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Baseball Winter League Agreement Puts New Restrictions On Players Seeking To Play In The Caribbean

Boston Red Sox designated hitter David Ortiz (34) hits a grand slam during the eighth inning in game two of the American League Championship Series baseball game against the Detroit Tigers at Fenway Park. Mandatory Credit: Greg M. Cooper-USA TODAY Sports
Boston Red Sox designated hitter David Ortiz is fond of representing his country, the Dominican Republic. Photo Credit: Greg M. Cooper-USA TODAY Sports

Winter Ball is a great opportunity for baseball players to stay sharp during the offseason by playing for teams in the Dominican Republic, Venezuela, Puerto Rico and Mexico.  When I was a baseball agent, I placed multiple clients in Puerto Rico’s Winter League, and each of those players cherished the opportunity to build on their existing skill-set while earning some additional money in the offseason.

Winter League baseball is not simply relegated to those players making their way up their respective farm systems.  Oftentimes Major League players wish to get involved whether it be to continue to develop their form and/or to play for their countries of origination.  For instance, David Ortiz of the Boston Red Sox has played many years in the Dominican Republic’s Winter League.

So when it seemed as though baseball players’ on their teams’ 40-man roster may be prohibited from participating in the various Winter Leagues, players and agents became quite upset.  However, that potential issue has now been resolved.  Major League Baseball and the MLBPA have come to terms on a new deal that will allow said players to participate, with the stipulation that certain players who were worked very hard during the season will be prevented from playing in the Winter Leagues.

Double-A starting pitchers on their clubs’ 40-man rosters will be held out from Winter League play if they threw 140+ innings the prior season.  Double-A relievers must stay under 45 games pitched in order to be granted clearance.  If a pitcher stayed in his role (as either starter or reliever) and increased his workload by at least 25% over the prior year, then he will also be ruled ineligible for Winter Ball participation.

Alternatively, restrictions on position players have been loosened.  The old threshold was 502 plate appearances or more and the player was withheld from Winter League competition.  That threshold has been increased to 552, making it possible that more position players will be eligible to play.

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.