Willie Cauley-Stein’s signing with Roc Nation Sports a perfect match—but will they last?

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By employing street-smart ethos, leveraging the agent pool from business partner CAA and choosing clients wisely, Jay Z may have another hit with Roc Nation Sports. But for how long?

By Andrew Pridgen

Roc Nation Sports this week signed former Kentucky standout center Willie Cauley-Stein; a plausible ping pong ball pick for the June 25 NBA draft and first overall center were it not for Duke freshman Jahlil Okafor declaring eligible.

Steady improvement landed Cauley-Stein on the 2015 All-SEC team, the 2015 All-SEC Defensive Team and the 2015 USA Today All-American Team. Coming out of high school, Cauley-Stein was good but not lottery material. He was ESPNU’s tenth-best prep center and the nation’s thirty-second-ranked overall high school prospect in 2012. NBA scouts like to see these kind of year-over-year gains.

Detractors say Cauley-Stein’s stock rose so dramatically this year because he was surrounded by six other equally worthy NBA prospects. And a willowy seven-footer who has tough time scoring head-to-head against physical centers (see: Frank Kaminsky) may soon find himself coming off the bench overseas.

He joins four professional basketball players at RNS including Kevin Durant and the WNBA’s Skylar Diggins. The incoming NBA rookie pushes the boutique firm’s client roster into the double-digit stratosphere (10).

The size and age of RNS belies the agency’s achievements. Since its founding in 2013, RNS has negotiated baseball’s biggest contract, non-pitcher category, along with basketball’s biggest shoe deal—ever. The shop, run by a pair of novices: a hip-hop star and his long-time right hand, seems to have a knack for choosing players with decent-guy images and potential career longevity.

A few of RNS’s wins over the last calendar year:

  • A 10-year deal with Nike for KD that could make him $300 million richer—not bad for a power forward whose career’s prime may be ushered out with the Obama administration. Durant’s RNS agents started a bidding war between Nike and Under Armour which pushed the incumbent to best its original offer by more than 50%.
  • A 6-year, $72.5 million contract for Cuban outfielder Rusney Castillo with the Boston Red Sox. This is the largest contract ever for a Cuban player. Castillo owing a debt of gratitude to the established talents of fellow defectors Yoenis Cespedis and Yasiel Puig.
  • A 10-year $240 million contract for Robinson Cano to pull a reverse Sleepless in Seattle and move from the Empire State to the Emerald City. The contract according to Sportrac ties Cano with Albert Pujols and Prince Fielder as the highest-paid position players in the game.
  • RNS advised Skyler Diggins to forego seven-figure deals to play in Europe, Asia or Russia during the WNBA offseason to supplant her $105k rookie contract. Instead, she signed with Sprint and Nike and started her own line of headbands. She appeared in the Sports Illustrated Swimsuit Issue and Vogue. By avoiding off-season injury overseas and marketing herself as a strong, relatable role model for athletes (especially girls), Diggins could become the league’s most-recognizable if not highest-paid.

The agency has also attracted wideouts Dez Bryant of the Cowboys, the Giants’ Victor Cruz and the Colts’ Hakeem Nicks as well as Jets QB Geeno Smith. Pittsburgh Steelers’ wideout Antonio Brown left RNS after just two months in 2014.

Currently there is a 50-employee roster at RNS, which puts its support-to-athlete ratio at about 5-to-1. Albeit much of the staff splits time with parent company Roc Nation, an entertainment agency which has about 110 artists from recording, film and TV. RNS president Juan Perez, 46, graduated high school on the Upper West Side and worked odd jobs before befriending Kareem Burke (now in prison for narcotics distribution) who co-founded Roc-A-Fella Records with Jay Z and Damon Dash in the mid-’90s.

Perez helped run ventures outside music with Jay Z—including turning the 40/40 Club into a once-robust but currently wilting chain of sports bars.

A successful sports agency run by a pair of former hustlers with a single high school diploma between them seems unlikely. But where they lack expertise, RNS has enlisted the council of industry veterans including agents Tom Condon and Brodie Van Wagenen who work for partner CAA’s sports division. It is Van Wagenen along with law firm Reed Smith (sound familiar? They represented and have been subsequently stiffed by Alex Rodriguez) which did the heavy lifting in the Cano and Castillo deals. Even so, Perez insists he and Jay Z are at the table for all contract dealings as he chest thumps the duo’s potential shakeup of the industry.

Which brings us to one-time hip-hop-mogul-turned-sports-agent Master P.

P’s No Limit Sports shocked the sporting world by negotiating the worst deal for a player in any sport in history. Ricky Williams, the 1999 NFL Draft’s number 5 overall pick, signed a contract to earn the league minimum base salary each season plus incentives and $5 million of his $8.8 million signing bonus was deferred.

The incentive bar was set so high Williams only attained one of 25 by his rookie season’s end. He earned $3.8 million that year to the $14.8 million of fellow rookie and lower pick Edgerrin James. New Orleans, which mortgaged its future before lowballing Williams, also lost. The Saints traded all of their remaining 1999 picks as well as the first- and third-round picks in 2000, eight in all, to get Williams. Those picks resulted in, among others, Pro Bowlers Champ Bailey and Lavar Arrington.

Williams eventually sprung himself from the deal and New Orleans, firing Master P, hiring Leigh Steinberg and packing flip flops for Miami. Master P filed for bankruptcy in 2011.

The emergence of Cauley-Stein during his last year in a Wildcat uniform as a pick-and-roll defender, a cagey passer and an emerging presence beneath the rim may be a good metaphor for RNS. The agency has shown early on it knows enough to know when to show flash and when to dish. But the question remains will Cauley-Stein’s and RNS’s emerging game be good enough for a long career? If history is to be believed, both will likely be out of the pros within a half-decade.

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