Pittsburgh man may leave Big Island before manslaughter trial

  • Benjamin Fleming

A 37-year-old Army active duty soldier charged with manslaughter in connection with the death of a fellow visitor from Pittsburgh has been granted permission to leave the state.

Benjamin Fleming, of Pittsburgh, appeared in Kona Circuit Court Wednesday on a defense motion to reduce bail and return to the mainland pending trial for the March 29 death of Abhishek Gupta, also of Pittsburgh.


Fleming, who has been free since posting $250,000 bail, requested through his attorney Christopher Eggert a reduction in bail to $100,000. Eggert argued his client could only afford a $100,000 bail because his mother posted half of the bail through a bail bonds company who gave her 45 days to come up with the rest of the money.

“Either he posted the bail or he didn’t,” said Judge Robert D.S. Kim.

Eggert said he was concerned that if the full bond is not posted, it could be pulled and Fleming would have to return.

“That is not a concern of the court,” said Kim.

Deputy Prosecuting Attorney Chase Murray argued the bond has been posted.

“That is the only thing relevant at this juncture,” he said adding $250,000 is an appropriate amount for the charge.

Kim denied the motion to reduce bail and entertained the motion for Fleming to leave the state.

The state had no objection to Fleming leaving the state before his trial.

Kim granted that motion with the conditions that Fleming sign a waiver of extradition, surrender his passport, appear in person for all of his hearings and not leave the country without the court’s permission. When the condition of not owning or possessing a firearm was read, there was discussion of Fleming using a firearm in the course of his Army training. Kim acquiesced, and ordered him not to possess a personal firearm.

“He needs to come back for his hearings. If he doesn’t show up, I will order a bench warrant with no bail,” said Kim.

Eggert indicated that it was unlikely he would be ready for trial by the Aug. 3 scheduled date and would likely file a motion to continue.

After the hearing, Murray said the state had no objection to Fleming leaving the state because he had training scheduled with the Army and had the implied assurance of Fleming’s commanding officer that he would return to Hawaii for all court dates.

According to the website Poets and Quants, Fleming went to Tepper School of Business in 2018 from the U.S. Army where he had served as a communications specialist. All told, he has spent nearly 19 years in the Army, including a stint as a platoon leader of 24 soldiers that he led through training and more than 300 operations in Afghanistan.

Fleming’s LinkedIn profile said he was working an internship with a spaceflight professional association based in St. Petersburg, Florida, since June. Carnegie Mellon profiled Fleming in November as a an example of how the school helps veteran students, but the article has been removed from the school’s website.

Fleming was arrested March 29 after Hawaii Police Department officers were called to a vacation rental at the Kona Mansions Condominiums for an unconscious man who was not breathing following an altercation with his roommates. Medics, who were already on the scene, determined that the victim, identified as 30-year-old Abhishek Gupta, also of Pittsburgh, was already deceased.

A second man arrested at the scene, a 31-year-old New Jersey man, was released without charges.

An autopsy performed found the cause of death to be strangulation and manner of death to be homicide.

During a two-day preliminary hearing held April 7, the New Jersey man testified the three college friends had arrived on the Big Island on March 28. Alexander Germany-Wald said Gupta had gotten “psychotically” drunk and he walked him back to their Kailua-Kona Airbnb after Gupta was asked to leave a bar. Fleming stayed behind.

Germany-Wald said he locked himself in a bedroom to seclude himself from Gupta, who was angry about having to go back to the condo.

At one point, the two of them got into a fistfight, with Gupta on top of Germany-Wald and punching him. Fleming returned to the condo and “came to my aid and restrained Mr. Gupta,” Germany-Wald said during the preliminary hearing.


With Gupta laying in the hallway floor, Germany-Wald said Fleming joined him in the kitchen where they drank a beer. He testified that he could hear Gupta “snoring” in the hallway. They checked on Gupta after several minutes because they no longer heard him snoring and realized he wasn’t breathing. Fleming called 911.

Manslaughter is a class A felony that carries a maximum sentence of 20 years imprisonment.

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