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. Follow Dave: Instagram: @davewinfieldhof X: @DaveWinfieldHOF Follow Me: Instagram: @Paul-Ollinger X: @Paul-Ollinger Timestamps 00:00:00 Trailer 00:00:50 Intro 00:01:56 Pro baseball in 1973, when nobody played to get rich 00:04:40 His first bank went bankrupt, his second bank burned down 00:06:25 Growing up in Saint Paul 00:07:40 Drafted by the NFL without playing a down of college football 00:11:37 The yellow legal pad and studying the veterans 00:14:51 50 years of the Winfield Foundation 00:17:31 Free agency and the first 10-year contract in sports 00:20:05 Dinner with Ted Turner and Hank Aaron’s warning 00:23:13 Steinbrenner throws his lunch across the boardroom 00:26:22 “If you don’t like it, sue me” 00:29:58 How he kept performing through a toxic workplace 00:31:46 “The worst 15 years of my life” 00:33:19 Honorary doctorate in Syracuse, first pitch in the Bronx 00:35:09 The seagull incident in Toronto 00:37:39 Winning the 1992 World Series with the Blue Jays 00:39:25 Lightning round: toughest pitcher, best teammate, worst fans 00:42:53 Making peace with George Steinbrenner 00:46:22 Outro Get full access to Reasonably Happy at words.paulollinger.com/subscribe
