Guilty plea ends long legal saga in case of Long Beach man killed over gambling debt

An ex-Bay Shore man who served prison time for murder in a 2004 slaying linked to the collection of a gambling debt pleaded guilty to manslaughter Tuesday after a federal appellate court threw out his original conviction.

Family members of victim Bobby Calabrese were in Nassau County Court as Mark Orlando, 50, admitted during a virtual appearance from jail that he took part in the 24-year-old Long Beach man’s killing. It happened on a small side street in Island Park on Dec. 3, 2004.

A Nassau jury had convicted Orlando of second-degree murder in 2005 and he was serving 25 years to life in prison before a successful federal appeal. In 2019, a federal court ruled Orlando had been denied his constitutional right to confront an accuser in court during his trial.

Had Orlando’s case gone to trial again, it would have marked a half-dozen trials in the case involving Orlando and his co-defendant, Herve Jeannot. Two of Jeannot’s trials ended in hung juries before his conviction at a third trial was overturned by a state appellate court. Then a guilty verdict at a fourth trial in 2010 preceded the 29-year-old Deer Park man’s suicide hours later at Nassau’s jail.

"It’s been a long battle," the slaying victim’s younger brother Chris Calabrese, 37, said Tuesday, expressing relief after Orlando’s guilty plea.

He thanked several members of the Nassau district attorney’s office for persevering in efforts to get justice for his sibling after five trials in the case.

"We were prepping for a sixth one. But given the circumstances, this was the best-case scenario," Calabrese added.

Nassau Supervising Judge Teresa Corrigan said she planned to sentence Orlando to 23 years in prison at a hearing scheduled for next month, a penalty the prosecution recommended under terms of the plea deal. Orlando agreed while pleading guilty to first-degree manslaughter that while intending to cause serious physical injury to Calabrese, he or another person he was acting in concert with caused the man’s death.

Orlando’s defense attorney, Dennis Lemke, said after court his client would serve about three more years behind bars under the deal.

"After 17 years it’s been a very long road, I’m sure, for the Calabreses as well as for Mr. Orlando and his family. To look at a situation now where he has about three more years before he’s released to be home with his family again is … an offer that he couldn’t turn down," the Mineola lawyer added.

Prosecutors have said Orlando paid Jeannot $4,000 to carry out the killing. Jeannot shot Calabrese in the head after jumping out from behind Orlando’s car and opening fire after the three men met up.

Calabrese was working as a bet runner, collecting money from gamblers, and had arranged to meet Orlando and Jeannot to collect $17,000 Orlando owed Calabrese’s boss, according to authorities. At first Orlando and Jeannot told police after the killing that they paid Calabrese the debt and he was alive the last time they saw him.

Jeannot later signed a written confession to the crime, but his lawyer said subsequently that Jeannot was an innocent bystander when Orlando pulled out a gun and shot Calabrese.

In ruling in Orlando’s favor on appeal, a federal court found a detective’s testimony at Orlando’s trial violated the confrontation clause of the Sixth Amendment. The detective testified Jeannot said during questioning by police that Orlando paid Jeannot to commit the murder.

The victim’s family previously described Calabrese as a warm and loving son and brother who had gotten mixed up in the illegal betting business for a total of six weeks and had been about to take an exam to become a police officer.

Brendan Brosh, a spokesman for Nassau District Attorney Madeline Singas, said in a statement Tuesday that his office continues to extend condolences to the Calabrese family.