Gangland News 6/10/21

[mafiastudent]

High Powered Federal Monitor And Two Scam Artists Teamed Up As Crime Fighters And Business Partners

Gang Land Exclusive!

A plucky pair of brothers from the tony Westchester town of Pelham, NY who stole $2.8 million from scores of small investors nearly two decades ago will be back in federal court in Brooklyn next week. The duo, Philip Orlando, 54, and Anthony Orlando, 53, will have to explain why they have never made good on $1.6 million in restitution that they promised to ante up more than seven years ago when they received a no-jail sentence for their crime.

The brothers have been nothing if not creative since their arrests in 2007 for orchestrating a classic pump and dump scheme. Court records show they worked as cooperating witnesses for the FBI, and that a decade ago they helped the feds run a successful sting operation that snared a trio of high-powered scammers.

The sting was run out of the Manhattan offices that the Orlandos shared with an unusual business partner: former assistant U.S. attorney Bart Schwartz whose law enforcement resume includes serving as a top prosecutor who oversaw the historic Mafia Commission case in the 1980s, and who is currently the monitor for the New York City Housing Authority.

Schwartz, court records show, became one of the Orlando brothers' biggest boosters. In a letter submitted to Brooklyn Federal Judge Frederic Block as the judge was considering a proper sentence for the two men, Schwartz offered high praise for "Phil and Tony" whom he met in 2010.

"I was impressed with the way they faced up to their wrongdoing and made no excuses and did not blame others for it," Schwartz wrote, noting that he was also "impressed with the ethical way they approached business and personal decisions" and found that "more and more I turned to them for business advice and valued their judgments."

At the 2014 sentencing, however, Judge Block questioned the brothers' failure to make good to the victims of their scam in the seven years since their arrest. Philip Orlando's lawyer, Michael Bowen, cited "financial uncertainty." He said the brothers were committed to paying $10,000 a month toward their restitution bill and would fork over a "balloon payment" of $250,000 in 2015, and each succeeding year.

Schwartz also urged the judge to have patience for his associates. "I understood that they had worked diligently to make good to the victims of their illicit activities and had demonstrated remorse and respect for law enforcement in other tangible ways," he wrote in his letter.

But there's little evidence that the brothers were worrying very hard about what they owed to people they had scammed as far back as 2002 and 2003. And it's not as though they can't afford it: Records show the brothers drive fancy cars and own several multimillion dollar homes. After the Orlandos won numerous postponements to pay up, federal officials finally ran out of patience. In 2019, the brothers were cited for a violation of supervised release (VOSR) for failing to make the required restitution.

The tangled tale took another turn in December when the Orlandos, and their company, Morningside Development, LLC, filed a lawsuit alleging that Schwartz, and several other well-off Westchester County residents who had also written sentencing letters on their behalf, had effectively cheated them out of $10 million they had earned from several entities and their subsidiaries.

The lawsuit demanded that Schwartz provide documents linking his firm, Guidepost Solutions, to the main defendant in the civil suit, Carriage House Partners LLC, (CHP) a Delaware company formed in 2009. CHP was formed by Anthony Lanza and the Orlando brothers after they had pleaded guilty and were cooperating with the feds. Among the new corporation's acquisitions, the lawsuit alleges, was Guidepost.

The records sought from Schwartz, the lawsuit alleged, would prove that CHP, and three of its executives, Lanza, Anthony Collura and Kevin Keane, had cheated them out of millions since 2014, the year they were sentenced.

Lawyers for CHP, Lanza and Collura strenuously denied the charges against their clients as well as the other defendants in the civil suit, calling them "baseless and demonstrably false allegations" in a letter to Gang Land.

Orlando attorney Steven Kessler, however, said his clients had helped the executives profitably expand their holdings. At the time CHP was formed, wrote Kessler, Lanza "owned 25 restaurants, but was looking for more satisfying business opportunities." The Orlandos, whom he had known since 2006, the lawyer wrote "provided the vision, expertise and contacts" in the business community.

When all the CHP paperwork was signed in 2010, Lanza owned 51% and Philip and Anthony Orlando each owned 15% of the company. In 2011, when CHP earned $3.9 million in bonuses in its partnership with Guidepost, "Anthony and Philip Orlando combined received $875,000 of those funds," according to the suit.

The Orlandos were "earning substantially more than $1 million per year" from their interests in CHP before 2015, Kessler wrote. But "Lanza, Keane and Collura began to tighten the knot on the Orlandos' finances" and since then, "They have not received a dime from any CHP-related source for any purpose, including consulting fees, distributions and bonuses," he wrote.

Lanza is CHP's managing member and Keane serves as the company's chief financial officer. Collura, who is CHP's general counsel, is also the chief legal officer for Guidepost Solutions.

Three months ago, on March 22, an attorney for Anthony Orlando told Judge Block that the civil suit was put on hold in February in the "hope" that former Magistrate Judge Steven Gold would be able to mediate the dispute, settle it by last month, and "determine the amount of money due the Orlandos, and by extension, the victims in this case."

No such luck, according to Kessler. Mediation is still continuing. But Schwartz and Guidepost Solutions made their peace with the Orlandos by agreeing to turn over the CHP-Guidepost related documents that the Orlando brothers were seeking, the lawyer told Gang Land. In return, Kessler said, Schwartz has been removed as a defendant from the civil lawsuit, which will be revived if the mediation effort fails.

Schwartz, and a second defendant "whom we sued only for documents that we could use against the remaining individuals and their companies" were dropped from the case, Kessler said. "Since they turned over the documents there was no reason for them to be kept in the litigation," he said.

Meanwhile, the Orlandos' undercover efforts for the FBI also ran into difficulty. Three men who were caught in the sting operation that the brothers helped run were charged with conspiring to steal "between $3 million and $4 million" in a stock scam between 2009 and 2011.

But the case against two of the defendants took a lousy turn two weeks before trial was slated to begin when prosecutor Patrick Sinclair, who had stated that Philip Orlando would be his key witness, announced that Orlando would not take the stand. Instead, he said he would play numerous Orlando tape recordings but that the FBI agent who had wired him up and monitored the recordings would testify, not Orlando.

Sources say Sinclair opted to use FBI agent Brendan Kenney to play the tapes because police arrested Philip Orlando for assault in June of 2012 in Riverhead, where, according to the real estate database Property Shark, the Orlando brothers still own two homes worth $2.7 million on Morningside Avenue, the genesis of the name of their company.

The Brooklyn U.S. Attorney's office declined to discuss the case. Former assistant U.S. attorney Sinclair, who prosecuted the Orlando brothers and who was set to use Philip as a key witness in a 2012 trial, told Gang Land that blaming their business partners for their failure to pay their restitution "was ridiculous."

"If you read the sentencing transcript," Sinclair said, "It's even more ridiculous because they haggled down from five years of restitution payments that I recommended would be a good schedule for repayment" to three years after talking to their lawyers. "They came back and said, 'No, we only want three years of supervised release, we think we can pay it in three years.'"

The record "seems to indicate" that when they were sentenced in 2014, "they had already decided they weren't going to make the payments," said Sinclair.

Sinclair declined to elaborate any further. But in their civil suit, Kessler wrote that before Lanza, Keane and Collura "began to tighten the knot" on the Orlandos, Philip and Anthony each earned $775,000 in 2012. In 2013 and 2014, Kessler wrote, Morningside Development received "compensation in the amount of $977,150 and $1,056,375, respectively."

Keane's attorney ignored calls and an email from Gang Land. But similar overtures to Steptoe & Johnson, attorneys for CHP, Lanza and Collura, were answered by a high-powered spokesman, Montieth Illingworth, who declined to answer a single question.

Instead, Gang Land received a letter from two barristers at a London law firm, Schillings Partners, headed "URGENT, NOT FOR PUBLICATION OR DISSEMINATION." The three page letter stated that the Orlando complaint contained "baseless and demonstrably false allegations" and "should not be published in full or in part" because the dispute has been settled.

"A confidential settlement agreement has been executed and is effective," the lawyers wrote, noting that the "lawsuit was voluntarily discontinued by the Orlandos and Morningside on February 5, 2021."

Orlando attorney Kessler noted that the suit was discontinued "without prejudice," which means that it can and will be renewed if no settlement is reached. "The dispute has not been settled," said Kessler. "I hope it is settled by Tuesday, but it is not settled."

Hopefully, any such settlement will include the seven figures the Orlando brothers still owe their victims.

Message From Turncoat Mobster John Pennisi: 'Talk To Me.'

John PennisiGreat news for folks looking to have a "one-on-one" conversation with John Pennisi, the turncoat Luchese mobster who has been talking up a storm about his decision to join Team USA back in October of 2018.

Pennisi is offering "unbridled, unprecedented access" that is "available to everybody" who has "an appetite" for hearing his stories of life on both sides of the law. Tom LaVecchia, the cohost of their MBA And The Button Man podcast, says it "is a great opportunity to learn more about John" and "to learn more about The Life."

Of course, it won't be free.

In a recent "quick and special announcement" of the podcast, LaVecchia stated that for an undisclosed "flat rate price" you can have a "one-on-one private Zoom chat (with Pennisi) in the comfort of your own home" in a new "sitdown series with John Pennisi" that the duo was "rolling out" to all comers after a "very successful" session with an unidentified customer.

As Gang Land reported last week, Pennisi revealed to podcaster Gary Jenkins that he was able to reach out to his deceased grandparents to ask their advice on whether he should turn himself into the FBI during some troubled times he was having three years ago with his former Mafia colleagues.

The first Pennisi sit down with a listener session took place recently and the Button Man half of the podcast declared that "it went good." The customer, Pennisi said, was seeking "advice about how to conduct himself in, like, a business meeting as compared to a sitdown. He was very happy he came away with some insight" and "asked me if I had wanted to become a life coach. I enjoyed it. I had a good time."

"This isn't some BS coaching program," LaVecchia insisted. "Once you kind of sit down and join the family, if you will, you'll keep in touch with John and keep in touch with me," said the MBA half of the podcast. "I'm no slouch in business," he continued. "I've done well for myself, so I wouldn't mind if anybody asks me anything."

In fact, the gentleman who had the initial "one-on-one with John, asked me some questions as well," LaVeccia said. "We spent a little over an hour. We had a great time."

John "will answer questions where he can, and you know he's pretty forthright," said LaVecchia. He noted that in addition to special insight about the mob, Pennisi "gives lessons about life and business" on the podcast, and "you can extract some value there" in a one-on-one talk, or even a "two-on-one" where you can share the cost of the session with a friend.

There is also a "broader webinar type thing where maybe you and a whole bunch of people" can have a group session with Pennisi that will cost individuals "much less money," said LaVecchia, sounding a little like the sideshow promoters Gang Land recalls seeing in Coney Island exhorting kids to c'mon in and meet the bearded lady and the two-headed chimpanzee.

LaVecchia didn't disclose the prices for any of the options, but he noted that "there is a fee structure" that is based on the "access that you want" as well as "your appetite and your budget." He instructed viewers to "click the link below" and fill out the form that asks for your name and email address. "Somebody will be in touch, and then we'll take it from there."

It's not likely that Pennisi will agree to chat with private investigators or defense lawyers for mobsters who have been convicted at trials where he testified, or that he'll let Luchese wiseguys who're expecting to be indicted based on information he's given the feds as customers of his "sitdown series with John Pennisi."

Then again, it wasn't likely when Pennisi was sentenced to a no jail prison term and given five years of supervised release last November that he'd be meeting up with ex-cons and cohosting a podcast that has aired more than 50 times. So you never know.

And since neither half of the podcast cited any parameters for the topics you could discuss with the Button Man or the MBA, it's likely that Pennisi would be willing to discuss, and maybe even expand on, the paranormal experience he had with his late grandparents that he shared with Jenkins.

As Gang Land reported last week, after praying to them and asking them to give him a sign to let him know if he should surrender to the FBI, Pennisi told Jenkins that he got an unmistakable one.

"I didn't live by a train station," Pennisi said. "You had to walk (there.) There was no planes flying around. It wasn't an earthquake. Gary, I swear to you, I had wine glasses and different glasses and dishes in the house. Everything was shaking in the house," he said in a high pitched voice, imitating the sound of glasses clicking, "bing bing bing bing bing bing."

"I even called my mother up and I says, 'I want you to listen to something.' This went on for hours. She says, 'What is that?' I says, 'It's the glasses. I prayed to Grandma and Grandpa. It's the glasses and the dishes and the house is shaking.' Gary, I can't even explain it. And THAT was my sign to go."

After Losing To The Jury, The Judge, And The Appeals Court, Boobsie Slams His Lawyer

What's a mobster to do? He made a dumb decision and rolled the dice instead of taking a sweet plea deal of eight-to-14 months in prison for gambling. At trial, he was convicted of gambling and racketeering and sentenced to 77 months. He then lost his appeal, as well as his motion for compassionate release from the judge who had hammered him on sentencing day.

If you're Luchese mobster Eugene (Boobsie) Castelle, you blame the lawyer who advised you to take the plea deal. You then file a motion asking the trial judge to grant you a new trial on the grounds that you were denied the effective assistance of counsel during your plea negotiation.

While Castelle has no one to blame but himself for being stuck in federal prison with a release date of September 10, 2025 instead of at home in Staten Island, his new appeal is doing better than he really has any right to expect.

Manhattan Judge Alvin Hellerstein ruled this week that his pro se motion "should not be summarily dismissed as being without merit." He ordered prosecutors to respond to Boobsie's filing within 60 days. He also directed Castelle's trial attorney Gerald McMahon to respond to his former client's assertions within 30 days, "under oath."

Castelle's version is this: He claims that he rejected the plea deal after McMahon advised him that if he were convicted of illegal gambling and racketeering, but acquitted of extortion, as he was, "he faced a guidelines sentence of 33 to 41 months imprisonment," not the 51-to-63 months guidelines that Hellerstein came up with on sentencing day.

Had McMahon "accurately advised movant," Castelle argued in his 17-page filing, "he would have accepted the government's 8 to 14 month plea offer."

Boobsie didn't mention that he was also not happy about the judge's decision to sentence him to 14 months more than his own recommended maximum prison term.

Contacted by Gang Land, the usually outspoken McMahon did not disappoint. He ripped the judge for his "senseless" guidelines finding, as well as his rulings at the trial, and Castelle for being less of a man than he always thought he was during the years he has known and represented him.

The difference between McMahon's 33-to-41 estimate and the judge's ruling of 51-63 months, McMahon said, was Hellerstein's "totally absurd" decision to "credit Castelle with extorting a gambling co-defendant that he was never even accused of extorting at any time," and adding points to his guidelines calculations.

"Pretending to be a great jurist who protects defendants' rights, Hellerstein says I should submit an affidavit under oath," said McMahon, who has already filed a one-page declaration stating that he advised Castelle that he "was facing approximately 33 to 41 months' if convicted of the gambling and racketeering but "acquitted of extortion."

"If he is so solicitous of a defendant's rights," McMahon said, "the judge should have allowed me to cross examine (turncoat mobster John) Pennisi about beating his girlfriend nearly to death for fooling around with Castelle. Instead," the lawyer continued, "he restricted my questioning of Pennisi and my closing arguments to the jury about the lowlife gangster."

"Too bad he didn't think about that during the trial," McMahon said.

"All I have to say about Mr. Castelle is that I am disappointed," said the lawyer. "I thought he was more of a man than that."

[mafiastudent]

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[elasticman]

I would love to cancel my subscription to Gangland News, it's quite useless at this point. But as soon as I do the DeSantis indictment will come down and I'll feel dumb for cancelling when I did.

[B.]

Thanks for posting.

He's obsessed with Pennisi to the point of parody. Capeci is talking more about the podcast than the podcast is talking about him. Not sure what Capeci's end game is with the open cynicism toward Pennisi and LaVecchia every week. Anything that keeps people interested in the mob in 2021 is a net positive for everyone who covers it.

Former mafia members write books and make movies, relatives of murderers get reality TV shows, etc. Franzese did his speaking tours and has his own little group of subscribers who pay him, now Pennisi is doing these webcam sessions for money. I don't see how any of it is ethically different. People find all kinds of ways to make money off the fact that they were in the mob and in today's world a big way to make money is through audience interaction online. I'm surprised it took this long for "Skype with a mobster" to hit the market.

Maybe Capeci should offer Skype sessions. I'd probably have more questions for him than I would some of the guys on the podcast circuit.

[Shellackhead]

Thanks for posting, anyone know when does DeSantis & co indictment coming?

[jimmy_beans8]

Who the brothers with? Or is it just nothin out there to report?

[Dapper_Don]

Wow...seriously IMHO this is a new low...or should I say Jerry keeps on stooping to a new low every week thus far in his obvious vendetta against Pennisi. Reporting a story about the Pennisi sitdowns as if it were a new thing, this started a long time ago the prices for the sitdowns are posted pretty publicly if he cared (or even knew) how to make his way around Youtube, etc. Capeci obviously has his stories all queued up and holds things back and saves them for other weeks, either that or this guy is really late to the ballgame sort of speak in terms of reporting on this. Defense attorneys, etc are obviously needling him to report things/giving him ideas on Pennisi as a drip drip pieces, to get under Pennisi's skin (notice Pennisi has made his IG private) and who knows get him violated or some law enforcement folks to start asking questions whether it is warranted or not.

[Dapper_Don]

I would love to cancel my subscription to Gangland News, it's quite useless at this point. But as soon as I do the DeSantis indictment will come down and I'll feel dumb for cancelling when I did.

I dont blame you for thinking of cancelling. You can always read it when its posted on BH from one other esteemed members of the forum.

[JohnnyS]

Thanks for posting ms.

Pathetic column this week though. Come on Jerry you're embarrassing yourself here.

[mafiastudent]

Another way to look at this is that Pennisi did complain in that blog post he wrote that Capeci didn’t plug their podcast like he supposedly said he would.

So, now he’s plugging it to make up for lost time.

[Tonyd621]

Another way to look at this is that Pennisi did complain in that blog post he wrote that Capeci didn’t plug their podcast like he supposedly said he would.

So, now he’s plugging it to make up for lost time.

Pennisi beat up that girl almost to death? that's news to me. anybody hear about that. or am I the last?

[SolarSolano]

Another way to look at this is that Pennisi did complain in that blog post he wrote that Capeci didn’t plug their podcast like he supposedly said he would.

So, now he’s plugging it to make up for lost time.

Pennisi beat up that girl almost to death? that's news to me. anybody hear about that. or am I the last?

What is the background on that? I like Pennisi but agree his shtick is getting old - but if he's hitting women than this LaVecchia guy is a fucking moron of a businessman for thinking this would work.

[newera_212]

Wow...seriously IMHO this is a new low...or should I say Jerry keeps on stooping to a new low every week thus far in his obvious vendetta against Pennisi. Reporting a story about the Pennisi sitdowns as if it were a new thing, this started a long time ago the prices for the sitdowns are posted pretty publicly if he cared (or even knew) how to make his way around Youtube, etc. Capeci obviously has his stories all queued up and holds things back and saves them for other weeks, either that or this guy is really late to the ballgame sort of speak in terms of reporting on this. Defense attorneys, etc are obviously needling him to report things/giving him ideas on Pennisi as a drip drip pieces, to get under Pennisi's skin (notice Pennisi has made his IG private) and who knows get him violated or some law enforcement folks to start asking questions whether it is warranted or not.

This is a really good point. Not that his column really needs to be a live, up-to-the-minute type of thing, because of the niche it serves... but still... I never really thought about that until you mentioned it: it really feels like he just has stories queued up on deck for weeks -> a month at a time, and if something big happens to go on between all of that, he can easily bounce a story off and replace it with something more breaking. Whatever, I'd probably do the same thing, can't fault him.

I'm happy GL still exists at the end of the day. But I think he's doing everybody a disservice when he simply recaps what was talked about or what happened on podcasts 2-3 weeks ago. A majority of his readers, besides a handful of Boomers or old timers, are probably listeners of those same very podcasts.

[Tonyd621]

that's the thing with Pennisi-his holier than thou routine. like he says on the podcast he can't work with convicted felons for and I quote "personal reasons"(if it's legal say it) and so many questions he won't answer...it's just about himself trying to look good. he deserves the capeci scrutiny because he offers zero transparency about himself.

[Rocco]

Jerry sounds a little jealous of Tom LaVecchia lol