NEW YORK » The all-night games were held in rarefied settings like a suite at the Plaza Hotel. One pink chip was worth $25,000. Masseuses were on hand to help relieve the tension, while the players were fueled by food and drink. And the stakes climbed into the stratosphere, with as much as $2 million on the table to be lost or won.

At one game, in an apartment in a glass condominium tower on Fifth Avenue, as cards fluttered and chips clattered across the table, its organizers suspected that a new player did not belong, though he had arrived with a regular. The two men were asked to leave. Turned out the organizers were right: The new player was an undercover FBI agent.

At roughly the same time, some of the people who helped organize the poker games were taking in breathtaking wagers on college and professional sports. One man bet $300,000 on last year’s Super Bowl — and lost. Another placed a $1 million wager on another sporting event.

The description of the poker games and the wagers were among the details found in hundreds of conversations and text messages secretly captured by the FBI, exposing the shadowy and illegal world of high-stakes gambling in New York City.

The recordings, according to court papers, were made over the last two years during an investigation into what federal authorities have characterized as two related multimillion-dollar money-laundering and gambling rings.

One of the gambling operations, which prosecutors say was led in part by the scion of a New York family that has wielded enormous power in the art market, with one of the largest collections of Impressionist and Modernist works in the world, was based in New York and Los Angeles, and served hedge fund titans, real estate magnates, celebrities and athletes.

The other, which prosecutors said was led by a Russian organized crime figure, catered to wealthy Russians living in Russia, Ukraine and elsewhere.

The scion of the New York family is Hillel Nahmad, 34, known as Helly, who was indicted in the case, along with 33 other people, on April 16; he is charged with racketeering, gambling and money laundering. He was released on bail.

The course of the investigation is detailed in hundreds of pages of wiretap and search-warrant affidavits.

Nahmad’s lawyers, Benjamin Brafman and Paul Shechtman, say their client has done nothing wrong. Brafman declined to discuss his client’s secretly recorded conversations, which included one in which he speaks of using the family’s art business as a cover to move around illicit money.

In it, Nahmad advises a woman to wire $150,000 to the bank account of his father, David (who was not charged), suggesting she lie about the reason, saying, "You just be like, Oh yeah, I bought a, you know, Picasso drawing or something."

Brafman said, "Itis a mistake to draw any negative inference orconclusion about a case or a particular defendant based on isolated taped conversations taken out of context." Among page after page of mundane conversations about gambling and recordings of Nahmad taking bets over his cellphone were glimpses of a strange world of greed, gamblers and two classes of bettors: Those who kept wagering and who, it seemed, never ran out of money; and those who kept wagering, though it seemed they had none.

Because several of the men accused of operating the gambling rings are related — a father, Vadim Trincher, and his two sons, Illya and Eugene — some of the wiretapped conversations have an oddly homespun feel to them, even as others revealed the thuggery and threats of violence some ring members used to pressure those who would not pay.

"Have the guy call my dad tmrw at 10 a.m. he will connect him to the guy in Moscow," Eugene Trincher tells another man in a text message. Another time, a defendant in the case sends Eugene a text about a money pickup in Las Vegas: "Ur dad still need me to pick up cash in lv?"

Another man wrote to Illya to tell him that his father was cleaning up at a poker game at the Plaza in the early hours of one January morning, saying "Your dad is eating people up." He added later: "Pops won a big pot this past half, don’t forget to remind him to tip the dealers, ha-ha!"

When Eugene Trincher picked up approximately $500,000 in cash from someone associated with an online gambling website, he brought it back to the family’s apartment in Trump Tower and his brother, speaking of the cash, later told their father:

"Dad, give it to Mom for a couple of days so she’ll give it to somebody else."

The affidavits, which are used by prosecutors to persuade judges to sign orders authorizing wiretaps and searches, contain details of the investigation and excerpts from conversations recorded pursuant to earlier eavesdropping orders.

When the New York Giants won the Super Bowl in 2012, a bettor identified in the affidavits only as "Tabor" won $600,000 from the Nahmad-Trincher organization. That set off a long series of seemingly fumbling exchanges about how to move such a large sum of money without tipping off the authorities.

"Tabor sent me his wire info, I might e-mail it to you, what’s your e-mail?" Helly Nahmad asked Illya Trincher on March 1. Trincher replied with a Hotmail address, but hastened to add that he had provided the wrong address. "Gmail, I mean gmail," Trincher said. The wire transfer apparently went through, but in April, Nahmad said that Tabor, fearing a trace, planned to send all the money back.

At that point, Nahmad may have revealed just how well-known the use of his father’s accounts had become. "He wants my Dad to pay him, not you, so just how my Dad had paid him before when we lost," Nahmad said.

The other end of the spectrum was one seemingly hapless bettor who was referred to as "NYU Dave" by the members of the gambling ring. In March, Trincher told another of the defendants, "NYU Dave keeps calling me. This retard owes me money, and I guess he owes you money too." Prosecutors say that as the man fell $1.2 million into debt, he tried to pay it off by signing over a share of his fashion company.

In April, NYU Dave sent what appear to be frantic text messages to Trincher, including "Giving you 10 percent of my company" and "Its worth 1.2 million." Apparently feeling the heat of his debt, the man added, "I need you to payoff a few people."

The affidavits also revealed what appears to be a grim cynicism among the defendants, especially when some unfortunate bettor’s life was collapsing under the weight of his gambling debts. In April, a man who appeared to be the owner of Titan Plumbing, Peter Skyllas, essentially signed his company over to the organization to save himself from over $2 million in losses. Illya Trincher joked to another member of the group that they had just gotten "some free plumbing work."

© 2013 The New York Times Company