Up on Humboldt Avenue, in a Dorchester neighborhood where many of the streets start with the letter H, there are some marvelous mentors who work with some great kids at the Trotter School, pushing education as a transformative elixir that changes lives and opens doors.

But on some of the streets that surround the Trotter, there are different sorts of mentors, amoral, cynical men who push the gangster lifestyle as they push drugs, recruiting teenagers with promises as slick as any corporate headhunter’s.

The police and prosecutors say 33-year-old Robert “Ribs” Heckstall was one of those men, a streetwise consigliere for the street gang known as H-Block.


“We identify really dangerous people and try to take them off the streets,” Suffolk District Attorney Dan Conley was saying, “and he was one of them.”

Heckstall has a long rap sheet, and did time on a gun charge, but he also beat the rap many times, sometimes because witnesses got cold feet. And in some cases they got cold feet because Ribs Heckstall was threatening them.

Court documents show that an H-Block member told Boston Police homicide detective Joe MacDonald that Heckstall was involved in the 2010 killing of 14-year-old Jaewon Martin, an innocent kid who was shot to death on a Jamaica Plain basketball court when another H-Block member mistook him for a member of the rival Heath Street gang. The witness claimed that Heckstall followed after the shooter’s car in his role as a gang mentor.

In an affidavit, MacDonald described Heckstall as a senior member of H-Block who directed younger gang members “to distribute narcotics and commit violent offenses for the benefit of the gang organization.”

Heckstall avoided being charged with Martin’s murder, but he was convicted of witness intimidation and sentenced to 2½ years for sending threatening text messages to a witness to the murder. Two H-Block members were eventually sent to prison for killing Martin.


Heckstall did his time and was back on the street, back in the life. But his freedom was short lived, thanks to some dogged police work and a young prosecutor who used a novel legal approach to fight the intimidation of witnesses that has become rampant in Boston.

In January 2014, police responded to a home invasion in an apartment on Maple Street in Roxbury. A couple told police they had been robbed by four masked men who pistol-whipped the husband at the apartment’s doorway. The robbers ransacked the apartment, taking $2,800 in cash and the woman’s iPhone. Before leaving, one of the gunmen tried to justify his actions.

“This is business,” he said. “It isn’t personal.”

Two weeks later, the woman called Boston Police detective Juan Diaz, saying she had used her iCloud app to locate her stolen iPhone at a location on Elm Hill Avenue in Roxbury. Diaz and Detective Eddie Hernandez were able to track the phone to a specific address.

Robert "Ribs" Heckstall.
Robert "Ribs" Heckstall.

Sergeant Detective Tom O’Leary led a posse of detectives and officers to the apartment on Elm Hill Ave, where a woman opened the door but was less than forthcoming. Hernandez activated the alarm on the stolen iPhone and all of a sudden a phone in the apartment started buzzing.

“Whose phone is that?” Diaz asked.

“That’s my phone,” replied Ribs Heckstall, who was visiting the apartment.

After the cops handcuffed Heckstall, they learned he was still on probation for witness intimidation and was wearing a GPS device on his ankle. Detective Ryan Mason called Heckstall’s probation officer, Bob Donnelly, who pulled the tracking data that showed Heckstall was in the apartment on Maple Street at the time of the home invasion two weeks before.


Assistant District Attorney Stacey Pichardo had just been promoted to the gang unit, and the first case that landed in her lap was Heckstall’s.

“Stacey is one of our rising stars,” Conley said of the 30-year-old prosecutor.

The case against Heckstall looked strong, a grand jury indicted him and his trial was scheduled for this month. But as the trial approached, the male victim of the home invasion got a series of anonymous texts, via an app that made it impossible to trace the sender:

We know where you live.

Get out of Boston.

Think about your family.

The victims left town, too afraid to testify.

Suddenly, a slam dunk looked like a missed layup. But Pichardo, who like the terrified victims had grown up in the Dominican Republic, was undaunted. She hit the law library and pored over Heckstall’s statements, looking for more evidence.

Pichardo built an argument around a 2005 Supreme Judicial Court decision which had established the doctrine of “forfeiture by wrongdoing.” In that case, Suffolk County prosecutors successfully argued that a man named Jermaine Edwards could be tried for a shooting and paralyzing a Boston taxi driver even though the prosecution’s star witness refused to repeat at trial the testimony he had given against Edwards before a grand jury.


The SJC allowed prosecutors to use the unchallenged grand jury testimony because Jermaine Edwards had called the witness from jail, telling him to keep his mouth shut. The SJC established in Massachusetts the legal concept that the law will not allow a man to profit from his own wrongdoing.

Pichardo was able to show that the language used in the text messages sent to the victim of the home invasion closely resembled those Heckstall had sent the witness in Jaewon Martin’s murder. She produced a recorded conversation in which a cocky Heckstall told a relative who visited him in jail last Monday that he’d be home soon, because the victims would not testify at his trial.

“That’s what I’m banking on,” Heckstall said.

She noted that Heckstall said he wouldn’t consider a plea deal until after he saw the witnesses against him in a courtroom. He wanted one last chance to intimidate them.

Judge Jeffrey Locke was persuaded and on Wednesday granted Pichardo’s motion to introduce grand jury testimony at trial even though it would not be subject to cross-examination.

Ribs Heckstall may be venal, but he isn’t blind. He saw the writing on the wall. He pleaded guilty and Locke accepted Pichardo’s recommendation for a 7-to-8 year sentence.

Given all the talk about immigration these days, there is a certain irony to Heckstall, born and raised in Boston, being sent away by a prosecutor who came here from the Dominican Republic when she was 14.


But then, Stacey Pichardo had better mentors than Ribs Heckstall.

Kevin Cullen is a Globe columnist. He can be reached at cullen@globe.com. Follow him on Twitter @GlobeCullen.