It may surprise people to find out that former professional basketball player James Singleton played more chess than basketball growing up. The recently hired coach brought his love for the chessboard to the way he lives his life — accomplishing one move at a time, while constantly calculating the next.

Singleton was born in 1981 on the south side of Chicago, a community with a reputation as one of the most dangerous in the nation. Growing up in the middle of gang violence and substance abuse, Singleton had only one goal: escaping. In high school, he saw his childhood friends join gangs. They abused drugs and alcohol.

Singleton was determined to avoid that. He never gave in to peer pressure and got into fights over it.

“That’s the quickest way to six feet under,” Singleton said.

While serious about some things, the young teen was free spirited, a class clown who didn’t take life seriously. Early on, he was smaller and played some sports, but mostly chess. Anyone looking at a young Singleton would never have expected him to have planned to use sports for his future, but he knew basketball was his only option besides joining a gang.

“Chess helped me understand you have to take it one step at a time, plan ahead, and when you get the opportunity, checkmate,” Singleton said. “My checkmate was getting out of there.”

When he had his growth spurt to 6 foot 6 inches his sophomore year of high school, he suddenly had an escape route.

In 1999, Singleton was 6 foot 9 inches and graduated highschool with a scholarship to Pearl River Junior College. He realized his hard work paid off, as he had another chance that he wasn’t going to waste.

However, in his first year at Pearl River, Singleton tore his ACL while trying to get a rebound. He lost multiple offers from other colleges. With schools turning their backs on him, it seemed his future had flatlined.

“Because teams thought I was done, I thought I was too,” Singleton said.

For the first time in years, Singleton gave up on himself. He planned to go back to Chicago.

However, his coach at the time, Richard Mathis, pushed Singleton to continue. Every morning at 6 a.m, Mathis dragged Singleton to the weight room for rehab with a cup of coffee in his hand, a banana and newspaper in the other.

“That is burned into my nose for life,” James said. “Everytime I walk into a weight room I smell coffee and bananas to this day.”

A year and a half later, he got back on the court and had a great season at Pearl River. In his junior year, he transferred to Murray State, a D-1 college with a renowned basketball program.

At Murray State, Singleton led the Racers to the Ohio Valley Conference title and played in an NCAA tournament. Due to his college success, Singleton got a call to play in the Legadue, an Italian basketball league. Singleton knew playing overseas could put him on a path to the NBA.

“Being from Chicago, I played against NBA players every summer, so I knew I could play with them mentally and physically,” Singleton said. “…The only way for me to get an opportunity was to dominate wherever I went.”

Singleton also saw moving to Italy as a way to see what the world was like outside of Chicago.

“You see these things on television,” Singleton said. “You read it in books but you don’t see it from someone else’s perspective. I wouldn’t trade that for anything.”

In Singleton’s first year in Europe, he averaged stats that caught the attention of the NBA. After two great seasons in Italy, Singleton signed with the Los Angeles Clippers in 2005 and played there for two years.

He had climbed every level from high school, to college, to Europe, finding a way to play for the NBA. In that moment, he only had one thing on his mind — success. Singleton was enjoying it, but knew this was just the beginning.

“Now I have to work even harder,” Singleton said. “Getting there was the easy part. The hard part is maintaining being there.”

Singleton gained attention from teams worldwide, including Spain’s team TAU Vitoria, now known as Saski Baskona. He signed to play there for the 2006 season, becoming the highest paid player in Spain and gaining a lot more playing time.

But during a game, Singleton got hit while attempting to dunk and landed awkwardly. He felt a surge of pain in his knee. He knew he tore his ACL again.

Back at Pearl River, Singleton had no idea how he was going to get through it and almost abandoned his dreams. However, this time there was no feeling of despair. He was going to do it, one move at a time.

The local media called Singleton, asking about the injury.

“I’m not done. You’ll be seeing me in five to six months,” Singleton said.

The interviewer said there was no way he could come back from a full ACL tear and play that season.

Singleton disregarded the comment. He was sure he could do it.

• • •

Four and a half months was all it took.

During practice, Singleton dropped his crutches to jog with his team. They yelled at him to stop and the trainer chased him, but Singleton was stubborn. He knew where his body was at, and he needed to prove himself.

He was given five minutes to play in their next game, but ended up playing 22. Singleton was back and nothing was going to stop his team. TAU Vitoria played Barcelona in the League’s Finals, beating them 3-0.

“That championship meant more to me than anything,” Singleton said. “Not only did I get over personal adversity, I went against all the odds.”

Singleton returned to the NBA in 2009, playing for the Dallas Mavericks, the Toronto Raptors and the Washington Wizards.

During his time on the Mavericks, Singleton played with Dirk Nowitski, a Texas legend. The two had a rivalry since they played each other years ago. Every day, Nowitski and Singleton competed to see who could shoot a certain number of baskets first. Singleton did everything he could to beat Nowitski.

“Dirk had a different gear when it came to shooting,” Singleton said. “I say we shot against each other about 500 times. I never won once.”

Singleton was later traded to the Washington Wizards, but being able to play with Nowitski was an incredible learning experience.

“I give that man nothing but credit for everything he helped me out with my career,” Singleton said.

• • •

Singleton spent his last couple years in the NBA bouncing between China and the Wizards. After leaving the NBA, Singleton played overseas in China, Israel and South Korea, where he was a player-coach.

“I wanted to come and coach on the court,” Singleton said. “I’ve always had a passion for it.”

Singleton interviewed for a coaching position with the NBA’s minor league, the G League. He was hired by the San Antonio Spurs’ G League team the next day.

Singleton was nervous to begin coaching. He knew some of the players like Kawhi Leonard and Lamarcus Aldrige, but now Singleton was coaching them.

Early on in practice, Spurs Head Coach Gregg Popovich asked Singleton to guard players. He was 6 foot 9 inches and could still move like an athlete, giving him an advantage over the majority of the other coaches.

“That was huge for player development,” Singleton said. “Because not only can I tell a guy to do something, I can get out there and show him.”

Singleton was anxious to look for a head coaching job after two years with the Spurs, but realized he had more to learn. He began training any player that wanted it, no matter their skill level, to learn about player development.

• • •

Last spring, Singleton talked with Head Basketball Coach Shane Rogers about the vacant spot as the varsity assistant coach. While coaching always came naturally to Singleton, he would also be teaching world history, an entirely new experience to him.

“I was a jack of many, master of none,” Singleton said. “But I’d always done basketball camps, training, coaching, so I said, ‘Cool, I’ll figure this out.’”

Now into the season, Rogers appreciates how valuable having Singleton on the staff has been.

“I feel like James has been an unbelievable addition to us and what we were already doing,” Rogers said. “I think we had this program headed in the right direction… and James has been a great addition to that.”

Rogers said the most valuable of all has been Singleton’s dedication to his day-to-day responsibilities.

“For him to be willing to come up here early in the morning, and stay late some nights, sacrificing time away from his family, it just shows how good of a guy he is and what he’s willing to do to help others,” Rogers said.

Senior point guard Jalen Lloyd said the entire team sees Singleton as a source of knowledge on how to get to the collegiate level.

“It definitely helps a lot for someone who’s been there and beyond to tell you exactly what you need to fix and what to work on,” Lloyd said.

After he officially joined the school’s coaching staff, many people wondered why Singleton would take a major pay cut from being an NBA coach to a high school one.

“I’m not here for the money,” Singleton said. “I’m here because A. It’s close to home, and B. Marcus is a 6A school, which means it has an outstanding program.”

Most of all, he decided to coach high school to spend more time with his family. He has two sons and a daughter, who he missed while playing professionally.

“I saw my [oldest] daughter’s first steps via Skype,” Singleton said. “I missed a lot, and I wasn’t going to miss another moment.”

This story was originally published on The Marquee on February 22, 2021.