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AZ Tech Roundtable 2.0

AZ Tech Roundtable 2.0 with Matt Battaglia

The show where EntrepreneursTop Executives, Founders, and Investors come to share insights about the future of business


AZ TRT 2.0 looks at the new trends in business, & how classic industries are evolving

Common Topics Discussed: Startups, Founders, Funds & Venture Capital, Business, Entrepreneurship, Biotech, Blockchain / Crypto, Executive Comp, Investing, Stocks, Real Estate + Alternative Investments, and more… 


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Apr 11, 2024

Opening Day - Gambling & Charlie Hustle w/ Keith O’Brien + History of the World Series by Tyler Kepler NYT Baseball Writer

AZ TRT S05 EP14 (229) 4-7-2024 


What We Learned This Week

  • Gambling Scandal parallels of Pete Rose vs Dodger’s Shohei Othani
  • Charlie Hustle the icon - Rise & Fall
  • Business of Baseball - Drafting Players to Analytics & how the Game has evolved
  • History of the World Series - Did Babe Ruth call his shot?


Guest: Keith O’Brien 





Keith is the New York Times best-selling author of Paradise Falls, Fly Girls, and Outside Shot, a finalist for the PEN/ESPN Award for Literary Sports Writing, and an award-winning journalist. O’Brien has written for The New York Times, The Atlantic, The Washington Post, and Politico, and his stories have also appeared on National Public Radio and This American Life. He lives in New Hampshire.




About the Book

“CHARLIE HUSTLE: The Rise and Fall of Pete Rose, and the Last Glory Days of Baseball”


Pete Rose bounded out of the dugout like a hurricane spinning unfettered through the world. He slid head-first into bases in a mist of dust and fury. He sprinted out walks like a teenager. He was loud. Brash. Supremely confident. Entirely focused. He approached every game with ferocity and raw emotion—often like he was in the middle of a bar room brawl—and endeared himself to the fans because of it. He seemed to manufacture runs out of pure will power. He racked up mind-boggling stats and awards and streaks and wins and pennants and titles with seeming ease. When his team needed clutch hits, he provided them. When glory was 90 feet away, he reached for it. He bowled over catchers at home plate, shouted at pitchers to intimidate them, and ripped through middle infielders to break up the play. He would beat them all. One way or another. Pete Rose would never back down. Could never back down.


This spring, author Keith O’Brien and Pantheon Books will present the gritty and gripping new biography of the flawed legend—baseball’s tragic character—the man who could never return to the game he lived to play: “CHARLIE HUSTLE: The Rise and Fall of Pete Rose, and the Last Glory Days of Baseball” (Pantheon Books, March 26, 2024). It is a story unlike any other in baseball history. A story of virtuosity and success; addictions and secrets; recklessness and many missed opportunities for salvation. 


For over 25 years in Major League Baseball—from 1963 to 1989—Pete Rose was the sport’s unquestioned hero on the field. He was the heart of the Big Red Machine dynasty in Cincinnati. Rookie of the Year in 1963. MVP in 1973. He won three batting titles. Two gold gloves. Six National League pennants. Three World Series titles. He was named to 17 NL All-Star games at five different positions. He became the all-time hit king in the process, surpassing the legendary Ty Cobb. He was extraordinary while seemingly ordinary in equal measure, and the fans loved him for what they knew to be true. Pete Rose wasn't physically gifted or a particularly special athlete. He was like the rest of us. He was Charlie Hustle. The American Dream in red stirrup socks. Baseball personified. With bat in hand, Pete Rose was the hero, forever young, forever relevant, but a storm was coming.


Yes, Rose was both a miracle and a disaster. His opponents viewed him with both reverence and disdain. While some of them believed that his Charlie Hustle routine was a joke or that his aggressive antics were just plain dangerous, they respected his greatness and his longevity in the game. There was no doubt that he often came off as uneducated, unpolished, boorish, and rude, but most figured that he had earned the right to his “unique” perspective over the years. But then the rumors started to circulate that he was mingling with an unsavory crowd. Shady characters that included well-known bookies and gamblers. It wasn’t a secret that Rose had always been a gambler, but now there was growing evidence that he was betting on the sport that had made him a household name. With the 1919 Black Sox scandal looming as the cautionary tale still fresh in the game’s history, this growing storm threatened to destroy everything Rose had built. He could lose his livelihood and the game itself. It could strip away the mythology and dismantle the icon and reveal the very flawed human being he was off the field. So he did the only thing Pete Rose could do in the face of overwhelming evidence and his impending exile. 


He lied. And continued to lie for 15 long years.


CHARLIE HUSTLE also covers:

* His fraught relationship with his father—Pete Rose Sr.—the semi pro, Cincinnati sports legend

* How Rose overcame his lack of athleticism as a child with the intangibles that personified “Charlie Hustle”

* The terms of his first professional contract—enthusiastically signing for $7000 

* His early seasons of darkness in the lowest rungs of professional baseball

* The public relations bonanza when the local West High boy made the Cincinnati Reds’ Opening Day roster

* Rose’s long relationship with the city of Cincinnati

* His courtship and marriage to Karolyn Ann Engelhardt, which ended in divorce in 1979

* Rose's batting philosophies and the roots of his unusual crouching batting stance 

* Rose’s early entrees into gambling at spring training in Tampa—his infamous “triple headers”

* How Mickey Mantle and Whitey Ford came up with his “Charlie Hustle” nickname and how they had intended it to be an insult

* Rose's game-winning run in the 1970 All Star Game and how he and Ray Fosse were dinner companions the night before

* How "The Big Red Machine”—the nearly unbeatable Cincinnati Reds dynasty of the 1970s—took shape

* The details surrounding Rose’s affair with a girl half his age—a teenager—in the mid-1970s

* The early divide and rivalry between Pete Rose and teammate Johnny Bench 

* The revelation that Tony Perez was the true leader in the locker room for those Reds dynasty teams

* Rose’s rivalry with the Oakland A’s ace Jim “Catfish” Hunter during the 1972 World Series

* Rose's dust up with Bud Harrelson in the 1973 NLCS which left the Reds players fearful for their safety

* How Curt Flood’s fight for free agency affected Pete’s contract negotiations during the era

* Rose’s relentless pursuit of Joe DiMaggio’s 56-game hitting streak in the summer of 1978

* His brazen longtime affair with a woman named Terry Rubio, who would ultimately file a paternity suit against Rose

* Rose’s incomprehensible ability to play extremely well while going through all manners of personal turmoil

* Rose’s role as savior of the Philadelphia Phillies, a team that had never won a World Series, but soon would in 1980 after signing Rose as a free agent in 1979

* The details surrounding Rose’s single off of San Diego Padres’ pitcher Eric Show for hit number 4,192

* The rumors that Rose had been using a corked bat in his later years and may have even used them for his march to the hits record

* Background on the shady collection of bookies, railbirds, lackeys, dope dealers, and gofers who surrounded Rose in those later years

* The evidence that not only was Pete Rose a gambler, but a terrible gambler—he lost a lot 

* How and why a manager betting on his home team harms the game 

* The self-deprecating, chain-smoking academic from Yale University—A. Bartlett Giamatti—whose handling of the scandal as the Commissioner of Baseball was a master class in crisis management

* How an impending Sports Illustrated story about Pete Rose betting on baseball backed to baseball into a corner in how it dealt with the matter 

* How if Pete Rose had admitted to betting on baseball in an initial meeting with Peter Ueberroth, Bart Giamatti, and Fay Vincent, he most likely would have incurred a light punishment 

* The release of the Dowd Report, and the background of its special counsel, John Dowd

* The details surrounding Bart Giamatti's death in 1989

* The Baseball Hall of Fame’s response to Pete Rose’s candidacy

* How, in 2004, he published a book where he admitted to betting on baseball and on the Cincinnati Reds

* How reinstatement eluded him—in 2004, 2015, 2020, and 2022—and, if anything, his situation grew worse

* Theories why Rose hasn't I been forgiven to date

* Baseball’s ever-evolving relationship with sports gambling and what that means for Pete Rose and for the future of the sport

* The six simple words that might have changed everything: “I'm sorry I bet on baseball.”


New York Times bestselling author Keith O'Brien grew up in Cincinnati when Pete Rose was at the peak of his fame and witnessed his shocking downfall first-hand. More than three decades later, it’s hard to appreciate how much the controversy became such a part of the American conversation. The mythology surrounding Pete Rose was so fixed and strong that the disgust, frustration, pity, and confusion that followed his banishment stirred endless debates about the man, the allegations he faced, and, in turn, about the game of baseball itself as arbiter. Rose quickly became a fault line in the collective American conscience, and it clearly marked the end of the age of innocence in sports. O’Brien documents all of this like never before in CHARLIE HUSTLE, with unprecedented reporting and access. He met with Rose in person and they spoke on the record for 27 hours, before Rose stopped calling back, before he shut down. O’Brien is the only biographer that Rose has ever spoken to when he didn't have any editorial control. 


Beyond those conversations, O’Brien delved into thousands of pages of previously unutilized federal court documents, newly released FBI files, raw TV footage, decades of newspaper articles, Major League Baseball's voluminous 1989 investigation into Rose’s misdeeds; and nearly 150 hours of interviews with Rose's friends, enemies, former teammates, family members, two former Commissioners of baseball, three people who placed his bets, four different investigators who dug up his secrets, and the special counsel who led the charge, John Dowd.


Pete Rose loved baseball and wanted to play forever. Keep hitting forever. Never grow old. Never stop swinging. Never go home. But the same qualities that made him a successful baseball player—and one of the greatest hitters of all time—ensured his banishment. He couldn’t be vulnerable. Couldn’t beg for forgiveness. Or even apologize until it was far too late. Doomed by his own ignorance and hubris, Pete Rose was going down.









Tyler is the author of the New York Times bestseller K: A History of Baseball in Ten Pitches. He has covered every World Series game of the last two decades for The New York Times. He started his career as a teenager, interviewing players for a homemade magazine in the early 1990s. He attended Vanderbilt University on the Grantland Rice/Fred Russell sportswriting scholarship, then covered the Angels for the Riverside (Calif.) Press-Enterprise and the Mariners for the Seattle Post-Intelligencer. He joined The New York Times in 2000, covering the Mets for two seasons, the Yankees for eight, and serving as the national baseball writer since 2010. 

From the New York Times bestselling author of K: A History of Baseball in Ten Pitches, a highly entertaining, revelatory history of the World Series, filled with gripping behind-the-scenes stories from 117 years of the Fall Classic. 

The World Series is the most enduring showcase in American team sports. It’s the place where legends are made, where celebration and devastation can hinge on a fly ball off a foul pole or a grounder beneath a first baseman’s glove. And there’s no one better to bring this rich history to life than New York Times national baseball columnist Tyler Kepner, whose bestselling book about pitching, K, was lauded as “Michelangelo explaining the brush strokes on the Sistine Chapel” by Newsday. In seven scintillating chapters, Kepner delivers an indelible portrait of baseball’s signature event. He digs deep for essential tales dating back to the beginning in 1903, adding insights from Hall of Famers like Reggie Jackson, Mike Schmidt, Jim Palmer, Dennis Eckersley and many others who have thrived – and failed – when it mattered most. 

Why do some players, like Madison Bumgarner, Derek Jeter and David Ortiz, crave the pressure? How do players handle a dream that comes up short? What’s it like to manage in the World Series, and what are the secrets of building a champion? Kepner celebrates unexpected heroes like Bill Wambsganss, who pulled off an unassisted triple play in 1920, probes the mysteries behind magic moments (Did Babe Ruth call his shot in 1932? How could Eckersley walk Mike Davis to get to Kirk Gibson in 1988?) and busts some long-time myths (the 1919 Reds were much better than the Black Sox, anyway). 

The result is a vivid portrait of baseball at its finest and most intense, filled with humor, lore, analysis and fascinating stories. THE GRANDEST STAGE is the ultimate history of the World Series, the perfect gift for all the fans who feel their hearts pounding in the bottom of the ninth inning of Game Seven.








Tyler Kepner wrote the grander stage the history of the World Series about baseballs October classic. Is the New York Times national baseball radar and has a background in being a bit writer for teams.

He’s originally from Philly. He was an intern at the Boston Globe and then the Washington post. Got a job out of college covering the Angels. Then got a job covering the Seattle Mariners for a newspaper in Seattle. In 2000 he got a job at the New York Times covering the mats for two years. Then he was covering the Yankees for eight years. 2010 he became the New York Times national baseball writer.

Writing the book on the history of the World Series was a lifelong goal. He had written a previous book about pitching called K. The book was a three-year project to write. Tyler has covered 24 World Series dating back to 1998 as well as gone to two as a fan, 1983 series with the Phillies as a kid and then 1993.

Tyler always follows good stories for his baseball writing. The 2022 baseball playoffs started in St. Louis to see about Albert polos last games. Then moved on to cover the New York Yankees. And then he’s going to see the Seattle Mariners as they are in the playoffs for the first time in years.

TV ratings for baseball have been decent. Still gets very good ratings in local markets. Baseball like other sports is still live programming and and they jam of TV. Sports creates appointment setting type TV.

When you cover baseball as a rider, you will go to the ball park about 2 PM for a 7 PM game. He would mall around the stadium and clubhouse talk with players the manager may be the GM.

Most days he’s writing, with a deadline by the night time to be able to post by the next day. Player access in baseball is pretty open, it’s an every day business and they give the media plenty of room to work.

Tyler missed game seven of the 2001 World Series in Arizona versus the Yankees because of a family commitment.

Baseball business as no hard salary cap, just some luxury taxes. It is expensive to build a team as you need free agents but also good scouting and player development. There’s a lot of have and have Nots. Many of the smaller teams like the Oakland A’s I’ve had player stolen by big teams like the Yankees or the Red Sox, almost acting like farm systems for the bigger teams.

Baseball has changed over the years with the introduction of analytics and stats that now dominate the game. The teams that use at the best and can communicate the info to the players usually win.

A great example of this is the GM of the Dodgers Andrew Friedman, who previously had been the GM of the Tampa Bay rays. Dodgers are well run team have a little bit of a small team mentality where they draft and develop players well, but also of the big resources and money to get the free agents.

Teams have to convince the players how data will help their game. It isn’t that hard since the new generation has been raised on their cell phones and data. The idea being a singing how are you can swing better, or what is a better pitch for a pitcher to use so that players can play well.

Older guys in baseball lament the analytics and how it’s changed the game.

Amateur players understand how they have to do well on the metrics, and how hard they hit the ball, and swing playing in velocity. The older scouts and baseball people dislike the fact that it’s not about moving the runner over in contact anymore.

The game has evolved and the analytics and the data shows you what you need to do to win.

Sports, including baseball is good for TV because it has live programming and people still watch live programming. Baseball games still may take longer but they still get OK national ratings and very good local ratings.

Baseball is working on a little changes for more balls in the way and excitement. There is a lot of home runs and strikeouts right now.

Baseball making some rule changes to affect us like regulating the shift and how the defense fields, changes to the baseball and maybe bigger bases to encourage base running aggressiveness in more stolen bases as examples.

Billy Beane of Moneyball and the Oakland A’s popularized baseball analytics and data. Been had a classic line I pay you to get on base, not to get caught stealing. No risky place.

Tyler wanted to write World Series stories that people don’t know. An example is what happened in the next game after Don Larsen throws a perfect game for the Dodgers. What happened to setup Kirk Gibson home run in 1988 vs As

Tyler loves the art of pitching and the slider and the knuckleball. He had written a previous book K the history of baseball and 10 pitches.

Did Babe Ruth call his shot? That is the legend, but it is not true. Babe Ruth told the Cubs he was going to do some thing, but did not point at offense. Back then the cubs pitchers would’ve thrown at Babe Ruth if he was showboating like that.





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AZ Tech Roundtable 2.0 with Matt Battaglia

The show where EntrepreneursTop Executives, Founders, and Investors come to share insights about the future of business

AZ TRT 2.0 looks at the new trends in business, & how classic industries are evolving

Common Topics Discussed: Startups, Founders, Funds & Venture Capital, Business, Entrepreneurship, Biotech, Blockchain / Crypto, Executive Comp, Investing, Stocks, Real Estate + Alternative Investments, and more… 


AZ TRT Podcast Home Page:

‘Best Of’ AZ TRT Podcast: Click Here

Podcast on Google: Click Here

Podcast on Spotify: Click Here                   

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