The Boss, The Captain, and The Dark Knight: Stories from Baseball Insider Ken Davidoff
Plus lessons from his new book, 101 Lessons from the Dugout.
Ken Davidoff will always remember where he was when his phone rang on February 14th, 2003.
In those days, Yankees owner George Steinbrenner was known for making headlines. Wait, that is an understatement. Steinbrenner was known for making big, bold, 72-point back-page headlines that sold tabloid newspapers like Newsday, Ken’s employer. And reporters and columnists got those headlines by chasing Steinbrenner down the hallway in the Yankees Spring Training complex, shouting questions in an effort to get The Boss to stop and bluster.
As Davidoff was running down the hallway to catch Steinbrenner, his phone rang. It was his wife, Sarah, calling with the happy news that she was pregnant with their first child. On Valentine’s Day, no less.
Welcome to the life of a baseball writer.
Ken was wise enough not to tell Sarah, ‘Hey, let me call you back,’ and thus they are still married. He also outlasted the napping George Costanza, the enigmatic A-Rod, and the Captain, Derek Jeter, while covering the Yankees (and later Mets).
Covering the Yankees had been Ken’s childhood dream since he was seven. He had climbed the ladder from small-town paper to suburban paper to urban paper, and from covering high school sports to the New York Yankees. In 2004-05, he became the baseball columnist for Newsday, adding the Mets and the rest of MLB to his coverage portfolio. In 2012, he moved over to The New York Post. And, oh, the people he met. Those baseball fans know by one word, like Reggie and Bernie.
Above all, he never got outworked. See Steinbrenner, George.
That takes a toll on a man. As does traveling 150 days a year and having little to no work-life balance. But childhood dreams die hard, so he kept going for a while. By 2022, though, he had lost his passion for the grind and was severely burned out. With Sarah’s encouragement, he gave his notice. He had no idea what he would do instead. He just knew it was not this anymore.
“I made the decision to get off the hamster wheel, if you will,” Davidoff said. “I’ve been calling it retirement, mostly because that word seems to annoy people. I was burned out professionally. I couldn’t write another column on why the Yankees had lost five of seven. I couldn’t chase down another trade rumor.”
As is often the case, when you close one door, another one opens. Or in Davidoff’s case, two.
The first was to be an adjunct professor at Endicott College in Beverly, MA, teaching journalism to undergraduates. Three days after Davidoff announced his retirement from sports writing on Twitter, Endicott College President Steven DiSalvo reached out to Davidoff. Their twenty-year relationship had sprouted from DiSalvo’s time as executive director of Joe Torre’s Safe At Home Foundation. A plan emerged for Davidoff to get involved at Endicott, including teaching. He has taught classes since the Spring of 2023, such as Sports Journalism, Feature Writing, Multimedia Journalism, and Contemporary Issues in Journalism.
“He’s been around a long time and certainly had the experience and the leadership lessons to share,” DiSalvo said. “The other part is you have to be humble in telling the stories and not braggadocios. And Ken has this quality of conveying information to the student without making it seem like he is just talking about himself. And I thought that was the type of person who could really connect with undergraduates.”
For Davidoff, it was a chance to pay it forward. That has included both teaching and helping his students make connections in sports management and sports journalism.
“I know how many people helped me along the way, and I get great joy from helping younger people achieve their dreams,” Davidoff shared in an article on the Endicott website.
“If you asked me to name anybody in the sports journalism business who would be the perfect instructor to aspiring students, it would be Kenny,” said the New York Post’s Managing Editor, Sports, Mark Hale. “The combination of intelligence, character, wisdom, and talent, and the universal respect he has earned make him the ideal mentor.”
Another chance to pay it forward had emerged in January 2022 between the time Davidoff decided to give his notice and when he shared it with his boss.
“This book came to me not in a vision but literally came to me from my co-author, Dr. Harley Rotbart,” Davidoff explained. “101 Lessons from the Dugout is his baby. It’s about the life lessons that can be learned from baseball and softball. It is targeted for a young audience, ages 12 and up, but I think it can be enjoyed by folks of all ages.”
The timing was perfect for Davidoff.
“So along comes this book, which enables me to leverage all my knowledge and insight and experience writing about the game itself, but also a book that’s sweet and positive. My job was to be a hard-hitting journalist, and I loved that job for a very long time, but it’s exhausting. It was the perfect antidote for me because I was so tired of the grind of Major League Baseball. To do something like this was very energizing.”
Rotbart and Davidoff worked together like Andy Pettitte and Jorge Posada. Rotbart was the pitcher who developed the 101 lessons, drawing on his experience as a pediatrician, parenting expert, and youth baseball coach. Davidoff, a former Little League coach, then caught and framed them by adding context and polish from his time in the game.
“I thought I would just help with getting someone to write the forward after my agent connected us,” Davidoff shared. “Harley took a leap of faith and said, ‘Ken, I’d like you to be my co-author and really roll up your sleeves.’”
“His connections were fantastic,” Rotbart shared. “But the most important thing he brought was a skill set and knowledge of the game that enabled us to translate baseball into real-life lessons. We both love the game, and we each brought different aspects.”
Amazingly, Rotbart and Davidoff have never met in person despite having conducted dozens of Zoom calls and joint interviews. Despite this, Rotbart says he feels like he has known Davidoff his whole life. Rotbart lives in Denver and suggested perhaps they meet this summer for a game at Wrigley.
A common misconception is that Davidoff directly shared lessons from his time covering the game. Instead, he more subtly infused those lessons, like one he witnessed from Luis Castillo, a longtime Marlins and Mets second baseman (who also played a couple seasons for the Twins for fellow Immaculate Gridders out there).
“It is 2009, and a Subway Series game between the Yankees and Mets. K-Rod (Francisco Rodriguez) is pitching to A-Rod (Alex Rodriguez). Rodriguez hits a two-out pop-up. Game over. Except the ball hits Castillo’s glove and falls out. And because it is two outs, everybody is running, and the Yankees win. It was one of the most startling ends to a game I have ever witnessed.
“And the next day, Saturday, I remember sitting in the Mets clubhouse and wondering what Castillo would look like when he walked in. Sure enough, he walks in, smiling, joking, talking to the media, and he has a heck of a game, and the Mets win. What a lesson in that for kids to grow from your mistakes and stay in the moment and show up the next day ready to get back at it.”
Davidoff rattles off the chapter and verse of this lesson like a pastor quoting scripture. The passage below is from Chapter 57, Errors.
“People are not perfect, and they make mistakes. One way to measure yourself as a player — in baseball and softball, and in life — is what you do and how you do it after an error. Do you hang your head, kick the dirt, throw your helmet, and lose your focus? Or, do you pound your glove with your fist and move on to the next play?” - Chapter 57 Errors from 101 Lessons from the Dugout: What Baseball and Softball Can Teach Us About The Game of Life
One of the most critical chapters for Davidoff is Chapter 2: The Starting Lineup.
“In this scenario, you go to the field, and you are not in the starting lineup,” he shares from the book. “How are you going to deal with that? Are you going to put your head down and drag all day, or are you going to say okay it is my mission to prove the coach wrong and be the best substitute I can be.”
One of my favorites was Chapter 4, Batting Order. It builds on Chapter Two.
“The first limbo bar is, did you make the starting lineup?” Davidoff said. “And the second limbo bar is then where you are hitting. And we know that is a big thing even for big leaguers. There was a playoff game in which Joe Torre hit A-Rod eighth. And I think their relationship never really recovered from that. So it matters at the highest level, and for sure at the lowest levels.”
At this point, Davidoff begins sharing from the bible book again.
“You’re only a number nine hitter if you believe the label and start to think like a number nine hitter. As you play through the innings of your life, you determine your own success at the plate, regardless of how you are labeled by others….if someone brands you a number nine hitter in any part of your life, don’t fall for it. Ignore the labels. Play every game the best you can, no matter what the expectations are of those around you.”- 101 Lessons from the Dugout: What Baseball and Softball Can Teach Us About The Game of Life
Davidoff then cites the example of Derek Jeter, who began his career as the number nine hitter in the Yankees lineup when he was promoted to the Major Leagues in 1995. Jeter played in 15 games that year, batting ninth in twelve of them and eighth in the three others.
Another lesson is Chapter 70, Go With Your Strengths.
“In life, when you really need a strike, you should go with your strengths and whatever has given you the best results in the past. Stick with what works, nothing fancy or mysterious.” - 101 Lessons from the Dugout: What Baseball and Softball Can Teach Us About The Game of Life
If any player in history exemplified this chapter, it is Mariano Rivera. Rivera’s cutter is arguably the most dominant single pitch in the history of baseball. But before he discovered the cutter by accident in 1997 (see the awesome video below), Rivera was a failed starter.
Incredibly, on June 11th, 1995, the Yankees sent both Jeter and Rivera back to the Minors on the same day. Both had been called up in May. In 50 plate appearances, Jeter had an OPS of .620.
Rivera was even worse. In four starts, he had allowed 17 earned runs in 15 innings for a 10.20 ERA and made it past the fourth inning in only one of them. The demotions were warranted. The decisions had not been made by the Assistant to the Traveling Secretary.
As the two consoled each other in a booth at a New Jersey Bennigan’s (which, let’s be honest, might have you questioning your life’s choices), Jeter turned to Rivera and said well we will just have to prove ourselves once again. Rivera was no stranger to proving himself, having worked 12-hour days in Panama on his father’s fishing boat and playing baseball with a cardboard glove. Jeter and Rivera brought those life lessons in perseverance, resilience, and self-belief to that New Jersey Bennigan’s. Rotbart and Davidoff’s book aims to impart them to the travel ball generation.
Success in life is often a matter of timing. Or in Davidoff’s case, a timeout. Perhaps the most famous timeout in sports history. Davidoff was covering the 1993 NCAA Men’s Championship basketball game from the stands for the student newspaper, The Michigan Daily. The biggest star of Michigan’s famed Fab Five, Chris Webber, got the ball with 11 seconds left and the Wolverines trailing by two. He signaled for a timeout. Unfortunately, the Wolverines did not have one, which triggered a technical foul, and the Tar Heels sealed the win from the free-throw line.
“Chris was dribbling towards me. I was behind that basket when he called the timeout. And I wrote the column on it for The Michigan Daily that night. Now, in retrospect, the column was terrible. I didn’t explicitly say Michigan lost the game. A sharp reader could infer it, but ideally, you should explicitly state that they lost. However bad the column was, though, it helped me get my first job at The News Tribune in Woodbridge, New Jersey. I had sent it s a clip with my application and the sports editor there Jim Miller said, ‘Tell me about this column,’ and I explained that I went to the press conference where Webber spoke, and then talked to some of the players in the locker room, and then I had an hour to write it, and I dictated it into the paper.”
Miller liked that Davidoff had covered a big game under real deadline pressure and hired him. A year later, he was at the Bergen Record and climbed the ladder from covering high school sports to college sports to, by 1998, covering the New York Yankees. The Yankees were in the midst of winning four World Series titles, but it was one they did not win that made the biggest imprint on him personally.
It was the 2001 World Series, just a month after 9/11. The Diamondbacks had taken the first two games in Arizona, blistering the Yankees by a combined 13-1 score. The series shifted to an emotional New York City for Games 3-5. George W. Bush, wearing a New York Fire Department windbreaker, threw a perfect strike for the first pitch of Game 3. The Yankees won that night, 2-1.
The next night, on Halloween, Tino Martinez tied the game with a two-run homer off Byung-Hyun-Kim in the 9th, and Derek Jeter earned the nickname Mr. November by hitting a game-winning walk-off just after midnight on November 1st.
The following night, Kim yielded another two-run homer in the ninth to tie it. This time, the hero was 34-year-old #8 hitter Scott Brosius, in his final season. Brosius had started the year as the #9 hitter and did not move up to the 8-hole until mid-May. Seeing the fans digest the Yankees’ improbable comebacks through the prism of 9/11 was one of the most emotional moments of Davidoff’s long and storied career.
Most of the time, though, he was a hard-hitting New York beat writer and columnist. And that sometimes involves friction with players.
“The one I most recall was Matt Harvey. He was addicted to headlines. He had Tommy John surgery after the 2013 season, and he kept saying he would be back in 2014 and made a big deal about doing his rehab in New York. 2014 was Jeter’s last year, and Harvey attended his last game as a fan when the Mets also had a game that night. Now, maybe I am old school, but it was not good optics. And so I wrote a column ripping him.
“I compared him to Curt Schilling and said something to the effect of, as long as he can pitch like Schilling, he will be fine, but that he has really been a pain in the ass. I then asked him a question when he came back, like, ‘You really made it about yourself last year.’ And he really did not like that. He gave me the death stare, and later in the year, he had a few more words for me because that was the year he threatened to pull out of the playoffs (he was concerned about injury by going over an innings limit).
Davidoff wrote about the innings limit that it was, “all about Harvey wanting it both ways and being a nuisance both ways. He surely increased Advil sales among Mets employees with his incessant whining.”
Davidoff repeatedly skewered Harvey’s maturity, professionalism, and accountability.
“Frankly, I don’t think I would have been doing my job well if I didn’t have a few run-ins with players”, Davidoff said.
There are many other players, though, whom Davidoff built strong relationships with, which he cites as the most rewarding part of his job as a sports writer. One he cherishes is David Wright, who wrote the foreword to 101 Lessons from the Dugout.
“David Wright is one of the finer people I have met in any walk of life,” Davidoff said.
Others with blurbs on the back of the book singing it and Davidoff’s praises include Joe Girardi, Bernie Williams, the Michigan softball coach Carol Hutchins, who is the winningest softball coach in NCAA History, and Mr. October himself, Reggie Jackson.
Jackson also includes special praise for Davidoff.
“I’ve always looked at Ken Davidoff as a person who cares about the game and about the people he writes about. For me, Kenny took an interest in the player, the game, how it was supposed to be played, and how it was supposed to be reported to the fan.”
In Chapter 11 of the book about personal and family crises, Rotbart and Davidoff write, “If you get sick, know that your family, friends, doctors, and nurses are all on your team, in the dugout with you — you are not fighting alone.”
For DiSavlo, Davidoff has been one of those friends with him in the dugout after a double lung transplant.
“Ken came over to my house on a Friday to see how I was doing, and on Monday, I was rushed to the hospital,” DiSalvo shared. “He has kept in touch with me from a personal perspective. It means a lot when folks are reaching out in the darkest hours. And that’s the kind of guy he is.”
Davidoff now has more time to be a loyal friend. As a teacher and author, he can also share the lessons he learned from his days covering baseball without needing his track shoes to chase down The Boss.