The life of being a professional athlete can cause even the most grounded of players to get swept up in all of the chaos. With this in mind, they often find themselves in tough situations in their post-playing careers due to poor decisions made while they were playing.
This is not the case for former New Jersey Nets forward Bobby Simmons, who is using the skills and connections that he developed throughout his playing career to his benefit now that he has retired from the game of basketball.
In an interview with Nothin’ But Nets, Simmons, now the owner of a variety of business including fashion boutique Bryson Milan
in his hometown of Chicago, detailed how he deepened his connection with the Windy City by staying at home to play in college at DePaul.
“It was exciting to have the opportunity to play the game I love with two other guys that I grew up playing with. It was great to be able to give the people of Chicago an opportunity to come out and cheer for guys that were from the area, too,” Simmons said.
His college career took off out of the gate and by the time his junior season came around, he was averaging over 16 points per game. Despite his success at the collegiate level, Simmons had eyes on the pro game.
After teammate Quentin Richardson entered the draft in 2000, Simmons decided to throw his name into the ring, a decision that he felt was one of the toughest he had to make at that point in his life.
“I think it was a tough choice because of how close I was to getting my degree. When I looked at it from an on-court view though, I was wondering if my game would get any better by staying an extra year in college and I believed that I was ready to take the next step.”
With a plethora of high school and international prospects entering the draft pool in this particular year, Simmons’ professional landing spot was up in the air even as draft day had neared.
For someone with the career that he had throughout his time at DePaul, Simmons was forced to wait what seemed like an eternity until he was selected with the 41st pick in the draft by the Seattle SuperSonics (which was later traded to the Washington Wizards).
“I was happy to be drafted, but I have to say that it was an incredibly long day and I thought that it wasn’t going to end. You never realize how long it takes to go through 41 draft picks until your future is decided by it. Regardless of whatever team I was on though, I knew the task at hand and knew that I was going to be successful wherever I went.”
With the anxiousness of the draft behind him, Simmons was ready to get back to what he knew best: playing basketball. After training camp and the preseason had come to an end, he was able to step on an NBA court for the first time in a game against the Atlanta Hawks.
“Just putting on the jersey then getting your name called and stepping onto the court was a dream come true. There’s millions of kids around the country that wish they could be able to do that and it was really the best feeling in the world.”
While he had been a star for the Blue Demons, Simmons found himself receiving intermittent playing time with the Wizards. While he hadn’t had the chance to show what he could do on the court, the connections that he made off of it would pay dividends once his career had come to an end.
“Michael Jordan had a big influence on me not only as a teammate, but also as a mentor and as someone that I looked up to. There’s something about him that you wouldn’t be able to get anywhere else and I was lucky enough to have two seasons to be able to experience him as a teammate and soak up as much knowledge of the game as possible.”
He continued, “He helped me learn how to build my brand as I played and I feel that is what is important to help players transition to their post-playing careers. It’s all about what you’ve built while you’re playing.”
Following the completion of his first season in the league, Simmons was hit with the reality of the business side of basketball. He was traded to the Detroit Pistons in a deal involving Jerry Stackhouse and Richard Hamilton, but returned back to the Wizards a couple of weeks later after having been waived by Detroit.
With this in mind, he played out the year in Washington but looked for a bigger opportunity elsewhere at the end of the season. That opportunity came with the Los Angeles Clippers, a team owned at that point by the infamous Donald Sterling.
“He wasn’t a guy that was always around. We would see him on gamedays and we would see his wife, Mary, and she was just the best. He wasn’t really someone that you would sit and talk to, he wouldn’t ask basketball questions, he wasn’t very vocal and I really didn’t have too much interaction with him. I think he respected everybody in the locker room and if he had issues that he was dealing with on his own, he didn’t really make them apparent.”
Off the court interactions aside, Simmons was able to see a bit more playing time with the Clippers during his first season, but his game was taken to the next level as the following year rolled around.
An early injury to veteran Kerry Kittles opened a spot in the starting lineup and Simmons pounced on it. Averaging 16.4 points per game on 46% shooting, he was named Most Improved Player at the conclusion of the season.
“I tip my hat to Coach Dunleavy because I think the big step was just him believing in me. I worked hard through training camp and the team was trying to fill the void that was opened. Coach Dunleavy asked Elton Brand and Corey Maggette how they should fill that void and they recommended me. That was the opportunity that I had been waiting for my whole career.”
His breakout year couldn’t have come at a better time, as his contract ended after that season. For a player that was traded after his rookie season, Simmons had teams beating down his door for the chance to sign him.
“It was really a bit overwhelming as someone that hadn’t been through it. After being drafted at 42, traded after my first year and then now I was up for a big contract, it was a lot to take in all at once. Meeting with all the teams throughout the summer, we were coming up on the CBA expiring so that meant a potential lockout, so there was a lot to deal with and a lot of pressure.”
Ultimately Simmons chose to ink a five-year deal with the Milwaukee Bucks, who had just retained Michael Redd and had drafted Andrew Bogut with the first overall pick just a couple of weeks before. The team was shaping out, but what convinced Simmons on the deal was his proximity to Chicago.
“I wanted to be closer to home so that my grandparents and parents could travel easier and so that my kids had the opportunity to actually watch their dad play. It was a great fit for me and I was glad they gave me the opportunity.”
He was able to maintain the success that he had in Los Angeles and further added a three-point shot to his game, shooting 42% on over three attempts per game, and the Bucks made it to the playoffs just one year after winning 30 games.
Heading into the following season, Simmons and the rest of the team were hoping to build on their success. In the offseason, however, his career and life, took an unexpected turn.
“After we had made the playoffs in Milwaukee, I was looking forward to following that up and but then I had an ankle injury. It didn’t happen in a game and it was really something that came on all of a sudden. We had four or five doctors trying to figure out the issue and I went all over the US to get an answer about why it was happening. When I eventually got surgery, I was told that I was never going to play again since it was an injury that they had never seen.”
With his career now in question, Simmons began making moves towards his post-playing career even though he was just 26-years old. With that brand that he had built to that point, he chose to start a business in his hometown.
“I was trying to figure out what I wanted to do if I couldn’t play again since basketball was all that I really knew. I started trying to figure out something I was interested in and being a Jordan athlete, I liked sneakers and I was familiar with real estate from the courses that I had taken in college, so I thought, ‘What if I open a store in my hometown?’ In the summer of 2007, I opened my first store called Succezz and it’s a sneaker boutique in Chicago that has been running for 8 years strong.”
With his career off of the court taking off, Simmons was able to return to basketball despite the initial prognosis. After one more season in Milwaukee, Simmons was shipped off to New Jersey that also sent Yi Jianlian to the Nets.
“I think with myself and Yi being traded, we helped each other out as far as knowing how to play together and helping each other learn the new system and fit into the group. We had Vince Carter, Devin Harris, Chris Douglas-Roberts, Courtney Lee, Brook Lopez and some other young guns that looked to us to help them out.”
He went on, “It was a learning experience that as you get older you start to teach the game more as opposed to playing the game. A lot of guys are very talented, but don’t understand the right way to play.”
After two seasons in New Jersey and a brief stop in San Antonio, Simmons returned to Los Angeles to help the Clippers down the stretch as they headed into the playoffs.
Once the Clippers were bounced out of the playoffs in the second round, Simmons chose to move to his business ventures full-time. Succezz was his start into the entrepreneurship world, but he’s only managed to grow from there.
“I have started the Bobby Simmons Rising Star Foundation, which grants 10 scholarships per year for students in Chicago to DePaul University. I started a real estate investment company called Monarchy, a nightclub called Society 2201 and a printing company called Full Spectrum Printing.”
In addition to the efforts that he’s made in those areas, his work with Bryson Milan has allowed him to pursue his interest in the fashion world.
“Given that Chicago is huge for fashion, I often saw people buying expensive clothes just for the name on the label. With Bryson Milan, we’re making stuff out of the same fabric for both men and women for a much more feasible cost to the customer. We want people to be dressed well for any type of event and we don’t want it to cost them an outrageous amount of money.”
The connection that he had developed in Washington with one of the game’s all-time greats has served to propel his business career, too. Through the advice that he gave them in their playing days and the contact that they’ve kept, Simmons has been aided by one of Chicago’s legends.
“In all of the things that I’ve done in business, it’s helped that Michael Jordan was my mentor and I could bounce questions off of him regarding the structure of the business and things of that nature whenever I needed it.”
With the success that he has managed to have in his business career, Simmons is now turning to help others in the situation that he was once in. Now a career counselor for the NBA Player’s Association, Simmons hopes to put current players on the track that Michael Jordan once set him on.
“I inform these guys that they should use the opportunity of playing on the big stage and meeting whoever they want to meet to their advantage in their off-court career. If they take advantage of these opportunities, they might want to venture out and explore some of their interests once their playing career is over. A lot of times guys can get taken advantage of when people tell them what to do and how to spend their money rather than the player just doing what he wants to do and pursuing what he’s interested in.”
A Most Improved Player during his basketball career and a success in the business world, Bobby Simmons is a case study of how to use the platform of professional athletics effectively even once an athlete’s playing days have come to an end.