32 books like Playing for Keeps

An 11-time NBA champion, Bill Russell revealed the insecurity of being a super tall, lanky, Black man that can’t avoid notice. He wrote honestly about racism and civil rights in America. He mentioned great Celtics players and described the NBA’s early days. His description of the physical demands of traveling and playing so many games made me realize his job was hard work. Read it just to find the passage where Russel describes—better than any writer ever has—that rare, amazing feeling you get when teammates are in sync, everything is clicking, and a team plays at its peak.

I wholeheartedly embraced this book by Roland Lazenby. It's a slam dunk of a biography that left me in awe of Jordan's unparalleled drive and impact. I was captivated by Lazenby's masterful storytelling, which brought MJ's journey to life in vivid detail. I found myself completely immersed in the highs and lows of Jordan's career, from his early setbacks to his iconic championships.

What I appreciated most was how Lazenby delved beyond the court, offering insights into Jordan's personal struggles and business acumen. This book deepened my admiration for Jordan, not just as a player but as a complex individual who reshaped sports culture. I couldn't put it down and came away with a newfound appreciation for the man behind the legend.

I love when sports stories intersect with broader cultural movements. Those instances are what make sports matter. Elgin Baylor was an amazing basketball player, but he was also a civil rights icon. Learning more about that work is just as important to me as learning about his games, and Bryant’s work makes it so exciting to learn about.

This book is a graphic novel, giving Baylor’s story access to a much larger audience. I am not normally a consumer of graphic novels, but this one does the story justice and is so good. Even as someone who doesn’t normally embrace the genre, I loved it.

As avid readers and sports lovers likely already know, Pearlman is an amazing storyteller, and he perfectly captures the drama and craziness surrounding the Lakers dynasty from 1996-2004, defined by the dynamic duo of Kobe and Shaq.

This book is packed with details and insights—gleaned from hundreds of interviews and extremely in-depth reporting—that kept me engaged from start to finish.

Fader’s book presents a side of Milwaukee Bucks superstar Giannis Antetokounmpo that I never knew about, focusing less on his stellar NBA career and more on his family and all the hardships he has faced, from growing up in immense poverty to grappling with his identity to struggling to adjust to life in America.

Through outstanding reporting, Fader tells a story that is both heartfelt and inspiring in ways I didn’t expect when I first dove in. This is one of my favorite books ever. 

Ray Scott is a living bridge from the first generation of Black players in the NBA to the modern NBA that emerged in the 1970s.

Through high school in Philadelphia where he played against Wilt Chamberlain, to college in Portland where he first competed against Elgin Baylor, to his formative professional years in the Eastern League where his contemporaries were the league’s all-time stars like Sherman White, Wally Choice, and Hal “King” Lear, to his early years in the NBA where his mentor was Earl Lloyd, to succeeding Lloyd as an NBA coach and becoming the first African American named NBA Coach of the Year, Scott has soldiered through numerous affronts yet always emerged with grace, dignity, and hope.

“Coach,” as he is called, in this memoir written with prolific basketball writer and former Eastern League player Charley Rosen, demonstrates why he is respected and beloved as both a leader… show more.

Bill Bradley was as far from a typical college and NBA superstar as can possibly be imagined. He was 6’5” but could barely dunk. In a race between the tortoise and the hare, he would be the tortoise. Yet, with an uncanny set of shooting, passing, and rebounding skills, he became the nation’s top high school prospect, with more than 70 colleges, including every powerhouse in the sport, offering him a scholarship. Instead, he chose to play at lowly Princeton, in one of the game’s weakest conferences—the Ivy League—where he averaged more than 30 points a game over the course of his career, becoming a two-time first-team All-American and, in his senior season, national player of the year, leading the Tigers to the 1965 NCAA tournament’s Final Four, in which he scored an unheard of 58 points against Wichita State and was named the tournament’s MVP—the only player to this… show more.

I rushed out to buy Kriegel’s bio of Pistol Pete when it hit stores in 2007.

I’d always found Maravich fascinating as a basketball player—the guy is still the all-time leading scorer in Division I men’s basketball history, and he played just three years of college ball—but didn’t know much about his life.

I wondered: How was there enough material for Kriegel to write a full-length book about him? Turns out, more than enough for Mark to write a brilliant book that, like so many great sports stories, is really about fathers and sons.

In this thoughtful, philosophical autobiography, the winningest player in NBA history uses his storied career with the Boston Celtics as a cogent window into the broken promises—mostly racial—of the American Dream. Co-written with historian Taylor Branch, whose trilogy on the life of Martin Luther King, Jr., won the Pulitzer Prize, Russell, who has devoted as much of his life to activism in the cause of social justice as to the game of basketball, shares the life lessons he has learned on the court, from his schoolboy days in Louisiana to his All-American stint at the University of Seattle, to his record-setting career with the Celtics, where he won an astounding eleven championship rings in thirteen years. This book was published in 1979, but its insights are as relevant and penetrating today as they were then.

A great book about leadership and business. I pick it because it’s on the reading list suggested in The Art of Profitability. I learned that focus is important. Bill Russell was one of the greatest basketball players of all time because he worked harder and played smarter than everyone else. However, he also recognized that he doesn’t play every position. He needs to have a great team, one that adapts to the competition. He needs them all to play at his level and he was able to do that, winning the NBA Finals a record-breaking 11 seasons. One way to build a successful side hustle (or portfolio of side hustles) is to recruit a great team to help you.