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Contract Negotiation MLB Players Sports Agents

Scott Boras: The Devil Wears Jeans?

When Scott Boras isn’t busy eating your children, he is actually baking cookies for his employees.

Our boy, Jason Wulterkens, not only knows his fair share about golf, but is knowledgable about the entire industry. He has decided to share a second contribution to this site, and will officially become a contributor after this post (check out the full list of contributors @ the About page). Enjoy his final post as a subscriber:

In its April, 2001 edition, Esquire writer Scott Raab called Scott Boras the Most Hated Man in Baseball, the heartless bastard hell-bent on destroying our National Pastime, the keen-eyed pimp of ball-hogging, bat-whipping, splitter-hurling youth. [Jackpot!]

But nearly six years later, the April 2007 issue paints the oft-feared super-agent in a somewhat gentler light. Writer Chris Jones piece is in fact one of the most in-depth, unadulterated and behind-the-scenes looks at sports contract negotiation that I have read, and is a must-read for any would-be agent, as well as anyone else in the sports industry alike. The article even takes a peek inside of Boras Corporation, where Boras routinely shows up to work in blue jeans, and bleary-eyed employees are treated to fresh baked cookies midday. Sounds lovely.

Esquire’s new article centers around the life, and newly invigorated mindset of, San Francisco Giant’s off-season splurge, pitcher Barry Zito. However, it devotes as much space, if not more, to Boras, Zito’s agent and close friend. Detractors and Boras-loyalists alike have always agreed on one thing: Boras, and his legion of employees, player-scouts, statisticians and lawyers that comprise the insides of the sleek and newly finished Newport Beach, CA based Boras Corporation, are some of the most well-prepared negotiators and client/player advocates in baseball. As the article points out, Boras has at his disposal a state of the art computer system that has tracked every single pitch of every single game since 1971. Armed with more data than most General Managers would dare dream of, Boras thus typically enters any arbitration hearing or contract negotiation ready for war, his team of assistants brandishing briefcases and folders of information. And more often than not, he wins the battle. If there was ever an example of the success of over-preparation when planning for a negotiation, Team Boras is it.

That said, the article also shines a light on how much Boras personally cares for his clients’ well-being. During the Zito negotiations, for example, the reader gets the impression that, although Zito’s 7-year, $126 million deal was the largest deal ever for a pitcher, Boras’ main priority throughout the negotiation process wasn’t so much about securing a landmark deal per se. Rather, Boras seemed consumed with helping Zito to decide for himself where he would be most comfortable. And when it became clear to both men that Zito would not have been a good match with the New York Mets, despite their aggressive solicitations, Boras made no qualms about scratching them off the list of contenders.

Between the lines, Zito seemed more appreciative of the personal-side of Boras, than his number-crunching, heartless, no-holds barred agent side. Boras is Zito’s agent. But moreover, he is Zito’s personal friend. Though the two men had a falling out years ago, Zito eventually returned to Boras. One can’t help but think that his reason for doing so went beyond sheer finance. Now, Zito and Boras finally seem to see eye-to-eye on a personal level. In this sense, representing one’s client is much more than mere zealous advocacy and cutthroat carte-blanche negotiation. It means being there for them as a friend.

By Darren Heitner

Darren Adam Heitner, Esq., is a preeminent sports attorney and the founder of Heitner Legal, P.L.L.C., a Fort Lauderdale-based law firm specializing in sports law, contract negotiations, intellectual property, and arbitration. He earned his Juris Doctor from the University of Florida Levin College of Law in 2010 and a Bachelor of Arts in Political Science, magna cum laude, from the University of Florida in 2007, where he was named Valedictorian of the College of Liberal Arts and Sciences. Admitted to practice in the state bars of Florida, New York, and the District of Columbia, as well as multiple federal courts, Darren also serves as a certified arbitrator with the American Arbitration Association.

As an adjunct professor, Darren imparts his expertise through teaching Sports Law at the University of Florida Levin College of Law and Name, Image, and Likeness (NIL) at the University of Miami School of Law in the Entertainment, Arts, and Sports Law LL.M. program. His scholarly contributions include authoring several books published by the American Bar Association, such as How to Play the Game: What Every Sports Attorney Needs to Know, and numerous articles in prominent publications like Forbes, Inc. Magazine, and Above the Law. His thought leadership in NIL has earned him recognition as one of the foremost experts by The Wall Street Journal, USA TODAY, and On3, and he has been lauded as a “power player in NIL deals” by Action Network and a “top sports trademark attorney” by Sportico.

Darren’s passion for sports law led him to establish Sports Agent Blog on December 31, 2005, initially titled “I Want To Be A Sports Agent.” The platform, created as a New Year’s resolution, has grown into a cornerstone of the sports agency community, offering in-depth analysis of industry trends, legal disputes, and agent-player dynamics. His commitment to the field is further evidenced by his representation of numerous athletes and sports agents, as well as his prior role as an Adjunct Professor at Indiana University Bloomington, where he developed and taught a course on Sport Agency Management from 2011 to 2014.

Darren’s contributions have been recognized with prestigious honors, including the University of Florida’s 40 Under 40 Award, the University of Florida Levin College of Law’s Outstanding Young Alumnus Award, and designation as the best lawyer in Fort Lauderdale by Fort Lauderdale Magazine. He remains an active voice in the sports law community, sharing insights through his weekly NIL newsletter and his X posts, engaging a broad audience on legal developments in sports.