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The curious case of Robert Macedonio

Attorney Robert Macedonio at Suffolk County Court in

Attorney Robert Macedonio at Suffolk County Court in Riverhead on Jan. 27, 2016. The case file of the asset seizure case that Suffolk District Attorney Thomas Spota brought against Macedonio, Clyde Ward and Larry Demetrius was sealed without explanation. It was photographed the same day in the office of the Suffolk County Clerk. Credit: James Carbone; Newsday / Will Van Sant

In December 2008, veteran criminal defense attorney Robert Macedonio appeared in a Suffolk County courtroom, this time as a defendant. “It’s embarrassing for me to be standing here,” Macedonio told Judge James Hudson as he pleaded guilty to felony cocaine possession.

The plea cost Macedonio his law license. A career that saw him rise from a junior Suffolk County prosecutor to a sought-after attorney for high-profile defendants appeared over.

But three years later — under unusual circumstances that have been largely hidden from public view — Hudson and District Attorney Thomas Spota allowed Macedonio to reduce his felony conviction to a misdemeanor, paving the way for him to regain his law license.

Macedonio got his second chance under a legal provision designed to correct miscarriages of justice, such as when new evidence clears the innocent or when prosecutorial error or fraud undermines a conviction. Such circumstances have not been publicly disclosed in the Macedonio case, raising questions of how an attorney with long-standing ties to Suffolk County’s law enforcement system faced no opposition as he successfully wiped away his felony guilty plea.

Answers to those questions are elusive because so much of the Macedonio case — from the investigation to the prosecution to the vacated felony conviction — remains secret. Records have been sealed without explanation or were not filed at all. One batch of documents at the county clerk’s office has been hidden from the public in a manila envelope bearing the following handwritten message: “This envelope as well as why sealed is sealed!”

Newsday obtained some of the sealed records, and they reveal that behind what appears on the surface to be a routine drug possession case was actually an extensive investigation by Spota’s office into financial crimes that included mortgage fraud.

The records show investigators spent at least a year probing alleged criminal activity involving Macedonio, and they uncovered enough evidence to convince judges to authorize them to raid Macedonio’s law office and seize his bank accounts and property.

An investigator would allege after the raid that Macedonio had used his law firm’s escrow account to launder funds in a mortgage fraud scam. Prosecutors would file court records estimating that the proceeds of the alleged criminal schemes tied to Macedonio exceeded $4 million.

Despite the allegations and the resources poured into the DA’s investigation, the results were minimal. The criminal charges against Macedonio and four associates linked to him were either dropped or ended with light plea deals, and none of the targets received more than nine months in jail. The available records do not explain how an ambitious financial crimes investigation into Macedonio ended in a simple drug possession charge.

Newsday asked Hudson to unseal records from the case, including the search warrant affidavit investigators filed with him to justify the raid of Macedonio’s office. The document could reveal the evidence investigators had gathered and, for the first time, allow the public to consider the merits of the district attorney’s pursuit of Macedonio.

Hudson has scheduled a Thursday court hearing on the matter to consider any objection the district attorney may have to unsealing.

The full account of what happened in the Macedonio case is contained in the records compiled by Spota’s office. In May, Newsday filed a Freedom of Information Law request for those records and was told that the case generated 17 boxes of material. Spota’s office initially said the records would be made available after each document had been reviewed. No records have been provided thus far.

Spota declined to be interviewed for this story. Christopher McPartland, the Suffolk prosecutor who handled the Macedonio case, also declined an interview request. McPartland, who is Spota’s top aide and foremost public corruption prosecutor, is reportedly the subject of a grand jury examination into whether he helped cover up former Suffolk police chief James Burke’s alleged beating of a suspect in custody.

Spota’s spokesman, in an emailed statement, criticized Newsday for pursuing “rumors” about the Macedonio case and vigorously defended the office’s handling of the matter.

“The suggestion that anyone in the District Attorney’s Office did anything improper in this case demonstrates a reckless disregard for the truth,” the email says. (The entire statement is available at

The statement says the Macedonio case was not unusual and claims that more than 150 people have received similar treatment during Spota’s tenure. The district attorney’s office refused to release details about those cases.

To be sure, defendants have had their felony convictions reduced to misdemeanors, but the way it happened in the Macedonio case appears to be unique.

Macedonio pleaded guilty to a felony, and before he had completed his conditional sentence, was placed on probation. Then, before finishing that period of probation, Hudson vacated Macedonio’s original felony conviction and replaced it with a misdemeanor.

A Newsday computer analysis of more than 400,000 felony cases prosecuted on Long Island over the last three decades found no other cases matching this pattern.

Joseph Conway, a former federal prosecutor and one of Long Island’s most prominent criminal defense attorneys, represented Macedonio and negotiated the arrangement that saw his client’s felony drop to a misdemeanor. Conway said he knew of no similar cases.

“Are there any others out there? It’s hard to believe there’s not another like it, but I’ve never been involved in a case like it,” said Conway, who maintained that his client’s ties to Suffolk County’s law enforcement community did not earn him special treatment.

Bennett Gershman, a Pace Law School professor and former prosecutor, called the handling of the case “bizarre” and “suspicious.” He said he is particularly disturbed that the law had been, in his opinion, improperly applied to benefit Macedonio.

“This is just totally irregular,” Gershman said. “It’s a special way of dealing with a particular case in a very unique, irregular, unprecedented way.”

Macedonio, during a brief phone conversation with a reporter, said there was “nothing underhanded” in his case and that he “welcomed the scrutiny.”

“It’s not a story to write anything negative about,” Macedonio said. “It’s the comeback kid.”

He ultimately declined to be interviewed.


Macedonio’s ties to local law enforcement and the legal community trace back to his great-uncle, Salvatore, who was one of the Suffolk Police Department’s original officers. Macedonio’s father, Carmine, was a detective who spent 23 years in that department, a decade of which coincided with Spota’s tenure as a prosecutor under former Suffolk DA Patrick Henry.

Macedonio graduated in 1985 from Riverhead’s Mercy High School, where he was the shaggy-haired co-captain of the football team. He studied criminal justice and business as an undergraduate at St. John’s University and earned his law degree from New York Law School in 1992.

His first job upon graduating was with the Suffolk district attorney’s office as a prosecutor under Spota’s predecessor, then-DA James Catterson. In 1995, Macedonio and fellow prosecutor Michael Brown left to start their own criminal defense firm, where Macedonio also ran a real estate practice.

Macedonio’s social media posts seem to embrace the caricature of the flashy New York criminal defense attorney. There are photos of him holding a bejeweled champagne bottle in front of a Lamborghini; thanking rapper 50 Cent for gracing his daughter’s Sweet 16 party; showing off new Gucci sneakers; sitting courtside at New York Knicks games; and passing out Thanksgiving turkeys from trucks.

Macedonio’s supporters at a 2012 hearing to regain his law license spoke of the attorney falling prey to the temptations that come with success. Macedonio testified that after his marriage collapsed in late 2001, his drinking and cocaine use became a problem that he recognized only after his law partnership with Brown dissolved in 2005. (Brown declined to be interviewed.)

Rumors circulated in the court system that Macedonio had gotten too chummy with some of his criminal defendants. Suffolk County Judge Stephen Braslow testified during Macedonio’s license hearing that he once advised Macedonio to be wary of socializing with “50 cents and 25 cents and whatever these guys are,” presumably a reference to 50 Cent and his oft-arrested protégé Tony Yayo. Macedonio represented Yayo when he was charged with slapping the teenage son of a rival, and Yayo ultimately pleaded to a violation.

“You can’t be hanging around with the clients, whatever they’re doing or not because they have nothing to lose,” Braslow said he told Macedonio. “You do. You’re a lawyer. You have a law license.”


Suffolk district attorney’s office detectives raided Macedonio’s Central Islip law office on Jan. 23, 2008. With the county in the midst of what Spota would call an “explosion of mortgage fraud,” court records show the investigators were targeting Macedonio’s real estate dealings with multiple criminal clients.

Brett Carlson, a financial crime investigator for Spota’s office, had received a search warrant from Hudson that also authorized state Banking Department officials to take part in the raid. The warrant allowed Carlson to seize more than three years of records and computer hardware for an investigation into alleged crimes that included falsifying business records, grand larceny and criminal possession of a forged instrument.

Carlson’s affidavit, which would explain the evidence he’d gathered to justify a search of Macedonio’s office, was sealed and remains so more than eight years later. Carlson, whose online profile shows he’s now on a financial crimes task force with the U.S. Department of Homeland Security, did not respond to messages seeking comment.

State law requires investigators to provide the court with an inventory of seized property after a search warrant is executed. A Suffolk courts spokesman said that no such inventory was filed after the raid of Macedonio’s office.

Available court records identify Macedonio and four associates as targets of Spota’s investigators.

Clyde Ward, a Bay Shore felon previously convicted of crimes including forgery and sale of a controlled substance, worked as a sales manager at Macedonio’s mortgage brokerage. Another real estate company incorporated using Ward’s home address was operating from Macedonio’s office, according to the search warrant, which authorized investigators to retrieve the company’s materials.

Suffolk prosecutors charged Ward with conspiracy and scheme to defraud, both felonies. He admitted to transporting and selling crack cocaine, and, while working for Macedonio, “providing false documents to lending institutions, issuing false certificates of income and false certificates of appraisals.” Ward, in a court hearing, stated that his criminal activity enriched Macedonio’s mortgage brokerage.

He pleaded guilty to misdemeanors and was sentenced to nine months’ imprisonment.

In a brief interview, Ward declined to elaborate on why the DA’s office linked his criminal case to Macedonio’s. “I don’t think Bob had anything to do with it,” Ward said. “I think he got caught up in it.”

Also charged following the investigation was Larry Demetrius of Islandia. Demetrius had been previously represented in 2003 by Macedonio’s law partner, Brown, when he was caught with three bags of crack cocaine and convicted of criminal possession of a controlled substance. He was arrested again on the same day investigators raided Macedonio’s law office, and prosecutors charged him with selling cocaine to drug dealers and grand larceny for defrauding a bank to obtain a mortgage. Demetrius pleaded guilty to felony attempted conspiracy and spent less than two months in jail. He could not be reached for comment.

Two days after the search warrant was issued, a judge’s seizure order authorized prosecutors to confiscate assets owned by Macedonio, Demetrius and Ward for alleged criminal activity that included “falsifying business records, offering a false instrument for filing, scheme to defraud and grand larceny.” The assets included “bank accounts, personal property and other real property in the amount of $4,159,980.00.”

James Cohen, an associate professor of law at Fordham University who reviewed available records in the case, said the figure indicates that investigators had pegged proceeds of the alleged criminal activity linked to Macedonio, Ward and Demetrius at just under $4.2 million.

Conway said Ward and Demetrius rented space in Macedonio’s law office and were the ones responsible for the mortgage fraud targeted by Spota’s investigators. Conway did not provide Newsday with evidence to support that claim, or any document concerning Macedonio’s case.

“It was bad judgment on his part to get involved with these guys,” Conway said of Macedonio. “At the end of the day, it was clear that he had no role in any mortgage fraud or financial fraud.”

Demetrius and Ward, however, had no apparent involvement in what the district attorney’s office referred to as a “related case” involving a real estate deal Macedonio facilitated for a convicted burglar flush with cash.

Vincent Rago — a felon the attorney had previously represented — and Rago’s wife obtained a home loan after Macedonio allegedly helped launder $200,000 in cash using his law office’s escrow account, according to investigators.

Carlson, in a May 2008 affidavit to support the seizure of the Ragos’ home, stated that he had been “involved in a long-term investigation regarding mortgage fraud being committed by multiple individuals,” including Macedonio.

“Macedonio is under investigation for this and other fraudulent activity,” Carlson attested. After he had “reviewed numerous bank records” for Macedonio’s escrow account, Carlson stated that he discovered it had been “used in connection with various other criminal activity.”

Conway said Macedonio “had no idea” that his escrow account had been used, as prosecutors alleged, to launder money in the Rago case.

Authorities ultimately dropped the prosecution of the Ragos. The couple’s criminal defense attorney, Robert C. Gottlieb, said he believed the case was abandoned due to a lack of evidence.


Although the available documents point to a financial crime investigation, Conway said the Macedonio case actually began as an investigation into the drug world. Investigators used wiretaps or other audio recordings, Conway said, and individuals targeted by investigators cooperated against Macedonio by providing information about the illegal drug activity in his law office.

“They would see him do the drugs or have people come in and give them drugs or him give drugs to other people,” Conway said.

Macedonio was ultimately arrested in December 2008 — nearly a year after the raid of his office — and charged with a single instance of felony drug possession. Charging documents state that Macedonio possessed at least a half gram of cocaine “on or about January 1, 2003 and December 1, 2008.”

Macedonio pleaded guilty to the drug possession charge on the same day he was arrested. A felony conviction in New York results in the automatic loss of an attorney’s law license, so the guilty plea effectively ended Macedonio’s law career.

Macedonio also settled the civil asset seizure case with Spota, paying $50,000 in return for the real estate and other assets seized by the district attorney’s office.

Conway said there were extensive negotiations over what criminal charges would be brought against Macedonio and that Spota said he would have charged Macedonio with financial crimes if he had sufficient evidence. “He said, ‘If we had him on the mortgage fraud, we would take him on the mortgage fraud,’” Conway said of Spota. “And I had no doubt.”

Asked if prosecutors threatened to charge Macedonio with cocaine distribution, Conway replied: “It was mentioned.” Conway said Macedonio only shared cocaine with friends and “there was never any allegation of trading coke for money.”

During court testimony, Macedonio said his cocaine possession occurred in 2004. Records do not explain why Macedonio pleaded guilty in 2008 to possessing cocaine four years earlier. Conway said that was the instance for which there was the strongest proof, though he could not recall what proof that was.

Hudson sentenced Macedonio to three years of conditional discharge, a sentence without the supervision requirements of probation, and directed him to avoid “injurious or vicious habits” and “disreputable persons.”

After his sentencing, Macedonio apologized to Hudson and Assistant District Attorney McPartland for causing what he called a “difficult” situation. He vowed a return from disgrace, telling the judge: “I will make you, as well as my family, proud once again.”


There’s a provision in New York state law — Article 440 — that was conceived to erase criminal convictions, including those later determined to be miscarriages of justice. The provision can nullify legal decisions that were “unauthorized, illegally imposed or otherwise invalid as a matter of law.”

The language of the law itself provides specific examples of the sort of injustices it can remedy: fraud on the part of the prosecutor, evidence known to be false when it was introduced, a defendant who was unfit to stand trial due to “mental disease or defect” or exoneration by DNA.

Suffolk County resident Marty Tankleff, in one of Long Island’s most well-known cases, filed an Article 440 motion to vacate his conviction for murdering his parents after new evidence surfaced. The provision helped Tankleff convince an appellate court in 2007 to order a new trial for him, after he had already spent 17 years in prison. Spota, who did not handle the initial prosecution but had fought to uphold the conviction, instead dropped the charges against Tankleff.

Macedonio used the same legal provision to overturn his felony conviction. In 2011, before Macedonio even completed the term of his initial three-year conditional discharge, Conway successfully argued that the felony judgment should be set aside through the application of Article 440.

Conway’s motion, which might explain why Macedonio’s circumstances met the standards set by the Article 440 provision, is not in the case file. Conway said he was surprised to hear that his motion was not available but did not provide the document to Newsday.

The motion, Conway said, argued that Macedonio had conquered his substance abuse problems and should be allowed to benefit from a drug diversion program established following his conviction. The case file does include a brief reply from McPartland stating that prosecutors did not object to Conway’s motion.

Gershman, the Pace Law School professor and former prosecutor, said he had never encountered another case where a defendant used an Article 440 motion to overturn a judgment on the grounds that he had reformed.

“It’s a misuse of the law, with the prosecutor’s and the court’s apparent consent, to reach a result that is absolutely not contemplated by this law,” Gershman said.

A transcript of a July 2011 court hearing shows Hudson gave no reason when he agreed to vacate Macedonio’s conditional discharge sentence, and there is no written justification from Hudson in the case file.

State law demands that a court “must set forth on the record its findings of fact, its conclusions of law and the reasons for its determination” when vacating a sentence. In an interview concerning his decisions in the case, Hudson said that he believed he’d met the requirements of the law because of prosecutors’ support.

“By stipulating to the motion, they were essentially saying those factors were present in the case,” Hudson said. “So there was no need for me to provide them.”

Fordham associate professor Cohen called Hudson’s explanation “nonsense,” and Pace Law professor Gershman said the judge had been “careless and negligent” by offering no justification for his decision.


Suffolk prosecutor McPartland, who had previously helped secure Macedonio’s conviction, backed Macedonio’s effort to vacate the felony judgment.

A court transcript shows McPartland sided with Conway’s argument that Macedonio should be allowed to enter a judicial diversion program that allows felony drug offenders “a second chance.” The program, which took effect in October 2009 — nearly a year after Macedonio pleaded guilty — allows nonviolent felony drug offenders to receive treatment rather than prison time.

The court, McPartland said, should impose a new judgment sought by Macedonio’s attorneys: one year of probation, during which Macedonio would be monitored for drug and alcohol use.

Hudson imposed the probation and praised prosecutors, saying McPartland “shows that he’s concerned not just with the letter of the law, but the spirit of justice as well.”

Conway and McPartland again appeared before Hudson in January 2012 so that Macedonio could plead to a misdemeanor drug charge. Hudson vacated Macedonio’s 2008 felony conviction, even though only five months had elapsed since the judge had placed him on a yearlong probation. Once again, Hudson failed to explain his decision and later said there was no need because prosecutors supported the move.

Macedonio credited Hudson and Spota’s office for allowing him to vacate the felony and instead plead to a misdemeanor.

“I would like to thank the court as well as the district attorney’s office for courtesies extended to me throughout this case,” he said.


Macedonio’s final obstacle to regaining his law license was convincing an appellate court at a June 2012 disciplinary hearing that he was worthy of a return to practicing law.

Macedonio’s wife, ex-wife and substance abuse counselor spoke on his behalf at the hearing in a Hauppauge courthouse, during which Macedonio discussed his past drug abuse and his 43 months of sobriety.

“I’m no longer in denial,” Macedonio said. “I’m here. I woke up.”

Macedonio, who testified under oath for the proceedings, did not discuss the details of the criminal case against him. Asked by his own attorney, David Besso, to describe “the basis of your arrest,” Macedonio responded only: “Possession of cocaine.”

Acting as a prosecutor for the proceeding was Michael Kearse of the New York State Grievance Committee, which oversees lawyer discipline. When Kearse asked whether the resentencing deal he received was common in Suffolk, Macedonio hedged.

“I’m not going to say common,” Macedonio said. “Every negotiation is different. Every criminal case is different.”

Kearse asked Macedonio whether there had been “any allegations during the investigation of you that you were involved in the sale of narcotics?”

“No,” Macedonio replied.

The financial aspects of the Macedonio investigation, which were likely unknown to the grievance committee because the documents had been sealed, were never raised during the hearing. When reached by a reporter, Kearse said he could not comment.

Fordham associate professor Cohen, who reviewed a transcript of the hearing, criticized Kearse’s failure to probe the more unusual aspects of the Macedonio case that were available. Cohen added that he was especially troubled that Suffolk authorities’ secretive handling of the case had effectively hidden the financial fraud investigation from bar authorities, who typically treat financial misconduct allegations more harshly than drug possession.

Noting that Macedonio “now stands convicted of a misdemeanor offense and remains drug free,” the panel of five appellate judges unanimously ruled to allow him to immediately resume practicing law.

Among those testifying in support of that decision were four sitting Suffolk Supreme Court justices: Stephen Braslow, William Condon, Ralph Gazzillo and Jeffrey Arlen Spinner.

The four justices each said in interviews that they were unaware Macedonio had been investigated for financial crimes, or that unusual judicial decisions had wiped away his felony conviction. And each of them said having that information would not have significantly affected their testimony.

“I was in favor of him being reinstated,” Braslow said. “As far as the legal situation that got him there and got him back, I have no idea what happened. I never asked.”

With Matt Clark

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