Baseball's fascinating new rivalry

Scott Boras has negotiated more than $5 billion in major league contracts and built a baseball agency that's the paragon of the industry. He has coined the phrases "iconic player" and "pillow contract," helped revolutionize the draft, and declined invitations to appear on the HBO Show "Arli$$" because it perpetuated so many negative stereotypes about the profession he holds dear.

He has been compared to Superman arch-enemy Lex Luthor and Star Wars villain Darth Vader while setting records in increments of tens of millions. Boras has even lectured at Harvard, a heady experience for a kid who grew up riding a tractor on the family farm before attending the University of the Pacific. Once Boras completed his talk to Harvard Law School students, they waited patiently in line to shake his hand and get career advice.

"I told them, 'I could never get into Harvard, and now that I'm here, I can't get out,'" Boras said, laughing.

But Boras never had reason to consider himself a pop culture icon until two events earlier this year. One day friends and clients called to inform him that he had been the answer to a question on the game show "Jeopardy." And then, in July, his name appeared in a tune by rapper Shawn Carter, aka Jay Z. The song "Crown," on the CD "Magna Carta Holy Grail," includes the following lyric:

"Scott Boras, you over baby
"Robinson Cano, you coming with me."

In April, Cano dropped a big one, revealing that he had left Boras and would be represented in his baseball dealings by Creative Artists Agency and in his off-field endeavors by Carter's Roc Nation sports. Baseball players change agents as routinely as walk-up music, but this transition was more hefty than most. Cano, 31, is a five-time All-Star with a .309 career batting average and more doubles (375) than Mickey Mantle amassed in his entire career with the Yankees. With Derek Jeter approaching 40 and Alex Rodriguez disgraced and also nearing the end, Cano could be the face for Major League Baseball's most storied franchise moving forward.

Cano's next big career step will come under the guidance of rapper and entrepreneur Jay Z, who is branching out into the athletic realm as a certified agent with the NBA and MLB. His small-yet-imposing clientele includes Oklahoma City Thunder forward Kevin Durant, WNBA Tulsa Shock guard Skylar Diggins, and New York Giants wide receiver Victor Cruz and New York Jets quarterback Geno Smith.

Jay Z's shot across Boras' bow set up a fascinating dynamic. On the one hand, you have the hard-driving baseball brand name who has skillfully helped owners part with their money since the Ronald Reagan administration. On the other, there's the music industry powerhouse with a flair for turning everything he touches to gold -- or platinum.

"It's certainly the clash of the titans," said Bob Boland, academic chair for New York University's Tisch Center of sports management. "This isn't just somebody going into the agent business or opening up an agent shop. This is somebody challenging the biggest guy on the street, Scott Boras, in his wheelhouse model.

"People perceive the agent business as a license to print money, but Boras is incredibly successful because he has clients who are in demand and he brings a lot of skill to it. It's not a business just anybody can enter and have enormous success in. He is where he is today because of a 30-year arc of work. He's the biggest target of Jay Z because it's getting those high-level talents that Jay Z [desires] the most."

Although Boras declines to comment on Cano or Jay Z directly, he will expound at length on the demands of the profession and his own credentials as a former professional player and attorney who has invested more than $150 million in his business. He spends a lot of time on the road watching baseball games and eating fast food, and has built a data-base so chock-full of information that he needs to house it in a 50-degree room to keep it cool. Boras believes that representing major league players requires a degree of training and expertise that are best acquired through complete immersion.

"I live what I talk." Boras said. "Our philosophy as a company is, 'We are 24/7 baseball.' Everything we do is related to a player's performance, durability and commitment to his team and his career. Every owner knows me. They can call me at night and know I'm not talking to a hockey, basketball player or football player. I want to be able to sit with owners and general managers and say, 'My life is your life -- total commitment to one game.' This is all we do."

Where does that leave Jay Z or anybody else who might view athlete representation as a vanity project or a sidelight to another profession? Feel free to draw your own conclusions.

"If Steven Spielberg walked into USC Medical Center and said, 'I want to do neurosurgery,' they don't give him a scalpel," Boras said.

A burgeoning force?

Through his Roc Nation media representatives, Jay Z declined to comment for this story. The agents at CAA also declined requests to talk, referring ESPN.com to statements made during the initial announcement of a partnership with Jay Z. In an interview with MLB.com in April, CAA's Brodie Van Wagenen, a former Stanford player who has been hailed as an up-and-comer in the industry, called the alliance with Roc Nation a "true collaboration" and said Jay Z would be "critically involved" in Cano's contract negotiations.

CAA is a formidable group in its own right, with a multitude of services to provide and one of the most star-studded clienteles in baseball. But the firm has made its biggest mark in negotiating contract extensions for players before they reach free agency rather than players on the open market. CAA's list of franchise mainstays includes San Francisco Giants catcher Buster Posey ($167 million) and pitcher Matt Cain ($127.5 million), Milwaukee Brewers outfielder Ryan Braun ($105 million), Washington Nationals third baseman Ryan Zimmerman ($100 million), Baltimore Orioles outfielder Adam Jones ($85.5 million) and Los Angeles Dodgers outfielder Andre Ethier ($85 million).

Van Wagenen will ostensibly be on the front lines doing the dance and exchanging figures with team executives on Cano, but the internal dynamics of the partnership remain a mystery. Will Jay Z keep tabs on every step in the process or swoop in at the end? Will he give his opinion as part of a collaborative effort, or be the one calling the shots? And how much input will Jay Z receive from Roc Nation president Juan Perez or Rich Kleiman, who have also been certified as baseball agents by the players association?

Jay Z has already exerted his influence by getting athletes in the door and dazzling them with personal attention upon arrival. In May, he gave Diggins a Mercedes-Benz as a gift upon her graduation from Notre Dame. And he recently made news for hosting an elaborate birthday bash for Cano in Antwerp, Belgium, during which multiple bottles of Armand de Brignac Ace of Spades champagne were consumed. When Cano received a $33,900 watch as part of the festivities, it sent out alarm bells among other agents and the people at the players association who drew up the game's agent regulations.

The glitz and glam notwithstanding, it would be a mistake to underestimate Jay Z's vision or brilliance as a businessman. He has sold about 50 million albums worldwide, won 17 Grammy Awards and has an estimated net worth of about $500 million.

"This guy is mega-wealthy and uber-successful," said a prominent baseball agent who asked not to be named. "He's probably negotiated his own deals with record executives who are more cut-throat than any GM of a baseball team. You want to talk about big business -- that's big business.

"This isn't rocket science. The guys at CAA have put a ton of time into it and know every variable in every contract constructed. They have that template laid. Sure, there are certain nuances in negotiating in this environment, and Jay Z has none of them, but I don't think he's going to have any problem getting his phone calls returned."

For baseball writers and club executives who might be wondering, Jay Z's schedule appears to preclude him from attending MLB's annual winter meetings in Orlando, Fla., in December. He'll be in Los Angeles, Fresno and San Jose, Calif., on his "Magna Carta World Tour" that week, so the chances of him renting out a suite at the Walt Disney World Swan and Dolphin resort and making a surprise appearance with his wife, Beyonce, are remote.

Endorsement magnet?

The stakes are huge for Cano. Sources said that he was seeking a 10-year, $310 million deal over the summer, while the Yankees are thinking more along the lines of Joe Mauer's eight-year, $184 million contract with the Minnesota Twins. That's a significant spread, and while the money will seem enormous to the general public either way, rest assured that competing agents will take note if Jay Z comes up short of expectations.

"I see eight years and $200 million as the biggest contract you could imagine [for Cano]," Boland said. "But the opposing agents are going to spin to every client they have that anything less than a $300 million figure is a failure. And they'll do it rather gleefully, I expect."

Cano, whose switch to Jay Z was predicated in part on enhancing his endorsement opportunities off the field, has already landed a national marketing deal with Pepsi under his new representatives. But the overall landscape for baseball players suggests his future opportunities will be limited. The 2013 list of the Forbes 100 wealthiest athletes included 27 baseball players ranging from A (Adrian Gonzalez) to Z (Barry Zito). They earned a combined total of $564 million in salary last year and $28 million in endorsements, with Jeter and Ichiro Suzuki accounting for about $15 million of that total.

Kobe Bryant, in contrast, made $28 million in salary and $34 million in endorsements, while LeBron James earned $18 million in salary from the Miami Heat and $42 million in outside income. While Mike Trout, Bryce Harper and some of baseball's young stars have definite potential as pitchmen, the daily grind of the sport and aging demographic of baseball fans seem to contradict the notion that Cano can hit the mother lode as an endorsement commodity.

Boras, whose company has a marketing arm that negotiated a national TV deal for Harper with GEICO, said the demands of the baseball season make it imperative that players put their priorities in order.

"Marketing is completely different in baseball than if you're a model or a musician or even a basketball or football player," Boras said. "It requires tremendous knowledge of the industry and the player to do this correctly. If you don't do it correctly, anything you make in marketing will serve as a loss of hundreds of millions in what a player can earn contractually."

In other words, if Robinson Cano is so worn out from chasing endorsements that he hits .240, Madison Avenue will lose interest very quickly. The baseball season is such a grind, a lot of players don't have the appetite for day-long photo shoots in January. They'd rather spend free winter days sitting in a duck blind, or playing golf, or making up for lost time with their families.

"I have four kids, and I'm really not interested in [endorsements]," said St. Louis Cardinals outfielder Matt Holliday, a Boras client since 2005. "Scott has a great marketing team and they tell you they can get you some side money, but the one thing he stresses is, 'You can make a ton of money as a great baseball player, so worry about being the best player you can be.' They don't necessarily want their clients flying around the country doing commercials in the offseason. That's a great opportunity to work on your game and your body to make sure you're ready to endure 162 games at the highest level."

Not quite "over"

The Jay Z incursion notwithstanding, Boras' clientele runs the gamut from high-profile stars to hot prospects on the rise. Prince Fielder has a $214 million deal with Detroit, and Holliday, Washington Nationals outfielder Jayson Werth and Texas shortstop Elvis Andrus are all in the nine-figure club. At the other end of the spectrum, Boras represents Mark Appel, Kris Bryant and other first-round picks working their way through the minors.

Between those two extremes lies an array of talent to keep Boras rolling in revenues well into the 2020s. He represents Matt Harvey, Stephen Strasburg, Jose Fernandez, Harper, Carlos Gonzalez, Chris Davis, Gerrit Cole, Hyun-Jin Ryu, Max Scherzer, Jacoby Ellsbury, Shin-Soo Choo, Domonic Brown, Eric Hosmer, Mike Moustakas, Matt Wieters, Carlos Gomez, Trevor Rosenthal, Austin Jackson, Pedro Alvarez and Nolan Arenado, among numerous others.

Jay Z's favorite target might be a lot of things. But "over" isn't one of them.

Boras is, nevertheless, old school. Even front office people who might roll their eyes at his economic sermons don't question his preparation or willingness to get in his players' faces and challenge them if they refuse to commit to their craft.

Some players eventually fall out of love with Boras, for a variety of reasons. Maybe he pushed the envelope while waiting for a February deal that failed to materialize. Or a player who isn't necessarily a star might have his phone calls returned by one of Boras' lieutenants rather than the man in charge. There's a joke in some front offices that Boras' lower-level clients get demoted to the "Mike Fischlin division," in reference to one of the other agents in his firm.

Mark Teixeira, who left the Boras group in 2011 three years after Boras landed him a $180 million contract with the Yankees, addressed Cano's decision to go with CAA and Roc Nation in an interview with the New York Daily News in April.

"Everyone knows Scott likes to control everything," Teixeira said. "He has a financial services part of his business, he has a sports performance side of his business, he has a mental performance side of his business. Everything that you could possibly do, he takes care of it for you -- if you choose. It doesn't necessarily benefit every player. Some guys need that and some guys want that, but the guys that want to take control of their own lives and make their own decisions, it's not ideal for."

Nevertheless, many of Boras' long-term clients swear by him and his attention to detail. He has two sports training institutes, sports psychologists on staff and several trusted aides -- most notably Jeff Musselman, Scott Chiamparino, Fischlin and Mike Fiore -- who graduated from playing to the agent business and have been with his group for years.

Two Boras clients, Holliday and Alvarez, spoke to ESPN.com at length about the impact that Boras has had on their careers, and tried to debunk certain widely held notions about Boras and his approach.

Misconception No. 1: It's only about the money.

Holliday recalled an encounter with Boras during a trip to Los Angeles in late May. He was hitting a respectable .270 with six home runs, but felt out-of-sorts and uncomfortable with his swing and his approach. Boras arrived at dinner with notes from previous conversations with Holliday and reams of data that showed how Holliday fared when he expanded his strike zone and swung at balls off the inside corner of the plate. At heart, Boras is a baseball dweeb who loves to talk about "bat drag" and "swing planes" as much as franchise values and the ramifications of the luxury tax.

"I think there's a misconception that Scott just loves to do these huge contracts and stick it to the owners," Holliday said. "His passion, and what he really enjoys, is the more hands-on, one-on-one, 'Let's get down and figure out a way for you to have the best possible career for as long as you can' conversation. He'll text me in the middle of the night and I'll be thinking, 'Why doesn't he sleep?' His mind is spinning, all the time."

Misconception No. 2: Boras has a Svengali-like hold on his players, and they essentially work for him instead of the other way around. It's perpetuated by stories from general managers who wonder if their offers to free agents were fully conveyed, or scouting directors who want to talk directly with elite draft picks only to find that they've mysteriously changed their cell phone numbers.

There's no question Boras drives the train more than most agents. But Holliday, who signed a $120 million deal with St. Louis in 2010, said he called the shots throughout the process while Boras constantly updated him on his options.

"I pay Scott to work for me and my family," Holliday said. "I think most of the time, the player chooses the most money. But for people to assume that Scott is just pushing players to the highest contract and not giving them any other options seems sort of ridiculous to me.

"There were a couple of cities where I told Scott, 'I don't want to go there.' We battled and I warned him, 'I will wring your neck.' People lose sight of the fact that the player makes his own decisions. This is your own life and your career, and you have to live it."

Alvarez, selected No. 2 overall by Pittsburgh out of Vanderbilt in the 2008 draft, didn't sign until August of that year and took some PR hits for being greedy or self-entitled. Despite the collateral damage, he reflects on his experience and says he was "100 percent in control" of his destiny and developed complete faith and trust in Boras' judgments.

Some scouts and executives roll their eyes when Boras, a former minor league second baseman with the Cardinals and Cubs, goes into his "I played the game" speech. But it's resonated with Alvarez.

"He has ex-players working for him who know what it's like to go hitless for two weeks," Alvarez said. "They know what it's like to not be able to throw a strike or execute a pitch whenever they want. That familiarity to relate to the player is huge.

"It's one of the intangibles they have to offer. When you talk to people in the company who have played and tell them about your feelings or your anguish or whatever, you know there's a person on the other end of the line who's gone through the same thing you're going through. And you know what? They'll probably have a pretty good answer for you."

The Big Deal awaits

The dynamics of Cano's free-agent adventure will play out over the coming weeks. Initially, media observers predicted that Cano's agent switch would facilitate a return to New York because CAA and Roc Nation would be much more amenable than Boras to signing an extension. Seven months later, Cano has hit the open market, and a new set of questions have arisen.

Did Jay Z and his group reduce Cano's leverage by making it so eminently clear that he wants to stay in New York to take advantage of his marketing opportunities? And if the Yankees have no reason to believe Cano would be interested in playing for the Rangers, Orioles or some other club, why shouldn't they hold the line and invest the cash they save on Cano in Japanese pitching sensation Masahiro Tanaka or free agent outfielder Carlos Beltran?

If the Yankees are sweating the possibility of Cano going elsewhere, they're doing a good job concealing it. In an interview with Bloomberg Television in September, team president Randy Levine made it clear there are limits to what the team is willing to spend on Cano or anybody else.

"Nobody is a 're-sign at all costs,'" Levine said.

Cano's upcoming deal has big ramifications for the Yankees, future marquee free agents and the men who negotiate their deals. If Jay Z hits paydirt, it could be a foothold to more Robinson Canos down the road. If Cano's deal is light, he'll have some proving to do within the industry.

Boras, meanwhile, is viewed in a whole new light by some of his players since the release of "Crown."

"I called him and said, 'You're in a rap song?' You finally made it," Holliday said.

When Boras drives to and from his office in Newport Beach, Calif., this winter, conversing with general managers about Ellsbury, Choo or Stephen Drew, he might pop in a CD of former Yankees outfielder Bernie Williams, a longtime client who has carved out a successful career as a jazz guitarist. Other than a little Luther Vandross here and Robin Thicke there, he concedes that his musical knowledge is relatively pedestrian.

Jay Z might be taking aim at his empire, but he plans to stay in his lane.

"I try to sing in the shower," Boras said. "And I'm bad."