste, and Connie Weeden—were arrested for assisting the fugitives post-escape. Their involvement ranged from driving inmates around the city to providing food and financial assistance, indicating a network of support that enabled the escapees to evade immediate capture.

7. Expert Insights on Prison Breaks

To provide deeper context, Banfield brings in former federal inmate Larry Levine, who shares his expertise on prison systems and the dynamics that can lead to such breaches. Levine discusses the manipulation tactics inmates may use to coerce staff into facilitating escapes:

“Inmates will offer staff all kinds of things to get what they want.”
[09:13]

He references high-profile cases, such as Joyce Mitchell from the Escape at Dannemora saga, illustrating how inmates often exploit personal relationships within the facility to orchestrate their plans. Levine also speculates on the motivations and planning behind Sterling Williams' involvement, suggesting that the escape was meticulously planned rather than a spur-of-the-moment decision.

8. Conclusion and Public Safety Advisory

In her closing remarks, Ashleigh Banfield issues a stern warning to the New Orleans community:

“If you happen to be in the New Orleans area, lock your doors. And if you know something, don't play vigilante. Call the tip line. Let the pros handle it.”
[12:00]

Emphasizing the severity of the situation, Banfield urges listeners to stay cautious and report any sightings of the fugitives to authorities, reinforcing the message that these individuals are far more dangerous than typical criminals.

Final Thoughts

Ashleigh Banfield's detailed exploration of the New Orleans jailbreak sheds light on the complexities of prison security, the vulnerabilities within the system, and the ripple effects of such high-profile escapes. Through firsthand accounts, expert interviews, and a thorough breakdown of the incidents, listeners gain a comprehensive understanding of the challenges faced by law enforcement in containing dangerous criminals and the critical need for systemic reforms.

Note: Timestamps are approximate and correspond to the segments within the provided transcript.