The 2024 World Series between the New York Yankees and Los Angeles Dodgers will commence on Friday (Oct. 25 at 8:08 p.m. ET on FOX) from Hollywood, setting off one of the most anticipated Fall Classics to date. Representing the United States’ two premier media markets, both sides are riddled with star power.
Undeniably, MLB’s best two hitters are here via the Dodgers’ Shohei Ohtani and Yankees’ Aaron Judge. Like Playboy, these blue blood baseball franchises are no strangers to dealing with the world’s top talent.
The Yankees and Dodgers are as high-profile as it gets. Naturally, many of their former players have spoken with Playboy over the years, sitting for an interview or 20Q.
Prior to meeting in the World Series for a record 13th time, here is a list of Yankees or Dodgers that have given a Playboy Interview throughout the publication’s history:
Derek Jeter – Yankees
A man informally considered New York’s top bachelor of the 2000s, former shortstop Derek Jeter is the most recent Yankee to sit down for a Playboy Interview. Back in June 2004, Jeter discussed with Playboy what it’s like to navigate life in the city, winning four championships, playing alongside Alex Rodriguez and more. Of course, the then-Yankee captain would go on to add one more World Series title in 2009 before retiring five years later. Jeter was enshrined in the MLB Hall of Fame in 2020.
Read Derek Jeter’s Playboy Interview here.
Mike Piazza – Dodgers
Slugging catcher Mike Piazza chatted with Playboy back in June 2003 when he was a member of the New York Mets. Still, Piazza spent the first six-plus seasons of his MLB tenure with the Dodgers. Under the guidance of family friend and Los Angeles manager Tommy Lasorda, the burley backstop became one of the best batters in baseball. Unfortunately, Piazza lost the only World Series he ever played in, falling short with the Mets against the Yankees in 2000. He was inducted into Cooperstown in 2016.
Read Mike Piazza’s Playboy Interview here.
George Steinbrenner – Yankees
There have been countless owners across professional sports but none quite like George Steinbrenner. “The Boss” was exactly that of the New York Yankees for more than 30 years. Steinbrenner was once forced out of MLB only to be let back in (which is another story for another time). In May of 1991, Steinbrenner talked with Playboy about various nuances of the job, winning titles, being banned from management of the Yankees, performing on Saturday Night Live and more.
Read George Steinbrenner’s Playboy Interview here.
Rickey Henderson – both, technically
Rickey Henderson is one of the most gifted baseball players to ever take the diamond. He holds MLB records for the most runs scored (2,295) and is the only player to eclipse 1,000 stolen bases (1,406). Although he is mostly known for his stints with the Oakland Athletics, the speedy outfielder also suited up for the Yankees and Dodgers. He was with the Yanks throughout the late 1980s. Henderson played only 30 contests for the Dodgers in 2003, which were his final games in baseball. He won two World Series titles in his career (with the A’s and Toronto Blue Jays) and was inducted into MLB’s Hall of Fame in 2009. Henderson interviewed with Playboy in September 1990—just 15 months after the Yankees traded him back to Oakland.
Read Rickey Henderson’s Playboy Interview here.
Roger Craig – Dodgers
Baseball-lifer Roger Craig spoke to Playboy in 1988 while serving as the San Francisco Giants manager. However, Craig has experience on both sides of the rivalry, as he pitched for the Dodgers throughout his first seven MLB seasons. Notably, Craig was a member of the Dodgers when the franchise relocated to Southern California in 1958. He is one of the few men to play multiple years for the “Boys in Blue” in both Los Angeles and Brooklyn. Craig won four World Series in his lifetime MLB tenure, but only two of those came as a player—both with the Dodgers (1955, 1959).
Read Roger Craig’s Playboy Interview here.
Wade Boggs – Yankees
Wade Boggs — owner of 3,010 career hits at the MLB level — was the vintage sweet-swinging lefty of the 1980s. Boggs is most famous for his days with the Boston Red Sox where he spent 11 campaigns smashing the baseball. When the corner infielder sat down with Playboy in July 1987, he was en route to earning his third of four consecutive A.L. batting titles for the Red Sox. Still, Boggs won his lone World Series ring in 1996 with the rival Yankees just four seasons after departing Boston. He earned Cooperstown’s immortality in 2005.
Read Wade Boggs’ Playboy Interview here.
Steve Garvey – Dodgers
Prior to his run for U.S. Senate in California, Steve Garvey was once a smooth-fielding first baseman for the Dodgers. He won four Gold Gloves for Los Angeles throughout the mid-1970s and was named N.L. MVP in 1974. Playboy chatted with Garvey in June of 1981, which was just four months prior to him and the Dodgers defeating New York in the 1981 World Series. Ironically, that was the most recent year in which these sides met head-to-head for the title.
Read Steve Garvey’s Playboy Interview here.
Halloween is on the horizon—read the 5 Coolest Items Under $50 at Spirit Halloween.
