See, almost a decade ago, Conner's playing career was over and he wasn't sure what he wanted to do next, other than get married. But a shopping trip, a chance meeting and an unexpected connection opened the door to his second life.
"Going into coaching, it was really like a fluke or luck," Conner said. "It wasn't something that was planned, it just kind of happened.
"I was buying my wife's wedding ring from Rick Pitino's best friend, a guy named Joe Iracane, but at the time I didn't know that. Over the course of the business transaction, he took a liking to me and said he had a friend who might be able to do something for me down the line. I was like, 'Do you mind he asking who your friend is?' And he said, 'Rick Pitino.' "
One thing led to another and Conner wound up on Pitino's staff for the 1999-2000 season. When Jim O'Brien replaced Pitino midway through the following season, Conner stayed, thus beginning a long relationship. Conner, who remained with O'Brien through the Boston years and on to Philadelphia, has rejoined him with the Pacers.
"He's like a father figure to me," Conner said. "He genuinely cares about my welfare off the court. He's taught me some things about life. He's taught me some things about family. He's taught me some things about relationships with people. He's taught me about being forgiving. He's taught me about finances. He's taught me about being a better husband, about being a father once I became a father. I've learned so many things other than basketball."
The admiration is mutual. O'Brien has groomed Conner to become a head coach and believes he's qualified to take that next step. Conner's role on the current staff will be multi-faceted, including developing the younger players while contributing to both the offensive and defensive preparation.
"Lester and I have been together for a long time and he has really come a long way as a basketball coach," O'Brien said. "Lester is going to coach our summer-league team because he has the ability to be a great head coach. I see a lot of people in the NBA that are applying jobs that do not have the type of background Lester has developed. As a player, he played for a number of fine head coaches. As a coach, this will be his fourth franchise.
"He's a great communicator, thoroughly understands every aspect of the game and is a tireless worker. These are all ingredients that will lead to him becoming a very fine head coach in the future."
Though Conner's name may not resonate with Pacers fans, he was part of perhaps the most dramatic time in the franchise's NBA history: the amazing run through the end of the 1993-94 regular season that lasted into the Eastern Conference Finals that turned out to be the beginning of a decade of residence among the ranks of the elite.
Conner, who played for seven teams in a 13-year career, was nearing the end when he signed with the Pacers in April of '94. In fact, after less than two weeks with the team, he felt it was time to retire.
"In my mind, it had come to be that my career was over," he said. "I'll never forget this. I went to Larry Brown in Minnesota and told him I thought it was time for me to take off because I thought my career was over. He wanted me to stay. He said, 'Lester, guys like you are important. You're an important leader, the guys listen to you.'
"I remember Byron Scott and Reggie Miller coming down to the room to talk me into staying and there were some tears shed. It was a real emotional time. My girlfriend at the time, who is now my wife, had flown to Indianapolis to get all my stuff from the hotel. They ended up talking me into staying and I had a wonderful time. … That team was so close. "
In addition to friendships with Miller and Scott, Conner was and remains close with LaSalle Thompson, who recently moved back to Indianapolis and runs a real estate investment company. He shared an agent with Kenny Williams, and grew close to fellow Oakland, Calif., high school product Antonio Davis.
Now he is back, in a different sort of leadership role and still in the early phase of a relatively new career.
Before too much longer, you'll begin hearing Conner's name mentioned when coaching vacancies open up, because he appears to be very much a star on the rise.