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The Life of an NBA Player Manager

Randy Osei’s dream of playing in the NBA didn’t come to fruition, so he turned to player management.

Oliver Maroney



The NBA is thriving and, as a business, is more lucrative than ever. While this means more money for the owners, players, executives and coaches within the league, it’s also excellent for individuals like Randy Osei.

Osei works in player branding and management, which is a booming industry these days since players possess a wide variety of ways to earn additional income beyond their NBA contract.

His company, Rozaay Management, counts Milwaukee Bucks forward Thon Maker and Brooklyn Nets forward Anthony Bennett as clients. Osei helps them with marketing, endorsement deals, public relations and much more.

Most player managers have an extremely broad set of skills and they must wear many hats. One night they could be negotiating an endorsement deal, the next they could be helping a player with a community event. Osei’s job is to help his players with whatever they need, which can vary greatly from client to client.

Managers like Osei are often extremely involved in a player’s life and are integral to their success, yet they are unknown to even the most diehard NBA fans. They aren’t visible like the player’s agent and they aren’t in the background like a hanger-on. Instead, they handle a certain set of off-court responsibilities and, in Osei’s case, are paid by the player.

So how does one end up working in player branding and management? A former basketball player with his own goal of playing in the NBA, Osei didn’t initially have this career in mind.

“I just love the game of basketball,” Osei told Basketball Insiders. “I had dreams of playing in the NBA or even overseas professionally. But due to many injuries, I decided that I wanted to impact the game off the court.”

However, that decision wasn’t made overnight. Osei was actually going to college and working toward a degree in Sociology and Psychology, which was taking up most of his time. It wasn’t until he spent a few weeks with Cleveland Cavaliers forward Tristan Thompson that he realized he wanted to take his life in a different direction. In a bold and risky move, he dropped out of school and decided he wanted a career that allowed him to remain around basketball.

“I made up my mind that I wanted to work with NBA players,” Osei said. “I didn’t graduate. Against my Mom’s wishes, I left school early.

“I came into this business as Anthony Bennett’s manager. I am a few years older, but Anthony and I were pretty close after playing on the same AAU team. I learned a lot in my first year with the former No. 1 overall pick. I found a lane where I thought I could excel, and I pursued it. I didn’t know how to get started, so I just took it upon myself to do the thing that many people fail to do: just start. I read everything and anything; Google became my best friend. I decided that I wanted to be more than just Anthony Bennett’s ‘guy.’ After three years, my passion became my full-time job and I haven’t turned back since.”

Since diversifying and working with players outside of Bennett, he’s become very successful. Many players look to him as their go-to guy for marketing, endorsements and event planning. In addition to his full-time work with Bennett and Maker, he has worked on various projects with Charlotte Hornets point guard Kemba Walker, Portland Trail Blazers guard C.J. McCollum Minnesota Timberwolves swingman Andrew Wiggins, Orlando Magic forward Aaron Gordon and Indiana Pacers forward Georges Niang among others. With that said, he has also resumed taking online classes toward his degree because he understands how important his education was in getting him to this point.

“Rozaay Management has been great in connecting me with some really cool brands, and has put together some events for me and my brand,” Wiggins said. “Dating back to All-Star Weekend 2015, Randy put together two events to help push my brand at my first All-Star Weekend experience.”

“Randy is great; he has helped me understand that I am not just a basketball player, but I am also a brand myself,” Niang said. “I am very appreciative of the work he has done with me.”

Some of the biggest events involving players have come from Osei’s promotional planning and marketing expertise. He’s built relationships with many NBA agents and players, establishing connections that have yielded opportunities as well as lifelong friendships.

“I’m passionate and want to do the best for everyone,” Osei said. “I am a strong believer in myself and I look to grow a little more each day. Within that growth, I see the importance of growing relationships. My relationships with athletes, entertainers and brands are genuinely organic. This is something that I find very important. Every bridge I gap always works great for both parties. Within that, I am able to cross reference a lot of opportunities.”

Osei is quickly becoming a well-known commodity. He has proven his ability to use social media and word of mouth to plan and promote large NBA-related events. One recent event he hosted in Toronto during the All-Star break had such a huge crowd that he had to turn away some players and celebrities.

“I lived in Cleveland and Minnesota,” Osei said. “I was able to connect with a lot of players. But after moving back to Toronto, I realized I could add another service to my company as a player liaison. When guys came to town, I’d take them around to all the great places in Toronto. All-Star Weekend happened to be in Toronto last year and I said, ‘Why not throw an event on Thursday evening of All-Star Weekend?’ It turned out to be the best event of the entire weekend. The event reached capacity quickly and I ended up having to turn away the likes of Allen Iverson, who happens to be one of my favorite players of all-time. That crushed me.”

Utah Jazz point guard George Hill has used Osei’s liaison business and was satisfied.

“This past year while we took on the Raptors in the first round of the playoffs, Randy showed me all the great things to do in my downtime while in Toronto,” Hill said.

Osei, who is always looking to launch new endeavors, recently created a YouTube series called “Rozaay TV” that features NBA players. The series gives a behind-the-scenes look at each player’s life, including their workouts and off-court activities.

Houston Rockets point guard Tyler Ennis, who has known Osei since middle school, was recently featured on the series.

“I’ve known Randy since I was about 13,” Ennis told Basketball Insiders. “I’ve seen the growth from him just being around the game to creating a lane and a business for himself. He works extremely hard on every project that I’ve been involved in. He just gets things done.”

Osei has gone from college dropout to managing numerous off-court endeavors for NBA players. Now, Osei is hoping to use his skill set and relationships to help people who are less fortunate in Ghana, the country where his parents were born.

“In my 26 years of living, I had never gone back to where my parents were from,” Osei said. “The first day I arrived in Ghana, I teared up seeing the place my parents grew up. Driving through the towns and villages, you see the struggles that people have and it truly broke my heart. Every time you stop at a traffic light, kids will walk up to your car to sell you whatever they have.”

While the trip was to visit his parents’ country, he decided he would like to make a difference there and also help spread the game of basketball.

“I got to check out the local basketball talent,” Osei added. “It was awesome to see the sport being so global. Almost all the kids were long and athletic, but lacked the fundamentals of the game. Basketball is not offered in elementary schools or high school, so there is no real development. Nine million dollars a year is dedicated to sports development, but 92 percent of that is dedicated to soccer. My goal is to go back and help change that.”

This is why Osei has been so successful. Not only is he talented at his job, he genuinely cares about the people he comes in contact with, develops meaningful relationships and has a strong desire to help others – whether they’re childhood friends, potential NBA client or those less fortunate than him.

Oliver Maroney is an NBA writer for Basketball Insiders. He is based in Portland and covers the league as a whole.


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The Real Jrue Holiday Has Finally Arrived

It may have been a little later than they would have wanted, but the Jrue Holiday that New Orleans has always wanted is finally here, writes Matt John.

Matt John



New Orleans has always earned the nickname “The Big Easy”, but ever since Jrue Holiday came to town, his time there has been anything but.

When New Orleans traded for Holiday back in 2013, they hoped that he would round out an exciting young core that included Anthony Davis, Eric Gordon, Tyreke Evans, and Ryan Anderson. At 23 years old, Holiday averaged 17.7 points, 8.0 assists, and 4.2 rebounds the previous season and was coming off his first all-star appearance in Philadelphia, so the Pelicans had much to look forward to.

Unfortunately, recurring extensive injuries prohibited the Pelicans’ new core from ever playing together fully healthy, with Holiday getting his fair share of the bruises. In his first two seasons, Holiday played in only 74 games combined with the team due to injury, and things didn’t get much better his third season. While he played more games, Holiday was on a minutes restriction and his season ended again with injury.

Holiday avoided the injury bug his fourth season, but he nobly took a leave of absence at the start the season to tend to his ill wife, which caused him to miss the season’s first 12 games and 15 in total. Holiday’s inability to stay on the court coupled with New Orleans’ stagnated progress made him a forgotten man in the NBA. That was until last summer, when Holiday became a free agent.

Given the circumstances, Holiday did what he could for the Pelicans. He certainly proved he was above average, but he hadn’t shown any improvement since his arrival. Coupling that with both how many games he had missed in the previous four seasons and the league’s salary cap not increasing as much as teams had anticipated, and one would think to proceed with caution in regards to extending Jrue Holiday.

But the Pelicans saw it differently. New Orleans gave Holiday a five-year, $126 million extension last summer, befuddling the general masses. Besides Holiday’s inability to stay on the court, the Pelicans already had an expensive payroll, and they later added Rajon Rondo, another quality point guard, to the roster. So, with all that in mind, giving Holiday a near-max contract on a team that had made the playoffs a grand total of once in the Anthony Davis era seemed a little foolish.

This season, however, Jrue Holiday has rewarded the Pelicans’ faith in him and has proven the doubters so very wrong.

With a clean slate of health, Holiday has proven himself to be better than ever. This season, Holiday averaged career-highs in scoring (19 points a game) and field goal percentage (49 percent overall), which played a huge role in New Orleans having its best season since Chris Paul’s last hurrah with the team back in 2011.

Holiday’s impact extended beyond what the traditional numbers said. His on/off numbers from showed that the Pelicans were much better on both sides of the ball when he was on the court compared to when he was off. Offensively, the Pelicans had an offensive rating of 108.9 points per 100 possessions when he was the on the court compared to 104.4 points per 100 possessions when he was off.

On the other side of the court, Holiday was even more integral. The Pelicans had a defensive rating of 103.3 per 100 possessions when Holiday was on the court compared to 112.3 off the court. Overall, the Pelicans were 13.6 points per 100 possessions better with Holiday on the floor. That was the highest net rating on the team, even higher than Anthony Davis.

Other statistics also support how impactful Holiday has been this season. According to ESPN’s real plus-minus page, Holiday’s 3.81 Real Plus-Minus ranked ninth among point guards – No. 16 offensively, No. 4 defensively – which beat out Kyrie Irving, John Wall, and Goran Dragic, all of whom made the All-Star team this year.

However, Holiday’s effectiveness shined through mid-way through the season, or more specifically, on Jan. 26, when Demarcus Cousins went down with an Achilles tear. While Davis certainly led the way, Holiday’s role could not have been understated when the Pelicans went 21-13 without their MVP candidate to finish the season. Offensively, Holiday’s point average went from 18.6 to 19.4 and his assist average went from 5.2 to 7.2, all while his turnover average – from 2.6 to 2.7 – stayed the same.

Defensively, Holiday had much to do with the Pelicans’ improved defense after Cousins went down. According to, the Pelicans defensive rating went from 106.2 points allowed per 100 possessions to 103.7, and much of it can be attributed to Holiday. When Holiday was on the court, the team’s defensive rating was 101.2 points allowed per 100 possessions compared to 109.6 points allowed per 100 possessions with him off.

Holiday’s improved numbers, combined with the Pelicans steadying the boat without their star center, make a fair argument that Holiday was one of the league’s best all-around point guards this season, but Holiday’s style isn’t much of a thrill to watch. He doesn’t have Russell Westbrook’s other-worldly athleticism, he doesn’t have Stephen Curry’s lethal jumper, nor does he have Chris Paul’s floor general abilities. Holiday’s specialty is that he has every fundamental of a good point guard, which makes his impact usually fly under the radar.

That was until last week, when the Pelicans unexpectedly curb stomped the Blazers. The Jrue Holiday coming out party was in full-swing, as the 27-year-old torched Rip City, averaging 27.8 points, 6.5 assists, and 4 rebounds a game on 57 percent shooting from the field, including 35 percent from deep. He did all of that while stymieing MVP candidate Damian Lillard, as Dame averaged 18 points and 4 assists while shooting 35 percent from the field, including 30 percent from deep, and surrendered four turnovers a game.

If Holiday’s contributions weren’t on full display then, they certainly are now. The Pelicans have suddenly emerged as one of the West’s toughest and most cohesive teams in this year’s playoffs, with Holiday playing a huge role in the team’s newfound mojo and potentially glorious future.

This was the Jrue Holiday the New Orleans Pelicans had in mind when they first traded for him almost five years ago. While his impact has come a little later than they would have wanted, it’s as the old saying goes.

Better late than never.

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NBA Daily: Are Player Legacies Really On The Line?

How important is legacy in the NBA playoffs? Lang Greene takes a look.

Lang Greene



As the NBA Playoffs continue to pick up steam, the subject of individual greatness has become the big topic of conversation. Today, we ask the question: is legacy talk just a bunch of hyperbole or are they really made or broken in the playoffs?

To be clear, legacies do matter. Reputations are built on reliability and how dependable someone is throughout the course of their respective body of work. We all have them. They are built over time and it’s seldom they change from one misstep – but they can. Some of the greatest players in NBA history never won a title; see John Stockton and Karl Malone during their Utah Jazz years. Some NBA greats never won a title until they were past their physical prime and paired with a young charge that took over the reins; see David Robinson in San Antonio. Some NBA greats never won a title as the leading man until they were traded to a title contending team; see Clyde Drexler in Houston. We also have a slew of Hall of Famers that have been inducted with minimal playoff success in their careers; see the explosive Tracy McGrady.

So what’s in a legacy? And why does it mean more for some then it does for others?

Four-time League MVP LeBron James’ legacy is always up for debate, despite battling this season to make his ninth NBA Finals appearance. James’ legacy seems to be up in the air on a nightly basis. Maybe it’s because of the rarified air he’s in as one of the league’s top 10 players all-time or maybe it’s just good for ratings.

As this year’s playoffs gain momentum, the topic of legacy has been mentioned early and often.

Out in the Western Conference, the legacy of Oklahoma City Thunder All-Star guard Russell Westbrook is being questioned at all angles. There’s no doubt Westbrook is one of the best players in the league today as the reigning MVP and coming off two consecutive seasons averaging a triple-double. However, Westbrook’s decision making has come into question plenty over the past couple of seasons.

The subject of whether you can truly win a championship with Westbrook as your lead guy serves as the centerpiece of the debate. It goes without saying former league MVP Kevin Durant bolted to the Golden State Warriors amid rumors that he could no longer coexist next to Westbrook in the lineup. Ever since Durant’s somewhat unexpected departure, it seems Westbrook has been hell-bent on proving his doubters wrong – even if it comes at the detriment to what his team is trying to accomplish.

The latest example was in game four of his team’s current first-round series versus the Utah Jazz.

Westbrook picked up four fouls in the first half as he was attempting to lock up point guard Ricky Rubio, who had a career night in Game 3 of the series. Westbrook infamously waved off head coach Billy Donovan after picking up his second personal foul in the first quarter. Westbrook was also in the game with three personal fouls and under two minutes left in the first half before picking up his fourth personal.

You can make an argument that this was just bad coaching by Donovan leaving him in the game in foul trouble, but it also points to Westbrook’s decision making and not being able to play within the constructs of a team dynamic. Further, what will be Westbrook’s legacy on this season’s Oklahoma City Thunder team with Carmelo Anthony and Paul George if they were to flame out in the first round with little fizzle – against a Jazz team with no star power and zero All-Stars? Is discussing Westbrook’s legacy worthless banter or is it a legitimate topic? There is no doubt on his current trajectory Westbrook is headed straight into the Hall of Fame on the first ballot. As an individual player there is no greater achievement than to have your name etched in stone with the greats of yesteryear, but the court of public opinion factors in team success and this is where the topic of legacy comes into play.

Say what you will about Durant’s decision to go to Golden State, but his legacy is undoubtedly secured. Durant won the Finals MVP last season in absolute dominant fashion and showed up on the biggest of stages. All that’s left from those that question Durant’s legacy at this point are the folks on the fringe saying he couldn’t do it by himself. But that is exactly the line of thinking that’s getting Westbrook killed as well, because winning championships is all about team cohesiveness and unity.

Out in the Eastern Conference, all eyes will be on Milwaukee Bucks do everything star Giannis Antetokounmpo. After five seasons in the league, Antetokounmpo has zero playoff series victories attached to his name. Heading into the playoffs this season, the seventh-seeded Bucks were considered underdogs to the second-seeded Boston Celtics.

But the Celtics are wounded. They do not have the services of All Stars Kyrie Irving or Gordon Hayward. The Celtics are a team full of scrappy young talent and cagey veterans. Antetokounmpo is clearly the best player in the series and teams with the best player usually fare well in a seven game series. But the Bucks are facing elimination down 3-2 versus Boston. Antetokounmpo has only been in the league half of the time Westbrook has, but the chirping about his legacy has already begun as Milwaukee attempts to win its first playoff series since 2001.

So what’s in a legacy? Are there varying degrees for which people are being evaluated?

Despite James’ success throughout his career, a first-round exit at the hands of the Indiana Pacers over the next week will damage his legacy in the minds of some. While others feel even if Antetokounmpo and the Bucks were to drop this series against the Celtics, he should be given a pass with the caveat that he still has plenty of time in his career to rectify.

As for Westbrook, there are vultures circling the head of his legacy and these folks feel that a first-round exit will damage his brand irreversibly after 10 seasons in the league

Ultimately, the topic of legacies makes for good column fodder, barbershop banter and sport debate television segments. Because when guys hang up their high tops for good, a Hall of Fame induction is typically the solidifying factor when it comes to a player’s legacy.

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Insiders Podcast

PODCAST: The Futures Of LeBron, PG13, Kawhi and More

Basketball Insiders publisher Steve Kyler and NBA writer David Yapkowitz talk about the future of LeBron James in Cleveland, the Paul George situation, Kawhi Leonard and the Spurs, the future of the Blazers and the Basketball 101 program that’s part of the Professional Basketball Combine.

Basketball Insiders



Basketball Insiders publisher Steve Kyler and NBA writer David Yapkowitz talk about the future of LeBron James in Cleveland, the Paul George situation, Kawhi Leonard and the Spurs, the future of the Blazers and the Basketball 101 program that’s part of the Professional Basketball Combine.

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The Strictly Speaking Podcast


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