He Pursued a Pardon in Trump’s Justice System. It Added to His Problems.

Not long after Michael Castillero was convicted in a Manhattan trial last fall in a $386 million fraud scheme, his pardon lawyer began drafting a letter to President Trump.

Mr. Castillero was a good man, a loving father and husband and an ardent backer of Mr. Trump, the lawyer wrote, but there was another reason the president ought to consider pardoning him: He was a target of “the Biden lawfare machine.”

“This is another case where a successful entrepreneur who is true MAGA is paying a price for his dedication,” the lawyer, Peter Ticktin, a longtime friend of the president, wrote in seeking a pardon for Mr. Castillero.

Not just that, Mr. Ticktin wrote. He noted that Mr. Castillero’s case in federal court for the Southern District of New York was initially overseen by Judge Jesse M. Furman, who “received scrutiny for his role in blocking the deportation of Mahmoud Khalil,” whom Mr. Ticktin described as “an antisemitic supporter of the Hamas terrorist group attending Columbia University.”

And, Mr. Ticktin added, a separate civil suit against Mr. Castillero, brought by the Securities and Exchange Commission, went before another Southern District judge, Lewis A. Kaplan, who “has drawn criticism for his handling of the civil trial brought by E. Jean Carroll against you, Mr. President.”

In years past, such naked appeals to a president’s sense of grievance might have been unusual, to say the least. But under President Trump, using all available arguments to seek a pardon has become almost standard practice, as much a part of diligent lawyering as filing briefs or making objections at trial.

“There’s no world these days in which I don’t at least discuss it with clients,” said Lawrence Lustberg, a prominent New Jersey lawyer who did not represent Mr. Castillero but had a client whom President Trump pardoned in a separate case last year. “I mean, it’s almost malpractice not to think about it.”

“All the old rules,” added Daniel McGuinness, one of Mr. Castillero’s defense lawyers, “are out the window.”

Mr. McGuinness said he used to discourage clients who raised the idea of a pardon by explaining the near impossibility of obtaining one.

“But in the world we live in now,” Mr. McGuinness said, “that’s not the case. Pardons are being granted to people before they’re charged, before they’re sentenced, while they’re in prison — it’s the Wild West out there.”

Even so, the case of Mr. Castillero, 48, stands out for how his aggressive courting of Mr. Trump in pursing a pardon ultimately complicated his efforts to obtain a lesser sentence.

A wide-ranging scheme

Mr. Castillero and two associates were indicted in November 2023 on securities fraud, conspiracy and other charges, announced in Manhattan by the U.S. attorney for New York’s Southern District, then a Biden appointee.

Mr. Castillero and one co-defendant were also charged with obstruction of justice; prosecutors said they deleted emails subpoenaed by the S.E.C. in its investigation of the defendants and their company, StraightPath Venture Partners.

The indictment charged that Mr. Castillero and his co-defendants used a large network of referral agents and “boiler-room”-style call centers to solicit investment in privately held companies that were expected to go public.

Although StraightPath claimed it charged no upfront fees, prosecutors said the defendants solicited funds from at least 2,000 investors, secretly marking up prices and diverting $75 million to themselves. Some of the money, the government said, went to buy luxury cars and boats, jewelry and Rolex watches.

The prosecution continued after Mr. Trump took office in January 2025 and after he installed Jay Clayton as the Southern District U.S. attorney.

At one point, Mr. Castillero considered cooperating with the government, court filings show. He and a lawyer met with prosecutors in so-called proffer sessions in which statements he made generally could not be used against him. At the meetings, he made incriminating statements, the filings say.

Mr. Castillero eventually dropped plans to cooperate, obtained new lawyers and went to trial.

As the 11-day proceeding wound to a close, a prosecutor, Allison Nichols, said in her closing argument, “StraightPath was built on lies — lies to regulators, lies to investors cold called out of the blue, and lies to StraightPath’s own clients.”

Mr. Castillero’s lawyer, Mr. McGuinness, told the jury there was no evidence his client knew there was a subpoena when he deleted emails, and argued that the government failed to show Mr. Castillero lied to investors.

“There’s not a shred of evidence at this trial that Mike did that,” Mr. McGuinness said.

The jury found Mr. Castillero and his co-defendants guilty on all counts. In a news release, Mr. Clayton, the U.S. attorney, said he commended “the career prosecutors and law enforcement agents for their work to protect investors in this important marketplace.”

The president’s friend

Mr. Castillero told The New York Times that he initially filed for a pardon on his own last summer, even before his trial began. He later retained Mr. Ticktin, who filed a more complete application after his conviction.

Mr. Ticktin, in a separate interview, said he has been a friend of Mr. Trump’s since they attended New York Military Academy together. He said that he had handled other pardon applications, including for Mr. Castillero’s co-defendants, and that he was doing so “because this is one that just needs to be pushed — these people are innocent people.”

He provided The Times with a copy of his cover letter to Mr. Trump as part of Mr. Castillero’s pardon application. In it, Mr. Ticktin asserts StraightPath was upfront and transparent and disclosed price markups, which he said were set fairly.

He blames “a few of the company’s lower-level brokers” for advising some customers without the defendants’ knowledge that the firm took no payments. “This discrepancy fueled the investigation and charges,” Mr. Ticktin wrote.

Mr. Ticktin also offered a rationale for why the U.S. attorney’s office and the S.E.C., now under Mr. Trump, continued to pursue his client.

“Mr. Castillero’s support for you,” Mr. Ticktin wrote, “has made him a target of the Biden lawfare machine, which continues to operate within the S.E.C., and of the Southern District of New York.”

Mr. Ticktin described the Southern District as “infamous” and “a court known for its opposition to MAGA.”

Mr. Ticktin cited the two Southern District judges involved in Mr. Castillero’s cases who had also overseen the matters that had drawn Mr. Trump’s ire.

And he added that given the “huge amount of ongoing work” by Southern District prosecutors, “it is not possible for any U.S. attorney to immediately purge all the Biden hires and still maintain the caseload in the courts.”

After his conviction, Mr. Castillero began to seek out media outlets where he could make his case publicly, in hopes of winning the president’s attention.

“I was trying to reach an audience of one,” Mr. Castillero said.

He said he made about a dozen appearances on programs, including “The Truth with John Gordon” and “Battlefront: Frontline with Dustin Faulkner.”

“They did it to me just because of my beliefs,” he said on another show, “Cowboy Logic.”

He added, “I believe the 2020 election was stolen. I’ve been very vocal.”

Appearing with the pro-Trump influencers Diamond & Silk, Mr. Castillero said no one was hurt by his scheme.

“There’s no victim,” he said. “Me and my two business partners, I guess.”

‘It has ruined his final days’

At Mr. Castillero’s sentencing on May 20, Lauren Galit, the daughter of one of StraightPath’s thousands of victims, addressed Judge Furman, describing how the fraud had devastated her nearly 90-year-father, a physician she described as smart but not fiscally savvy.

She and her family had tried endlessly to resurrect what was left of his finances, she said. He even had to cut back on birthday presents to his eight grandchildren.

“I have such anger, I cannot tell you,” Ms. Galit said. “It has ruined his final days.”

The government and Mr. Castillero’s lawyers had already weighed in with memos to the judge detailing their positions on his sentence. Prosecutors, citing Mr. Castillero’s media appearances, argued he had “gone on a press tour claiming he is the true victim of a ‘weaponized’ prosecution that targeted him for his political beliefs.”

“This is, as goes without saying, false,” the government wrote.

Mr. Castillero’s lawyers, Mr. McGuinness and Tess Cohen, asked Judge Furman for leniency, arguing that their client had been sloppy and made judgment errors but never set out to engineer a theft scheme. They also defended his claim he was targeted for supporting Mr. Trump, saying he was merely echoing a belief about the Biden Justice Department that Mr. Trump himself had repeatedly expressed.

When Judge Furman spoke, he said a substantial sentence was warranted. He said the evidence showed there had been “a massive fraud” that duped thousands of investors, many of them older and lacking sophistication in the financial markets. He said the defendants had “pursued wealth at all costs.”

Addressing Mr. Castillero, the judge said, “So the record is clear, I don’t care about your politics.” Mr. Castillero, he said, was free to speak publicly about his case.

He said he would also not impose harsher punishment on Mr. Castillero because he spoke his mind or campaigned for a pardon — “as craven and distasteful as that campaign appears to me.”

At the same time, Judge Furman said, he could plainly consider what he described as “an utter lack of acceptance of responsibility or expressions of remorse.”

And he said he saw “no facts whatsoever to support” Mr. Castillero’s assertion he was prosecuted for his political views.

He noted Mr. Castillero was tried under Mr. Clayton, “the president’s own handpicked U.S. attorney,” who issued a news release “trumpeting that conviction and praising the jury’s verdict.”

Most important, the judge said, given Mr. Castillero’s admissions at his proffer sessions, “it is a little hard to accept the claims that he is now making about why he was prosecuted in this case.”

Mr. Castillero was sentenced to 11 years in prison — as prosecutors recommended. His co-defendants received eight- and 10-year terms. Each was ordered to pay $140 million in restitution and forfeiture and to surrender to the authorities on Sept. 10. They are appealing their convictions.

On July 1, prosecutors wrote to Judge Furman, saying the Justice Department’s pardon attorney had asked if he wanted to offer comments on Mr. Castillero’s pardon application.

The judge, releasing the letter, said in an order that he had expressed his views at the sentencing and directed prosecutors to forward a transcript to the pardon office.

Beyond that, the judge added, he would “not express any views.”

Nicole Hong and Kenneth P. Vogel contributed reporting. Alain Delaquérière contributed research.