1) Jerry Buss and the Lakers, 1979-2013

Befitting of a man who made his fortune in real estate, Buss was always a gambler. He was a huge poker fan and often brought that mentality to his ownership of the Lakers. Still only 46 and freshly divorced when he purchased the franchise, he was already a notorious playboy in Hollywood and evolved into a legendary philanderer and luminary in a city already lousy with them. The Lakers’ locker room and press lounge guest lists became a who’s who of Hollywood stars in the ’80s, with everyone from Muhammad Ali to Tom Cruise to Michael Jackson swinging by to glad hand the players and be feted by Buss. He created the first NBA dance troupe, the famed Laker Girls, was the first to implement a DJ instead of an organist, and was the first to turn court side seats into a full VIP experience. He also coined the term “Showtime,” an exemplary description of the ’80s Lakers experience both on and off the court. And it all could have fallen apart before it really started. In 1981, though just one year removed from winning a title, the players were threatening open revolt against demanding coach Paul Westhead. Buss desperately tried to get general manager Jerry West to return to the bench, but West instead recommended promoting the young, untested assistant Pat Riley. Buss, as was his wont, trusted West, took a gamble on Riley, and the three worked together to create a dynasty. Chemistry was something Buss was already quite familiar with. Growing up poor and fatherless in Wyoming, he worked his way to a Ph.D. in chemistry from USC by the age of 24 (hence his Dr. Buss moniker), and took a faculty job in the university’s chemistry department before stumbling into real estate. Having worked hard all the first half of his life, he played hard as well in his second half, and the franchise followed suit, mixing a strong work ethic with an entertaining looseness, personified by its star, Magic Johnson. After winning five titles in the ’80s with Magic, Kareem Abdul-Jabbar, James Worthy, and others, Buss and West were forced to rebuild in the ’90s and eventually hit on another winning formula built around Kobe Bryant and Shaquille O’Neal that brought home five more championships. Buss passed away from cancer in 2013 at age 80, and his memorial service was a true “Showtime” event, with attendees including all kinds of luminaries and celebrities and former star players like Johnson, who honored his former owner as a “father figure.”

2) Donald Sterling and the Clippers, 1979-2014
3) Ted Stepien and the Cavaliers, 1980-1983

There’s a critical scene in the film “Slap Shot” when the movie’s protagonist, a minor league hockey player-coach played by Paul Newman, finally gets an audience with the owner of his failing team. Newman’s character pleads with the owner to sell the franchise rather than folding it, but is met with indifference from a woman who has never even attended a hockey game and just considers the franchise a glorified tax write-off. Most of us who watch the movie empathize with Newman, but if there’s anyone who sees the owner’s side of things, it’s definitely Stepien and Sterling. Both are like bizarro versions of Dr. Jerry Buss, in uniquely terrible ways. Sterling actually became the NBA’s longest tenured owner after Buss’ death, and it was Buss himself who encouraged him to move the Clippers from San Diego to Los Angeles in 1984. Having made his money first as an ambulance chaser and later as a (racist) slumlord, it’s no surprise that Sterling has always been notoriously cheap. The stories about his frugality are legion, but one of the all-time greatest is when he asked his first head coach, Paul Silas, to also double as team trainer. The avarice and selfishness in the front office couldn’t help but ooze onto the court. The Clippers made the playoffs just seven times in Sterling’s 30 years as owner, advancing past the first round just three times and never to the NBA Finals. From Marques Johnson to Bill Walton to Norm Nixon to Ron Harper to Danny Manning to Lamar Odom, the Clippers seemed to be constantly populated with star players either giving minimal effort or blowing out their knees, or both. It would be conspicuous to think that this is some sort of karma towards Sterling, but the man never seemed to care about fielding a winning team anyway, even admitting at one point that he can still make money just as easily with a loser. He probably could have kept that con ongoing indefinitely, if not for a recording released in 2014 in which he was caught on tape making racist comments. With sponsors pulling out and Clippers players threatening a boycott, the NBA league office stepped in, forcing Sterling to sell the team and banning him for life from league activities. The franchise still hasn’t found playoff success in the years since, but they have rebranded as a youthful, fun-loving group under new owner Steve Ballmar.

Whereas Sterling just seemed to be a miser, Stepien may have been certifiably insane. His first pro sports endeavor in Cleveland was a professional softball team and he once staged a promotional event where he dropped softballs from the top of the Terminal Tower, Cleveland’s tallest building. The intent was for several of his players to catch the balls, but instead he wreaked havoc on the city like a Spiderman villain, breaking one woman’s arm, injuring several others, and smashing multiple cars. It’s rare to see such an on-the-nose omen of an owner’s future relationship with his NBA team, but there it was. Stepien, a Pittsburgh native who had made his money in advertising, purchased the Cavaliers as majority owner in 1980 and lasted all of three scant years as owner and general manager. Like softballs raining from the sky, he managed to inflict damage in trades and free agent signings in those three years that would make Isiah Thomas and James Dolan blush. He started it off by signing three role players, Scott Wedman, James Edwards, and Bobby Wilkerson, to superstar-level contracts. Then, in a misguided effort to further build a veteran team that could contend immediately, he traded away every single one of the team’s first round picks between 1982 and 1986. The first pick in 1982 turned out to be the #1 overall selection, which allowed the already stacked Lakers to select James Worthy. The other picks were turned into Dennis Rodman, Derek Harper, Sam Perkins, Roy Tarpley, and Detlef Schrempf. It got so bad that the NBA had to step in and force Stepien to run all trade considerations through the league office and later implemented the “Stepien Rule” wherein a team can’t trade first round picks in consecutive years. He also burned through seven coaches in three years (including future legend Chuck Daly, who lasted just 41 games under Stepien’s regime), and his mercurial behavior led to erratic results on the floor, as players failed to find direction or inspiration. After he tanked the win-loss record and attendance, the league mercifully intervened and took the franchise away from him. (They had to actually restore several of the Cavs’ first round picks just to convince a new owner to purchase the team).

4) Mark Cuban and the Mavericks, 2000-Current

Like Jay Gatsby throwing a lavish party to outdo Tom Buchanan, it was a significant moment in 2000 when the nouveau riche Mark Cuban purchased a majority stake in the Mavericks from old money Ross Perot. A wunderkind who was a millionaire by age 32 thanks to the internet, and smart enough to cash out before the 2000 dot-com bubble crash, Cuban had no previous sports management experience but did have $285 million burning a hole in his pocket. The first of his generation to own an NBA franchise, he instantly became a new breed of owner, not just hands-on but visible. While other noted meddlers like Jerry Buss tended to stick to their luxury boxes and back offices, Cuban would sit amongst the rabble in a Mavs jersey, cheering boisterously for his team and heckling the refs, just like any other super-fan season ticket holder (who just so happens to have a private Gulfstream V to fly to road games). Though the Dallas players have always seemed to hold Cuban at arm’s length, like rich housewives with an elderly sugar daddy, his passion for the team and willingness to lavishly support it are two of the main factors in turning the franchise around. The other big factor, of course, is Dirk Nowitzki, who was in his second season when Cuban purchased the team. Behind Nowitzki, and other exciting players like Steve Nash, Michael Finley, and Nick Van Exel, the Mavericks became not only one of the league’s best teams, but one of the most exciting. Cuban’s loyalty and enthusiasm proved to be infectious, and the team always seemed to be having fun on the court, often leading the league in scoring. He would sometimes find himself outshining the team in the headlines for his criticisms of officials and the NBA league office, which would usually lead to exorbitant fines (that Cuban would always match charitably). It is notable that in 2011, when the team finally rallied behind Nowitzki and won an elusive title, Cuban was mostly quiet and unassuming throughout, matching the new workmanlike approach of his team.

5) Walter A. Brown and the Celtics, 1945-1964

He was never that big a fan of basketball, flippantly referring to it as “bounce ball” in his early ownership days. But Brown was a big fan of winning and of making money, two things he discovered were indelibly linked, and he pursued them both to every extent possible. A man used to getting his way – he inherited the Boston Garden from his father, George – and prone to throwing tantrums when he didn’t, he found a perfect conduit in team president and coach Red Auerbach in 1950. The two were determined to build a title contender by any means necessary to draw in fans, and that included crossing racial barriers. They employed the first Black player in the NBA, Chuck Cooper in 1950, and eventually the first all-Black starting five, including the great Bill Russell. As much as Brown was adamant about fielding a winner, he ignored the ailments of his Garden. Built mainly to host boxing, the arena was ill-suited for basketball, with many seats obstructed from view of the court. Eventually these faults morphed into charm, especially the close distance of the fans from the players, giving a decided home court advantage to the Celtics. Willing to experiment and think outside the box, it didn’t take long for Brown and Auerbach to hit on a winning formula, eventually winning 11 titles in 13 years between 1956 and 1969. Only six of those actually came with Brown at the helm, as he passed away in 1964 and the team was passed on to his widow, Marjorie. Though most people link the ’60s Celtics with the image of Auerbach, ever smoking a cigar and tinkering with his lineup, it all started with Brown in a back room, forever anxious and critical, but willing to entrust his failing business to Auerbach, who helped him turn it into a juggernaut. After he passed away, the Celtics retired the #1 in his honor, and the NBA followed suit by naming its championship hardware the Walter A. Brown Trophy (it was eventually changed to the Larry O’ Brien Trophy in 1984).

6) Peter Holt and the Spurs, 1993-2016

Raised in San Antonio and nearby Corpus Christi, Holt inherited a Caterpillar dealership that he eventually expanded in the nation’s largest. Like many famous successful Texans, from Conrad Hilton to George Bush to Mark Cuban, Holt employed an informal, communal, and radical atmosphere to his business proceedings. A proponent of businesses and communities working in harmony towards mutual benefits, he saw an opportunity to implement the ultimate community project when the San Antonio Spurs went up for sale in 1993. Previous owner Red McCombs was looking to unload the team quickly, despite recent success based around star center David Robinson. There were rumors the Spurs might leave Texas for a larger city with a bigger potential fan base, but the new ownership team, led by Holt, saw an opportunity to expand the fan base organically in their home city of San Antonio. Just as the city was revitalizing around its expanding famed River Walk, Holt took over the role of sole CEO in 1996 and immediately established or joined forces with several community service projects, such as the Spurs Youth Basketball League, the local United Way, and education outreach programs. The community, in turn, thankful for their own major pro sports franchise staying in town, came out to support the Spurs in new record numbers. One his first moves as owner was installing Gregg Popovich as vice president and general manager, and Popovich soon named himself as head coach. The team pulled a coup in 1998, garnering a surprise #1 overall pick in the draft lottery, allowing them to pick Tim Duncan and create the “Twin Towers” duo. Possessing two soft-spoken and collaborative superstars, the Spurs quickly improved on the court and off. They won their first of four NBA titles in 1999, but Holt may be just as proud of their winning the Pro Team Community Award in 2000, presented by the World Sports Humanitarian Hall of Fame. Now considered a standard-bearer for small market success across all the pro sports leagues, the “Spurs Way” has come to embody fiscal responsibility, teamwork, character, and community service, all in the name of their owner. He retired in 2016, ensuring a smooth transition by handing over the reigns to his wife Julianna, who was kept the franchise running smoothly even as the couple later divorced.