On June 21, Judge Renee White of the New York State Supreme Court presented the defendant seated in front of her, Calvin Ramarro Darden Jr. with some decidedly unfavorable options: If he could come up with $5.7 million in restitution, the Manhattan District Attorney would consider a 6-18 year sentence in state prison; if he can only find $4 million, he could face up to 45 years.

Darden, a strapping 30-year-old with soft features and a sweet face sat almost motionless, turning to look only when someone entered or left the courtroom. Moments earlier, he’d looked bewildered and haggard as he was led into the courtroom in a brown button down shirt with yellow and orange vertical stripes and workaday baggy blue jeans. For a man who’d prided himself on wearing the finest name brand gear, showing up to court in clothes that looked slept-in was a step down. But no one could predict that a man with Darden’s pedigree would become a statistic of the criminal justice system.

For four years, Calvin Ramarro Darden Jr., investor of choice for Nelly, Latrell Sprewell and several other rappers and athletes, had the world by the balls. He pimped an invite-only American Express Centurion Card. He flew first class and traveled by limo when he touched down. At home, his garage housed an Infiniti SUV, Lamborghini Murcielago, Yamaha Motorcycle and a Mercedes-Benz CL600C coupe. Even his homes were name brand: the Legend and the Newswalk, an exclusive Brooklyn loft condo for when he was “working late.” He even left the blinds at his primary residence in Long Island open so folks in the complex could see how he was living, friends say. As the man who has long promoted this lifestyle might say, it looked like he was trying to keep up with the Combses.

But Darden’s high-flying life came crashing down on December 17, 2004, when the Manhattan District Attorney’s Office charged him in a 26-count indictment with grand larceny and related crimes. He faced 45 years. Eight months earlier, on April 14, 2004, Wachovia and Canadian mutual-fund giant AIC slapped him with a civil suit to recover the almost $4 million he owed the two companies. He now had something else in common with Combs: the high-profile Manhattan attorney Ben Brafman.
On April 26 at 4:11 p.m., paralegal Darryl Green pulled up to the impressive red brick sentry house at the Legend Beach and Yacht Club, a gated Long Island Sound community in Glen Cove, a New York suburb. He had a message for Darden, who lived behind the gate at 60 Pembroke Dr., a short walk from the indoor tennis courts, shore-side pool, private beach and his personal 50-foot boat slip.

Security intercepted Green at the gate. He hadn’t seen Darden in a month, the guard explained. Undeterred, Green returned on May 5. Darden was still M.I.A. so he fixed a subpoena to the door from Brad D. Rose, Cornell “Nelly” Haynes Jr.’s attorney. Nelly had invested $950,000 with Darden in June 2003 and the money was missing. Nelly wanted it repaid. But the multiplatinum rapper wasn’t the only one who had been taken for a ride.

Darden, who according to sources hooked prospective clients by telling them he managed Shaquille O’Neal’s money, also owed hip-hop producer Rockwilder close to half a million dollars and approximately $300,000 to Latrell Sprewell. But those debts seemed miniscule compared to his corporate debts: $632,000 to Wachovia Securities and almost $3.2 million to billionaire Michael Lee-Chin of AIC.
But Green was way too late. Once the site of lavish parties, 60 Pembroke¬—the complex’s largest home—now lay silent: The black reef sharks in the $350,000 aquarium had died; the home movie theatre was vacant. On April 20, Darden was forced to leave his Long Island waterfront home for a different waterfront residence: another gated community with water views and easy access to LaGuardia Airport, an important departure point for the jet setting Darden. But in his new community, Rikers Island, the guards are responsible for watching the residents, not the guests.

Darden isn’t sitting in Rikers for those alleged crimes, however, but for a smaller, victimless one: outstanding parking tickets on his 2003 Lamborghini Murcielago. He missed a court date on April 19. On April 20, the judge remanded him to state custody, where he waits for his lawyers and the DA to reach an equitable plea bargain. In any other case, being jailed on a parking violation might seem a little extreme. But Calvin Darden didn’t do anything halfway: in the course of whipping his Lambo around Manhattan, he’d had his license suspended or revoked on 17 separate occasions, and sometimes he just plain forgot to pay his car insurance.

Calvin Darden looked like a can’t-miss kid when he left Atlanta’s Morehouse. Groomed by the House’s well-regarded internship program, which emphasizes success in corporate America, he was a fine prospect to the Wall Street firms in need of diversity. Except that, according to a Morehouse spokesperson, “Mr. Darden apparently entered Morehouse in 1992, but he did not graduate.” (KING was unable to verify whether or not Darden falsified his education on his resume to land jobs at S-B, Wachovia and Merrill Lynch.)

Darden had the right pedigree: His father, Calvin Darden Sr., started his career as part-time deliveryman at United Parcel Service. Three decades later, he helmed their U.S. Operations. In 2002, Fortune named Darden Sr. the eighth-most powerful black executive, just ahead of Oprah. He retired this year but still sits on the board of directors of Coca-Cola Enterprises and Target. Fortunes shifted after UPS’s initial public offering in 1999. Cal Darden Sr. received shares that today have a total value of roughly $15 million.

In September 2001 he also signed up Nelly, who according to those familiar with their dealings, Darden met through Destiny Child’s Kelly Rowland. Darden’s relationship with Nelly, according to court documents, was copasetic the first couple of years.
By 2002, he began making serious inroads to the insular urban sports and music industry. Morehouse alums are prominent in the music and fashion industries, and though he had many allies in the business, his family ties proved more valuable. “With his dad being a high-ranking executive, you’re automatically thinking this guy must be special because the apple usually doesn’t fall too far from the tree,” says Troy Carter, one half of Erving Wonder, the company that steers the careers of Eve, Jadakiss and Styles P.

By most accounts, he was special. A charismatic man, he used his familiar face and his access to the right crowd to win the trust of otherwise smart, business-savvy stars.

It was an image that depended on a balancing act. In order to finance the high-flying lifestyle he felt necessary to lure clients, Darden became dangerously deceptive. In April 2003, court records show, Darden falsified his Smith Barney earnings, to receive a large signing bonus with Wachovia. He’d done the same thing, records show, when he left from Merrill Lynch in 2001. That same month, Wachovia gave him an advance of $632,448, a forgivable loan aimed at poaching what the company perceived as a big earner.

Darden seemed sexy to the major investment firms who valued his access to stars. A year earlier, he had become close with celebrity publicist Marvet Britto, who represented then Houston Rocket shooting guard Cuttino Mobley. Mobley, whose money was handled by Darden, asked Britto to introduce the broker to other top brass celebs.

To many of those prospective clients, Darden seemed impressive. “He came off as a really bright guy,” recalls Carter, who met Darden through Britto. Carter, generally “skeptical” of money managers, chose not to invest.

But Carter had extra reason to be skeptical of Darden. “Me and [Darden] had a few mutual friends,” says Carter. “It’s been his reputation since college that he would come up with these big stories. He was kind of known in school as a liar.”

But a few Britto clients, whom, Britto stresses, formed relationships with Darden on their own, did. Cheryl “Salt” James from Salt N Pepa was an early investor. She gave Darden an undisclosed sum that was later returned. Through her husband and manager Gavin Wray, she refused to comment citing the pending criminal case. Sprewell followed suit, investing $300,000, which has not been returned.

Darden also made contacts outside of Britto’s sphere, forming a friendship with Rockwilder, who became both a friend and client. “He got me for like a half [a million dollars],” Rockwilder explained during a brief telephone conversation. Rockwilder consented to a sit-down interview with KING but changed his mind after speaking with his lawyer.

Darden fancied himself more than a broker. He has several business ventures to show for it. He and David Gensler, a marketing whiz, became fast friends. Darden shopped around his pet project, a brand of African-American-themed condoms. He met with Steve Stoute, who reportedly dismissed the culturally sensitive prophylactics as an idea whose time had passed, say those familiar with the meetings.
The name “Black Umbrella” is also mentioned on Nelly and AIC’s lawsuits; Gensler describes it as a partnership between “him and James Prince from Rap-A-Lot Records. It was more a hybrid agent dealmaker kind of company. The plan was to do a lot of sports—manage boxers and cut branding and licensing deals with a lot of the sporting connections that Calvin and J Prince had.” Attempts to reach James Prince at his Rap-A-Lot offices were unsuccessful.
Nelly’s lawsuit is an important window into Darden’s modus operandi. In 2003, Nelly gave him $950,000 to invest in Tischman Speyer’s real estate investment trust (REIT), an investment fund run by one of Manhattan’s largest commercial landlords. With New York real estate values skyrocketing, it would have made a great investment. But court documents show Darden didn’t actually invest the money. Instead, he fabricated Black Umbrella receipt with the company’s name spelled “Spyer”, the suit says. The suit also shows Darden wasn’t the most organized hustler. The Black Umbrella receipt listed the investment at just $816,000.

Despite his growing web of deceptions, Darden could still charm and convince. “Every single person I knew jumped at the chance to meet Calvin, to work with Calvin, to introduce Calvin to 20 other people,” Gensler recalls.

Gensler, who partnered with Damon Dash to open a boutique branding company in 2003, was one of Darden’s strongest advocates. In the fall of 2003, he invited Darden to accompany him to work. He had someone he wanted Darden to meet. “We were sitting in a Rocawear showroom,” Gensler recalls. “Michael Lee-Chin was meeting with Damon. I was trying to introduce Calvin to Damon and I introduced all of them. I thought it would be good synergy.”

Lee-Chin had come from Jamaica to Canada for college. He’d stayed to build Canada’s largest mutual-fund company. AIC’s slogan preached restraint: “Buy. Hold. And Prosper.” But despite a personal net worth of $1.8 billion, Lee-Chin still had stars in his eyes. Like Darden, he wanted a slice of the burgeoning sports and entertainment pie. Two months before meeting Darden, Lee-Chin and Johnny Cochrane had attempted to start a sports agency/money management firm with Cochrane handling negotiations and Lee-Chin and AIC providing investment advice. They pursued LeBron James as their first client, but the venture never got off the ground.

As he had with previous employers, Darden misrepresented his Wachovia production to AIC. But this time, he took a wild swing for the fences. In order to secure the almost $3.2 million AIC signing bonus, Darden doctored documents to show he owed the money to Wachovia. He also claimed, court documents say, that Wachovia was holding his SEC registration until the money was repaid. The checks, he told Lee-Chin, should be made out to him, not Wachovia, since he’d already arranged to repay his former employer. On October 17, 2003, Lee-Chin wrote Darden two promissory notes for $1,592,761. Shortly thereafter, he wired almost $3.2 million into Darden’s personal bank account.
Darden set up an AIC office in Manhattan and became AIC’s Executive Manager, High Net Worth, a fitting title for someone who’d promised them Sam Jackson, Angela Bassett, Shaquile O’Neal, Latrell Sprewell, Glenn Rice, Tim Brown, Nelly, Star Jones and 21 high-ranking UPS execs, according to an AIC affidavit. But Darden only delivered his dad, who in fact never invested any money with AIC, the document says.
It took just six months for Darden and Lee-Chin’s relationship to sour. In that time, Darden spent a small fortune. He blew through $330,000 on his AmEx in three months. In March alone, he spent an astonishing $166,000 (see sidebar). On March 23, 2004, Lee-Chin fired Darden and demanded his money back. Darden claimed he didn’t have it. (Since Lee-Chin’s loan was originally based on fudged numbers, the civil suit appears to have a lot of merit.)

“Darden just said the relationship didn’t pan out,” Gensler says. “Something didn’t work out so there was confusion and animosity right away. I don’t know [the details]. All I know is you don’t piss off a billionaire.”

Lee-Chin, through AIC’s press office, declined comment. But a Canadian broker who’s steered clients towards AIC says Lee-Chin took the deception rather personally. “When you have made an unimaginable amount of money there is kind of an internal scorecard to make good decisions,” the broker says. “So when they get it wrong, [it hurts]. He led the legal process. Because he felt like this kind of situation, these things need to be stopped.”

The joint AIC-Wachovia lawsuit establishes a pattern of big-name promises, altered client statements and fuzzy math. There is even a Smith Barney affidavit detailing Darden’s number inflating while there. But the most compelling piece included in the suit is the handwritten mea culpa Darden sent Lee-Chin on September 9, 2004. “On a personal level,” he wrote, “I am sure that I have hurt your feelings, offended and embarrassed you . . . As far as mentors go, I couldn’t have picked two better ones than you and my dad. I am sorry that I didn’t take advantage of that in a positive way. I simply burned bridges. I am ashamed and embarrassed.”

Today, Calvin Ramarro Darden Jr.’s once promising career seems permanently grounded. He has also been excommunicated by the industry. His old Morehouse pal Farnsworth Bentley didn’t respond to repeated interview requests. Darden’s rim man, Will Castro, who’d just gotten wind of Darden’s incarceration, was more forthcoming. “We did a lot of business together,” he explained. “But I can’t fuck with [this interview].”

Gensler, who still considers Darden a close friend, says, “I’m not going to say he didn’t do something wrong just ’cause he’s a friend. But there are so many who absolutely used Calvin’s connections, money, power and influence to advance their own careers. As soon as something happened, they ghosted . . .Calvin became the devil.”
While Darden sits in Rikers, his life has come undone. The AIC/Wachovia suit is still pending, as is Nelly’s lawsuit. The federal government has also begun investigating his case, interviewing folks like Gensler. The speculation that they will soon bring charges is another reason that people aren’t talking.
A two-week timetable has been set to resolve Darden’s case. “He has a lot to think about between now and July 6,” Judge Renee White told the lawyers on June 21. “If it’s not deferred, we will move quickly to trial, because there is an 87-year-old victim.” This deadline should be easier to meet. If they don’t, the DA has seven additional victims ready to press a whole new set of charges.

All of Darden’s fast friends from his former life are gone. There are no celebrity supporters; even his father is absent. As he’s he led out of the courtroom for the bus back to Rikers, Calvin Ramarro Darden Jr. looks scared and vulnerable. The swagger is gone. The high life is just a memory.

[Published by King, July 2005]