PORTLAND, Maine — A federal judge had to reconcile two sharply contrasting images of Saco lawyer and hockey agent Gary Prolman presented Tuesday before settling on a sentence for conspiring to launder drug money.

Ultimately, U.S. District Court Judge George Z. Singal said he didn’t buy Prolman’s story he was largely naive about the drug trafficking done by his client-turned-business partner.

Singal sentenced the now-suspended lawyer to two years in federal prison for one count of conspiracy to launder drug money. Prolman, 53, pleaded guilty to the charge in April.

“Mr. Prolman did not win all of his jury trials but four by being a dummy,” Singal said during the delivery of his sentence. “The backpacks, the bills, the refusal to deposit $10,000, the changing of money to larger denominations. Mr. Prolman is deluding himself if he thinks any reasonable person seeing those facts would believe he was a babe in the woods.”

But while prosecutor Daniel Perry from the U.S. attorney’s office characterized Prolman as a regular cocaine user and knowing conspirator with trafficker David Jones — who is awaiting sentencing on federal drug and laundering charges — Prolman and his supporters painted a more wholesome picture of the lawyer in court Tuesday.

Prolman told Singal he’s “embarrassed and remorseful” for his role in the scheme, and insisted he believed Jones made his money as an up-and-coming music industry entrepreneur, only realizing at the tail end of their relationship that the money he’d been handling was from illegal marijuana trafficking.

“He told me about selling a song for $300,000,” an emotional Prolman told Singal. “We had not talked about a marijuana distribution business or anything like that. … I have to be one of the stupidest people in the world to have not seen that. I wanted to believe his story.”

Dozens of people — including family members, friends and legal colleagues — wrote letters or testified in court in support of Prolman. They told Singal that Prolman was a selfless volunteer, taking on clients who couldn’t pay, coaching sports in the community and organizing countless charity events.

“It’s pretty rare to find somebody so willing to help who’s got so much on his plate,” said one longtime friend, Lee Goldberg, during court testimony Monday.

Earl Prolman, the defendant’s father, said his son accepted Jones’ money to help get a fledgling sports agency business established and simply didn’t “do enough homework” on Jones before accepting the investment.

“He made a mistake,” the elder Prolman told Singal, with four family members at his side. “He knows he made a mistake. He’s lost everything, especially his fine reputation.”

Assistant U.S. Attorney Perry acknowledged Prolman’s work in the community and agreed that Prolman took Jones’ money, in part, to help prop up his struggling sports agency startup.

But Perry argued the lawyer, who had previously been accepting cash from his father to keep his business afloat, knew very well where Jones made his money.

“It’s one thing to say this was a lapse in judgment, a terrible mistake, ignoring the red flags — that person can say he was victimized by David Jones,” Perry said. “What really happened here was Gary Prolman got involved with a drug dealer and saw an easy way to make his dreams come true.”

Prosecutors have argued Prolman handled a total of $177,500 in Jones’ marijuana trafficking revenues, breaking deposits up into amounts less than $10,000 to avoid federal reporting guidelines, and then investing the money in his sports agency business or a Saco property.

Perry called upon Jones to testify in the sentencing hearing Monday. The convicted trafficker, who is in custody awaiting a February sentencing date, said he made as much as $220,000 a month selling marijuana.

Jones, who admitted under cross-examination by Prolman’s attorney he would “do whatever he could” to benefit his own case, told the court he was referred to Prolman by their mutual drug dealer.

“I told [Prolman] I needed to clean some marijuana money,” Jones testified. “He told me he didn’t want to hear any more about where the money was coming from, but that he could set up some corporations.”

Future investments in Prolman’s ventures came in backpacks full of vacuum-sealed packets of cash, Perry told Singal.

“His actions, his lies [and] his misstatements to the bank all show his true motivations,” Perry said. “[His supporters who testified] were not aware of the Gary Prolman who was buying 8-balls of cocaine with his father’s money.”

Although Singal delivered a lighter sentence than the prosecution recommendation of 36 months — three years — in prison, he sided with Perry in sentiment, questioning Prolman during the hearing about what the judge considered several discrepancies in his testimony.

“I had to drag details and concessions out of him, which he knew I knew,” Singal told Prolman’s attorney, Peter DeTroy. “I think he was evasive throughout [the case], including today.”

DeTroy acknowledged that Prolman’s acceptance of responsibility in the case “came out haltingly” and “in pieces.”

“There are people who come to Jesus a lot quicker than others,” DeTroy told Singal.

Known in Cumberland and York counties as a criminal defense lawyer, Prolman was the only lawyer to get an accused john acquitted in last year’s high-profile Kennebunk Zumba prostitution case.

Prolman client and former Kennebunk High School hockey coach Donald Hill was the only one of 68 individuals charged with paying local Zumba fitness instructor Alexis Wright for sex to take his case to a jury trial and win acquittal.

Wright, Thomaston-based business partner Mark Strong and dozens of other johns were convicted for their roles in the scandalous case, which attracted worldwide media attention because of its setting in an otherwise quaint Maine town and widespread rumors about whether anyone famous might be revealed as one of Wright’s reported 140-plus clients.

Seth Koenig

Seth has nearly a decade of professional journalism experience and writes about the greater Portland region.