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Sentencing in killing over gambling debt closes long court saga

Family photo of Bobby Calabrese.

Family photo of Bobby Calabrese. Credit: Kathy Calabrese

A compulsive gambler who lured a Long Beach man to his arranged slaying in 2004 to dodge a $17,000 debt finally has admitted "being a killer," a prosecutor said before a judge sentenced him Monday to 23 years in prison.

Mark Orlando, 50, had been serving 25 years to life in prison for second-degree murder in the death of Bobby Calabrese when a federal appellate court threw out his original conviction.

The former Bay Shore man pleaded guilty to first-degree manslaughter two weeks ago while facing another Nassau County Court trial. In doing so, Orlando admitted for the first time that while trying to seriously harm Calabrese, he or another person he was "acting in concert" with caused the 24-year-old's death.

Orlando’s former co-defendant, Herve Jeannot, 29, of Deer Park, committed suicide in Nassau’s jail after a 2010 verdict convicting him of murder in Calabrese’s death.

Prosecutor Stefanie Palma said at Monday’s sentencing that Orlando always had tried to minimize his involvement and blame Jeannot for Calabrese’s death in the Island Park shooting on Dec. 3, 2004.

But now Orlando has "admitted being a killer," Palma added, saying Orlando had held Calabrese so Jeannot could shoot him.

The prosecutor also said the defendant’s conviction "proves what everyone has known for the last 16 years, that this defendant had Bobby Calabrese killed."

Calabrese had been 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 prosecutors. They said Orlando paid Jeannot $4,000 to carry out the killing.

The Calabrese family told Nassau Supervising Judge Teresa Corrigan before she sentenced Orlando on Monday that the heartbreak of losing a son and sibling remains raw years later.

The victim’s mother, Kathy Calabrese, 62, his father, retired Long Beach police officer Robert Calabrese, 65, and his sister Gina Calabrese, 42, remembered him as a smart and popular young man who cherished his family and never refused anyone in need.

They said he had been a state wrestling champion who planned to take a test to become a police officer that was held the day after he died.

"It takes a subhuman coward to find a sucker to carry out such a sickening act … You know you are guilty," the victim’s mother said while addressing Orlando. "If it wasn’t for you, Bobby would be with us."

Calabrese’s sister said that while her brother’s killing "shattered" their lives, "Bobby’s light" or spirit still lives among them.

Orlando’s attorney, Dennis Lemke, extended condolences to the Calabrese family in court Monday. He said previously that his client will spend about three more years behind bars.

A federal appellate court in 2019 ruled Orlando had been denied his constitutional right to confront an accuser during his 2005 trial after a detective testified that Jeannot said during questioning that Orlando paid Jeannot to commit the murder.

Had Orlando gone to trial again, it would have marked the sixth trial in the case. Jeannot’s first two trials ended in hung juries and a state appellate court overturned Jeannot’s conviction at a third trial, before a guilty verdict at his fourth trial.

"This has been a long road for all of you," Corrigan told the Calabreses on Monday, saying she hoped the sentence would give them "some closure and peace."

The judge also admonished the defendant, who appeared in court virtually from Nassau’s jail.

"You’re going to pay for your actions here on Earth and you will ultimately pay for your actions when you meet your maker," Corrigan said.

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