Ready to mix baseball with business?

Milwaukee pitcher Zack Greinke has a flair for innovation on the mound. He makes up pitches as he goes along, it's said. A little more than a year ago, when Greinke wanted out of Kansas City, reports surfaced that he was "bored" after nine seasons in the Royals' organization, and desperately in need of a fresh start both intellectually and emotionally.

Greinke's willingness to travel a different path also extends to his business dealings, where he's taking an unconventional approach as that rarest of baseball birds -- the contract do-it-yourselfer.

Greinke, the 2009 American League Cy Young Award winner, has created a bit of a stir of late. It began during the winter meetings with a report that Greinke had parted ways with his agents and is currently going sans representation. That's a noteworthy development because Greinke is eligible for free agency in November, and if Brewers general manager Doug Melvin wants to reach out and start a dialogue, the person he needs to engage is … well … Zack Greinke.

During the Brewers' fan festival last weekend, Greinke told Adam McCalvy of MLB.com that he's open to the idea of a contract extension. But until further notice, he is charting his own, commission-free course.

"It'd be me in charge as of right now," Greinke said. "So, we'll see how long that lasts."

Most fans are oblivious to the role of agents until Scott Boras is holding court at the winter meetings or sitting on the podium at the Prince Fielder news conference in Detroit. The team jersey is raised for photographers, the eye-popping numbers are reported, and Boras is inevitably blamed for everything from rising ticket prices to a rampant sense of entitlement among MLB players.

But agents serve as an important, ingrained cog in a player's maturation process. They negotiate draft signing bonuses as "advisers," help arrange baseball card and equipment deals for minor leaguers, spend countless hours preparing arbitration cases, and help players with their taxes, house-hunting and the million-and-one other life details that accompany new contracts. Established agents also serve as sounding boards and valued advisers when the MLB Players Association is negotiating a new labor agreement -- just the way Marvin Miller envisioned it back in the 1970s.

Free spirit

Luis Castillo, Jose Tabata and several other players have changed agents the way Cal Ripken Jr. used to change batting stances. Greinke, in contrast, is a monument to stability. In 2002, Mike Milchin and John Courtright of SFX helped him land a $2,475,000 signing bonus with Kansas City as the No. 6 pick in the draft. For the first eight years of Greinke's career, Courtright helped him navigate his issues with social anxiety disorder and supported him when he walked away from baseball for two months (and considered joining the professional golf tour) several years ago. Courtright also negotiated a four-year, $38 million extension for Greinke with Kansas City in January 2009.

Last winter, for reasons known only to Greinke, the relationship ran its course. Greinke left SFX for Creative Artists Agency, which helped facilitate a six-player trade between the Royals and Brewers in December 2010.

Greinke was affiliated with CAA for less than 60 days, and never signed the paperwork required to designate an agent for 2011. He simply opted to go without one last season. The buzz within the industry that Greinke "fired" CAA last spring appears to overstate the depth of the relationship.

Life in Milwaukee clearly agreed with Greinke. He posted a 16-6 record with a 3.83 ERA, led the majors with 10.54 strikeouts per nine innings, and quickly warmed to the idea of swinging a bat and running the bases in his new National League environs. He also lived up to his reputation as quirky and, at times, exasperating. Greinke missed several weeks after suffering a fractured rib in a pickup basketball game, and displayed a flair for making people squirm with his questionable social graces.

During a spring training media scrum, Greinke observed that he's no fan of "random people who come up and waste my time talking every day" by asking "stupid" questions. He topped that during a routine news conference at the National League Championship Series, when he said a lot of Milwaukee players don't like St. Louis pitcher Chris Carpenter because of his "phony attitude."

Greinke is alternately characterized as a free spirit, refreshingly candid, aloof, a baseball genius and socially awkward. For teammates, managers, coaches, media members and opponents who try to pigeonhole him, one-size-fits-all adjectives don't apply.

"He has baseball intelligence and a high baseball IQ," Melvin said. "He spends a lot of time with the video. He's educated to the new stat lines. He's a baseball junkie in a sense, and that's refreshing. I think it's healthy to see a player who wants to take control of his own situation -- with some guidance or counseling from an agent or whatever."

At age 28, with a 76-73 career record and three 200-innings seasons on his résumé, Greinke is positioned to hit the mother lode in free agency. Philadelphia's Cole Hamels is Plan A for teams in the market for an ace next winter, but Greinke became the best available alternative once Jered Weaver signed a five-year, $85 million extension with the Angels in August. Weaver pushed for the deal against the advice of his agent, Boras, because he's a Southern California boy who wanted to stay close to home.

Most people in the industry expect Greinke to retain an agent at some point, if only because big-ticket contract talks can be a full-time job. Indeed, since news of Greinke's free-bird status became known, agents have already been scrambling to track down his cell number and give him their pitch. He's about to get the same treatment as Jayson Werth, who changed agents during the 2010 season and received a flood of inquiries before settling on Boras.

"Ten agents have probably called Zack today," Melvin said. "He'll probably wish he never said anything."

Hands-on guys

By taking such an active role in his next contract, Greinke joins a select group of players to take the plunge. Gary Sheffield hammered out a three-year deal with George Steinbrenner several years ago, and numerous starting pitchers have played the role of lead dog in their negotiations. Is it because starting pitchers are smarter than everyday players, or because they have more time on their hands? That depends on whom you ask.

He is as intellectually curious, bright and understanding of the baseball metrics as any player I've ever come across. But the Zack Greinke that I know is equally smart and savvy enough that when the time is right, he'll have some counsel -- some specialist -- to protect and maximize his family's outcome.

-- John Courtright,
Greinke's former agent

Jamie Moyer has taken a hands-on approach in numerous contract talks, although his agent, Jim Bronner, was typically in the background dispensing advice. And Chuck Finley, Tim Belcher and Orel Hershiser were players who liked to be well-versed on the ins and outs of negotiations.

Curt Schilling took a well-publicized trip through the negotiation spin cycle in 2003. After Boston traded Casey Fossum, Brandon Lyon and two other players to Arizona for Schilling in November 2003, the Red Sox had a brief window to work out a contract extension with the pitcher. Executives Theo Epstein and Jed Hoyer traveled to Arizona for Thanksgiving dinner with the Schilling family, and the two sides worked out a two-year, $25.5 million extension with a third-year option.

Epstein later generated some laughs when he recalled how he saw a copy of the book "Negotiating For Dummies" on the desk in Schilling's den.

Schilling, a six-time All-Star and 216-game winner in the big leagues, began to play an active role in contract talks while pitching for Philadelphia in 1997. He eventually had a "major, major falling-out" with his representatives at the Beverly Hills Sports Council, and negotiated his own deals from 2001 until his retirement six years later.

Schilling highly recommends the experience.

"I think sports agents have grown mythical to the point where it's like politics," Schilling said. "Everybody is led to believe it's a far more complicated and difficult process than it is. There is no super-secret agenda. You know what every player in the big leagues makes, and the players' association can do an awful lot to assist players in contract negotiations. So it becomes a simple question of, 'Are you comfortable or not sitting in a room negotiating your salary?' A lot of guys aren't.

"I always figured I would just be paying somebody 5 percent of money I was already going to get. No one will ever look out for you more than you. If your agent represents players other than you, there will always be conflicts of interest. When an agent represents two free agents and one guy is a $150 million player and the other guy is a utility guy, the $150 million player is going to get the lion's share of the attention."

For what it's worth, Melvin already has experience dickering with players from his tenure as general manager in Texas. In December of 1998, Baltimore was engaged in parallel free-agent talks with Rafael Palmeiro and Albert Belle. Palmeiro, reportedly miffed that the O's planned to give Belle more money, reached out to management in Texas, where he had played previously in the early '90s. He met with Melvin at a hotel down the street from the Rangers' ballpark and they got down to business.

"I told him, 'If you want to tell me what you think you can [play for], put it on a piece of paper or a napkin and I'll take it back to ownership and see what we can do,'" Melvin said. Palmeiro scrawled the figure "$8.5 million" on a napkin, and Texas owner Tom Hicks later signed off on it. Palmeiro hit .324 with 47 homers in 1999, made the All-Star team and won a Silver Slugger award, and went on to play four more seasons in Texas. He was on his way to the Hall of Fame until that failed drug test in 2005.

Greinke, in contrast, is 28 years old and in the prime of his career. Someday soon, he'll have to start asking himself some difficult questions: As a man of few words, does he have the gift of gab necessary to sell himself to a prospective suitor? Will he be comfortable sitting down with a team owner if it comes to that? And in the end, will his next contract be about money, finding a comfortable landing spot, or a little of both?

"It doesn't surprise me to read some of the recent articles about Zack," said Courtright, Greinke's former agent. "He is as intellectually curious, bright and understanding of the baseball metrics as any player I've ever come across. But the Zack Greinke that I know is equally smart and savvy enough that when the time is right, he'll have some counsel -- some specialist -- to protect and maximize his family's outcome."

Baseball is baseball, and business is business, and Greinke has generated an intriguing debate by setting foot in both worlds. Over the next eight or 10 months, he'll prove whether or not he's capable of finishing what he starts.

Jerry Crasnick is a senior writer for ESPN.com. Click here to purchase a copy of his book, "License to Deal," published by Rodale. Crasnick can be reached via email.

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