Mr. Greenberg. (Getty Images)

Back in February, Josiah Boatswain, a 26-year-old from Flatbush, Brooklyn, and a few friends were pampering themselves at Fontainbleau: a $600-per-night resort that bills itself as the most luxurious hotel on the strip, promising high-end shopping, celebrities at every table, “24-7 glamour,” and an “expansive poolscape” on the stretch of Miami Beach known as Millionaire’s Row. Mr. Boatswain spent his vacation sipping Champagne, nibbling tiny chocolate cakes, and buying armfuls of couture, which he arranged in tableaux in his hotel room and photographed for his Facebook page.

In one picture, a silver wristwatch served as the understated centerpiece before a wall of Gucci and Salvatore Ferragamo boxes; another is simply a lineup of 11 shopping bags, like a Real Housewife’s walk-in closet. “My bro always want to do it big!” a friend commented approvingly.

According to the Manhattan District Attorney’s office, Mr. Boatswain, “Siah” or “Pepsi” to his friends, was financing his taste for Gucci and Moët with other people’s money, and not just any other people’s money, but that of billionaire investor Ira Rennert, former AIG chief Hank Greenberg’s Starr Foundation, and the Wasserman family trust, among other high-profile philanthropists, financiers and New York personalities. No fewer than 55 people were indicted and arraigned two weeks ago in a case the city and the police have dubbed “INSIDERS,” so named because low-level employees allegedly stole financial account information from patrons of four institutions, including about 150 donors to the United Jewish Appeal-Federation and about 900 customers of an Audi dealership in Coney Island. The case has not been tried and the proceedings will likely take more than a year. But according to the DA, the final victim list included Eric Zinterhofer, son-in-law to cosmetics heir Ron Lauder; Paula Sarnoff Oreck, the niece of former RCA head David Sarnoff and ex-wife of Oreck vacuum-cleaner big David Oreck; and, according to the New York Post, NBA commissioner David Stern.

Billionaires. Cyber crime. Insiders. Did the investigators realize they had a very sexy case right away? “Oh, yeah,” said Assistant District Attorney David Szuchman. “Very early on, when we realized there was an insider at UJA; we realized that the amount of information that was being compromised was large,” he said. “Then we realized that the group had to be working with others and it was a very, very large group to investigate. The fraud was so prolific.”

Basically, the cops were tipped off when the swindlers cashed one too many money orders. When you get access to a stolen debit card, one way to milk more cash out fast is to take it to the post office. With ATMs, you have withdrawal caps; money orders come in denominations of $1,000 and the fee is just $1.55.

Banks are hip to the money order racket, however. When debit cards that had been used to buy money orders were later flagged for fraud, the banks complained to the postal service. Mr. Szuchman couldn’t go into specifics, citing trade secrets of the cyber crime unit. But the gist is this: After the USPS saw about a dozen bogus money orders, mostly in Brooklyn and within a short time, the NYPD made a few arrests, which led to a search warrant for a cell phone or two, which led to the epiphany that the money orders were coming from high-profile philanthropists, which eventually led back to the UJA, where the investigators found their first “insider” in an elaborate plot that was as much a jackpot for the cops as it allegedly had been for the bad guys.

“We’re working a normal case and we’re going to handle it the same way either way,” Mr. Szuchman said. “But we were aware of some of the individuals that were named in the indictment as victims—we’re aware of the size of some of those donors.”

There are no signs, however, that Pepsi and his co-conspirators realized they were pilfering from the über-elite. The big-name victims are listed in the court filings alongside less fabulous surnames of unlucky doctors, lawyers and realtors. The thieves didn’t care if a particular UJA donor had ponied up $18 or a million-dollar check, as long as it was attached to a valid checking account number or credit card.

The alleged conspiracy appears to have been almost leaderless, and it’s still unclear who started the scheme. Most of the defendants are under 30, some have gang affiliations, and all but five are from Brooklyn. “It’s very hard for us to figure out who started it and when they started it,” Mr. Szuchman said. “We don’t really know.”

The list is an ethnic and demographic mix: a Polish bank teller, a 37-year-old Hispanic UPS worker, a 19-year-old from Florida. Five defendants are still unidentified, known just by their pseudonyms: “King Joffy,” “Michelle Brown,” “Paul None Livingston,” “Kevin None Rodriguez” and “Chuck.” The Post made much of the case’s alleged gang roots: “Street gangs target the charitable and rich,” the paper reported, but the defendants are associated variously with the Bloods, Crips and a hyperlocal East Flatbush gang called the Outlaws—suggesting it wasn’t an organized street crime operation, as gangs don’t typically collaborate. Two persons of interest turned up dead during the 18-month investigation, but there is no evidence that the murders were linked to the conspiracy or the investigation.

The main force behind the investigation, which involved multiple cell phone taps and subpoenas for text messages, was the District Attorney’s Cybercrime and Identity Theft Bureau, of which Mr. Szuchman is the chief. The former Eliot Spitzer acolyte took the job after a brief stint as head of the New Jersey State Division of Consumer Affairs under Jon Corzine. He now supervises a crack team of prosecutors, cyber-crime analysts and digital forensic analysts who snoop through confiscated iPads, smartphones and computers for a damning digital trail, things like the Google history of Justin Waller, a man who killed his roommate last year and reportedly searched, “How long does it take for a dead body to smell?”

“Cyber crime” generally calls to mind a cunning geek in a Guy Fawkes mask, typing out the recipe for a dangerous virus or phishing up Bank of America passwords from his parents’ basement. The perpetrators of the INSIDERS case had no such savvy (and indeed, neglected to make their Facebook photos private).

“This is a cyber crime because of the way the crimes were committed,” Mr. Szuchman said in an email. “BlackBerrys and smartphones were key components to committing the crimes from communicating to trafficking the personal identifying information.”

Even so, the investigators were arguably the ones doing most of the cybering. Investigators eavesdropped on the suspects’ phone calls, read their text messages and of course peeked at their social media profiles (with a bag of popcorn, we imagine, based on portraits of Pepsi pouring bottles of Champagne and liquor onto the floor at a night club). The indictment even cites emails the conspirators sent each other with credit card account numbers. “It’s a strong case,” Mr. Szuchman said.

Pepsi was one of seven accused “buyers,” who paid for the stolen personal data, then used it or resold it. These buyers, with nicknames like “Gucci,” “Chin,” “Tugs” and “Tigga,” tied together what would otherwise have been a set of similar but disconnected crimes.

The other commonality was the source of the credit information: lowly employees at institutions who happened to have access to the finances of strangers.

One of the reputed four key “insiders” was Tracey Nelson, a 24-year-old who pushed papers at the UJA. Ms. Nelson snapped pictures of donor information with her BlackBerry or simply walked out with papers in her purse; she sobbed openly during her arraignment.

Glenn Abolafia is the court-appointed attorney for Ms. Nelson, who pleaded not guilty. “We’re just at the beginning of the case and there is a lot of investigation to do to see if any of the accusations make any sense,” he said.

Ms. Nelson’s live-in boyfriend, Robbie Millar, 26, worked at Audi and was “a big player,” according to the DA. The other two, smaller fries, were Nicola Bennett, a pretty 30-year-old employee of residential property manager AKAM Associates, and Karen Chance, a 32-year-old teller at Chase Bank at 36th Street and Seventh Avenue.

The DA has divided the conspiracy by roles: insiders, identity buyers, accomplice recruiters, check-makers and collusive account holders. The thieves had to get access to a bank account or credit card information and then cash out as fast as possible before the account was flagged for suspicious activity. Therefore, some conspirators allegedly printed fake checks at home and forged signatures. Other defendants cashed counterfeit checks and accepted fraudulent transfers through their own legitimate bank accounts from sources that, to any observer, would seem incredibly unlikely. In a typical transaction from the indictment, an unnamed conspirator used a debit card belonging to a defendant to deposit a fake check for $9,536 from hedge fund Paulson & Co. on June 18, 2010. The American Institute of Certified Public Accountants paid out $2,769 to defendant Cassilda Mitchell via a counterfeit check; defendant Nicole Leach Vitalis received a phony $9,000 bank transfer from viral marketing company Oddcast. The crew also bought electronics and other big-ticket items, which they got cash for from their 33-year-old fence, Younis Abidar, who sold them on the black market.

Others like the appropriately named “Treasure,” one 25-year-old Umar Credle, cashed USPS money orders, the practice that eventually got the ring busted.

Insiders stealing identities got hundreds of dollars per account, although rates varied. Chase accounts could fetch a higher price because the ring had at least three insiders working behind the counter who ensured the fraud didn’t set off internal alarms. Collusive bank account holders got perhaps a $100 or $200 cut per transaction.

In the end, Mr. Greenberg, Mr. Rennert, Ms. Oreck and the estimated 200 or so victims were reimbursed by the banks for their losses. “The Manhattan DA’s office informed us that this type of breach can happen in any organization, no matter how stringent its controls,” UJA said in a statement issued after the indictment; the organization declined to elaborate beyond its press release to The Observer. Calls to Open Road Audi were not returned.

The 55 defendants are being charged with various degrees of conspiracy, possession of stolen property, grand larceny and identity theft. As the DA tells it, JP Morgan Chase, TD Bank, Citibank, Discover and American Express took the hit for the $2 million or so that paid for flights, movie tickets and electronics and kept the defendants in Louis Vuitton and Yves Saint Laurent. Prosecutors say they have stacks of evidence against the accused, whose first pretrial hearings are scheduled for February. If convicted, at least they got to do it big for a while.

Highlights:

• Derek Jeter nicknamed the kid "Squeegee." Because Mr. Jeter thought said batboy looked like a Squeegee.
• Mr. Jeter used to greet the batboys as "bee-yotch-es."
• When Bill Clinton dropped by the clubhouse, Mr. Jeter's only words for him were "Hey, Mr. President, you staying out of trouble?"
• Mr. Jeter sent his trainer to pick up women he was attracted to in bars, rather than initiate contact with them himself.
• Jorge Posada once tipped the batboy $7,000 at the end of the year. Alex Rodriguez? $1,400.
• Former Yankees manager Joe Torre used to bet on horses. From the dugout. During games.
• Whenever Yankees owner George Steinbrenner was in the house, the code used was "RED ALERT."

The most endearing tale, however, may be reserved for designated hitter and outfielder Hideki "Godzilla"  Matsui, the otherwise quiet and reliable 2009 World Series MVP, who the Yankees let go the next season on a one-year $6.5M contract to the Los Angeles Angels in a flub that still stings Yankees fans to this day. This wonderful anecdote about Mr. Matsui's mystique-shrouded clubhouse demeanor—which little was known about, as he was never much of a talker, even for the Yankees—may only serve to make Yankees fans miss him more.

The setting is a locker room meeting before Game 7 of the 2004 ACLS, which the Yankees lost to the Boston Red Sox, who went on to win the World Series. And, scene:

At the end of the meeting it was traditional for Joe Torre to ask Jorge Posada what we were going to do. He would reply, "Grind it!" This time -- I guess to make Hideki Matsui feel more part of the team -- Torre turned tohimat the end of the meeting.

"What are we going to do?"

Hideki paused for just a second before replying.

"Kick ass. Pop champagne. And get some ho's."

Reminder: Mr. Matsui emigrated from Japan to play for the New York Yankees in 2003. It took less than two seasons with the Yankees before he got to that point.

There is truly nothing in the world like a pinstriped baseball player of New York.

fkamer@observer.com | @weareyourfek

"Caleb hanie??" I wrote.

"Yeah," John texted back, "u know yur [screwed] when yur football team depends on a guy named caleb." (The actual word he used is one favored by Antonio Cromartie.)

Actually, they were screwed before the game even started. Their coach is Lovie Smith.

This is probably where I should state for the record that I have nothing against Lovie Smith. He has proven himself a capable NFL head coach, taking one decidedly unspectacular Bears team to this year's conference title game and another all the way to the Super Bowl. The problem with Lovie Smith, if you look at the evidence, is that his name is Lovie Smith.

Consider: Of the 90 teams that have now played in the Super Bowl (counting multiple-timers separately), only 10 have been coached by men with polysyllabic first names. (See the full chart.) The rest? Your usual Toms, Dicks, and Harrys—minus the Harrys, of course.

Good old-fashioned all-American appellations dominate the list, names like Hank, Chuck, and Weeb. (Weeb!) "Great strong simple names, suggesting a moral rigor," as DeLillo wrote in White Noise. That's Don DeLillo, by the way, as in Shula and McCafferty.

You don't find any Spencers or Aidens dressing down 330-pound nose tackles on Super Sunday. Name your boy John and he's got a shot at the NFL; name him Leonard and he's liable to end up with a Master's in Liberal Studies from Wesleyan. The list of Super Bowl coaches is filled with hardy, hearty, monosyllabic monikers. Vince and Joe, George and Sean, John and Jon.

Guys named Bill have won nine Super Bowls. That makes nine for Bills, none for the Bills. (Sorry, Buffalo fans.) Four different Mikes have won titles; on Sunday the Packers' McCarthy can become the fifth. (The Steelers' Mike Tomlin already won one.) Something's going on here. Right?

Much has been made of the NFL's culture of violence and machismo, especially in light of the recent awareness of the concussion crisis. In contrast to, say, baseball, where managers' names often tend toward the quirky (Sparky, Whitey, Dusty), football has always put a premium on authoritarian leadership and tough love. Bill Parcells, Tom Coughlin, Bill Belichick--these are your archetypical military-type leaders who managed to strike fear into enormous grown men. Football, as George Carlin famously pointed out, is like war, and in war you want your leader, your general, to be a strong, decisive, commanding presence. Imagine marching into battle behind a guy named Eustace. Thanks, but I'd prefer to leave my life in the hands of a Chuck.

Of the 27 coaches who have won Super Bowls, only one, Jimmy Johnson, went by the polysyllabic, more boyish-sounding, version of his name. And 19 of the 23 monosyllabic champions chose pithy nicknames (or a middle name, in the case of Sean Payton) over the ones they were born with. Chuck Noll instead of Charles. Tom Landry instead of Thomas. Admit it: "Michael Ditka" just doesn't have the same punch.

Bear in mind whom this is all coming from. Like millions of other American parents of the 1970s and '80s, mine named me Michael. But--and here's the kicker--my mother absolutely despised the name Mike. (Why she gave her only son a name with a nickname she hated remains a mystery to me.) From day one, I was to be called Michael, and nothing else.

When I was 13, I wanted to be an NFL coach when I grew up. Two decades later, I'm a writer with an MFA from a school that used to be an all-women's college.

This Sunday two other Michaels, now both Mikes, will lead their respective teams onto the field in Super Bowl XLV. One of them, the Steelers' Mike Tomlin, isn't even 40 years old. Let's face it, that could have been me out there. It doesn't matter that I've never played a day of organized football in my life, or that when I was 13, I barely weighed 100 pounds and ran cross-country.

I still blame my mom.

See our comprehensive chart of The Winningest Names in Football. >>

A trio of City Councilmen thinks New York should capitalize on the blockbuster-generated publicity wave coming soon so they have introduced a resolution designating New York City’s new nickname “Gotham City," just in time for the caped crusader to grace cinema screens across the country.

Queens Councilman and boyhood Batman fan Hiram Monserrate told The Village Voice blog Runnin Scared that the new nickname will lure tourists to visit the “real Gotham City and come visit our shops.”

“I see that as a marketing tool... taking advantage of this movie which will be one of those gate-breaking, record-selling movies like it always is,” he told the Voice.

Granted, there are a lot more friendly monikers that have been attached to New York over the years than the dark, foreboding Gotham City depicted in the Batman movies, but this one was the first and even “preceded the Big Apple,” according to the resolution.

The name Gotham was first applied to New York City in Washington Irving’s 1807 “Salmagundi Papers,” to draw a favorable comparison between New Yorkers and the shrewd inhabitants of Gotham, Nottinghamshire, England.

“For over the past six decades, New York City has served as the model for Gotham City, the imagined hometown of Batman and his civilian counterpart, Bruce Wayne,” the resolution states.

“Several New York City-based institutions have incorporated the 'Gotham' name into its title, including the Gotham Center for New York City History, the Gotham Gazette, Gotham Bar & Grill, Gotham Writer’s Workshop and Gotham Comedy Club…

“Whether it refers to the clever inhabitants of a distant land, or a fictitious city protected by the Caped Crusader, the name 'Gotham' will forever be inextricably linked with our great metropolis.”