Dave Winfield, Baseball Legend

If MLB first-ballot Hall-of-Famer Dave Winfield’s story tells us anything, it’s that you can’t judge a person by how things appear on the surface.

What we saw from the outside: a formidable 6’6”, 220 lb athlete who had just signed a 10-year, $23 million contract. (about $85 million in today’s money)

What was happening on the inside: self-doubt, anxiety, imposter syndrome, and the stress of a boss intentionally sabotaging him in the press and among his peers.

In 1980, Dave signed the biggest contract in baseball history with the New York Yankees, who had won two of the previous four World Series. From the minute he arrived in the Bronx, Dave became an object of derision to George Steinbrenner, the Yankees’ mercurial owner.

Seemingly for no reason, Steinbrenner insulted him in public, smeared him in private, and reneged on multiple contract obligations. He seemed to make the star player’s life miserable just because he could.

It seems counter-intuitive that a rich and famous athlete at the height of his physical and commercial prowess—someone who appeared to have everything—would describe those years as “the worst period of my life.”

And yet, that’s exactly the story Dave tells in his new memoir Touching All the Bases: A Story of Power, Purpose, and Surviving the Bronx and what he told me on this week’s episode of Reasonably Happy.

The 12-time All-Star, seven-time Gold Glove winner, and World Series champion lays out his side of the decade-long feud with Steinbrenner, and how he kept making All-Star teams despite the toxic work environment. We cover his getting drafted by three professional sports leagues, Hank Aaron’s warning about playing in Atlanta, signing the first 10-year contract in sports, finally getting his World Series ring in 1992, and, of course, the Canadian seagull that got him arrested.

Dave also shares what it was like to finally make peace with Steinbrenner before The Boss’s death in 2010.

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