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Episode Summary

As Major League Baseball gets closer to starting up this season, we visit with the CEO of the Toronto Blue Jays, Mark Shapiro, and his father, the “accidental agent” and sports insider Ron Shapiro. These two baseball lifers tackle the social and economic architecture of the sport, share personal stories of life in and around the game, and discuss the challenges people in baseball are facing to get back on the playing field. And one more thing - listening to the interplay between father and son will stick with you long after this episode of The Sydcast is done.

Syd Finkelstein

Syd Finkelstein is the Steven Roth Professor of Management at the Tuck School of Business at Dartmouth College. He holds a Masters degree from the London School of Economics and a Ph.D. from Columbia University. Professor Finkelstein has published 25 books and 90 articles, including the bestsellers Why Smart Executives Fail and Superbosses: How Exceptional Leaders Master the Flow of Talent, whichLinkedIn Chairman Reid Hoffman calls the “leadership guide for the Networked Age.” He is also a Fellow of the Academy of Management, a consultant and speaker to leading companies around the world, and a top 25 on the global Thinkers 50 list of top management gurus. Professor Finkelstein’s research and consulting work often relies on in-depth and personal interviews with hundreds of people, an experience that led him to create and host his own podcast, The Sydcast, to uncover and share the stories of all sorts of fascinating people in business, sports, entertainment, politics, academia, and everyday life. 

Mark Shapiro

Over a career that spans 28 seasons, Mark Shapiro is one of the rare executives in Major League Baseball that has had the opportunity to lead and impact baseball, business, and league operations. Widely considered one of MLB’s top executives, he was appointed as President & CEO of the Toronto Blue Jays in November 2015, following 24 seasons within the Cleveland Indians organization. 

Mark began his career in baseball in 1992 when he joined the Cleveland Indians as an assistant in Baseball Operations. He quickly moved up the ranks and spent five seasons (1994 to 1998) overseeing all aspects of the Indians’ player development system as Director of Minor League Operations, before becoming Vice President of Baseball Operations & Assistant General Manager from 1999 to 2001. 

Following both the 2005 and 2007 seasons, Shapiro was named the Sporting News “Executive of the Year,” at the time the only active GM in MLB to win the award twice. In 2005 he was also named “Executive of the Year” by Baseball America, and after the 2006 season, the Indians organization was named “Organization of the Year” by TOPPS for the first time. In 2007, Mark was named to the elite “40 under 40” by Sports Business Journal, as well as being listed on Baseball America’s “10 to Watch” list. 

Ronald M. Shapiro

Expert Negotiator, Sports Agent, Attorney, Educator, New York Times Bestselling Author, and Civic Leader, Ron Shapiro attended Haverford College and graduated Cum Laude from Harvard Law School in 1967. USA TODAY called Ron Shapiro “one of baseball’s most respected agent-attorneys,” and the Sporting News named him one of the “100 most powerful people in sports.” His impressive list of clients included more Hall of Famers than any other agent, including Cal Ripken, Jr., Jim Palmer, Brooks Robinson, Kirby Puckett, Eddie Murray, and 2009 AL MVP, Joe Mauer, who have collectively benefited from the more than one billion dollars in contracts that Mr. Shapiro has negotiated on their behalf. 

In addition, Mr. Shapiro is the Special Advisor to the owner of the NFL Baltimore Ravens, and has played similar roles for the General managers of the NBA San Antonio Spurs, Oklahoma City Thunder and the Brooklyn Nets. He has written multiple bestselling books, lectured at numerous top universities, has appeared as a negotiations expert on ABC’s Good Morning America, ESPN’s Mike and Mike in the Morning, and many other media outlets. 

Committed to public and civic matters, Mr. Shapiro has chaired over 25 boards of charitable and community organizations. Mr. Shapiro has received numerous special honors and recognitions, including recipient of The American Red Cross Lifetime Achievement Award in 2013. Mr. Shapiro’s dispute resolution techniques have settled a major symphony orchestra strike, facilitated solutions to human relations problems, and resolved disputes in governmental, corporate, and major biotechnology challenges. 

Mr. Shapiro has negotiated on behalf of, or served as deal coach to, Fortune 500 companies, government agencies, sports teams, and entertainment and news personalities. Ron Shapiro is frequently cited by parties representing each side in a negotiation as the ultimate Win-Win negotiator.

Insights from this episode:

• Details on how and why Ron Shapiro went from being a corporate securities lawyer to a sports agent in the mid 1970’s and how he helped shape the role of sports agent as a player’s advocate.
• How growing up in the world of baseball shaped Mark Shapiro’s life and career.
• Differences between the financial structure of Major League Baseball versus other major league sports institutions.
• Strategies Major League Baseball is employing to continue to move forward not just during the COVID-19 but also maintain relevance in the future. 
• Details on the biggest threat to Major League Baseball throughout its history and how that continues to impact the sport today.

Quotes from the show:

• On being an agent in the 1970’s: “Everything you did was groundbreaking because every new contract had a new implication.” – Ron Shapiro 
• “That was a different time of agents. Agents now are about recruiting and retention; my father modeled agents as advocates.” – Mark Shapiro
• How the Shapiro’s approach negotiations: “In the corporate world, in the baseball world, in any world you want to do good deals and you want the other side to feel that they’ve got a good deal, but you want to have a working relationship to build on that after the fact.” – Ron Shapiro
• On the effects of COVID-19: “Our country is becoming more and more divided economically and from a survival point of view.” – Ron Shapiro
• On our future with COVID-19: “People make predictions, but that’s all they are is predictions. We don’t know where we’re going with this.” – Ron Shapiro
• On leading people during COVID-19: “I’ve tried to walk that line between the importance of being transparent and being open but still being hopeful and optimistic.” – Mark Shapiro
• “I’ve always thought, as a citizen of the world, you have a responsibility to be alert to what’s going on and to try to help other people.” – Syd Finkelstein
• “When people view Major League Baseball they often don’t understand that the major league team is just the tip of the spear and that there’s an entire organization underneath.” – Mark Shapiro
• “We’re not dealing with challenges that are unique to MLB [Major League Baseball] we’re dealing with global challenges that people are facing at some scale and at some level throughout the entire world.” – Mark Shapiro
• On dealing with the stress of COVID-19: “That’s a principle that I think always applies; try to focus on things you can control and don’t let all those other things make you crazy.” – Syd Finkelstein
• “We will not shut down. We will keep playing.” – Mark Shapiro

Stay Connected:

Syd Finkelstein

Website: http://thesydcast.com

LinkedIn: Sydney Finkelstein

Twitter: @sydfinkelstein

Facebook: The Sydcast

Instagram: The Sydcast

Mark Shapiro

Twitter: @MarkShapiro

Instagram: @bluejays

Ronald M. Shapiro

Twitter:@ronaldmshapiro

Website: shapirosher.com

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This episode was produced and managed by Podcast Laundry (www.podcastlaundry.com)