1) Jerry Buss and the Lakers, 1979-2013

A freshly divorced, 46-year-old billionaire playboy, Buss was the perfect avatar for ’80s Los Angeles. But just like his Lakers franchise that used obsessive work ethic to fuel their stylish pizzazz, Buss put in the effort before enjoying the spoils. Born and raised in poverty in Wyoming, he worked his way to a Ph.D. in chemistry by the age of 24 (hence, Dr. Buss), then stumbled into the real estate business that built his fortune. Buss turned Lakers games into star-studded events worthy of their Hollywood locale. Everyone from Muhammad Ali to Tom Cruise to Michael Jackson came by The Forum to be feted by Buss and gladhand his star players. He created the first NBA dance troupe, hired the first DJ in place of an organist, and was the first to turn court-side seats into a VIP experience. Behind the scenes Buss worked tirelessly to build the perfect team, both in the roster and the executives, befitting a man with a background in chemistry. The personifications were Magic Johnson, a brash, flashy star with an unrelenting competitiveness, and Pat Riley, the untested coach eager to prove his worth. Together they won five titles in the era of “Showtime,” a term coined by Buss himself, of course. When it came time to rebuild in the ’90s, Buss leaned on his general manager and confidant Jerry West, who built another dynasty around Shaquille O’Neal and Kobe Bryant. 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

Like bizarro versions of Dr. Jerry Buss, Sterling and Stepien dragged their franchises into avaricious muck. Sterling actually became the NBA’s longest tenured owner after Buss’ death, a testament more to entropy than success. A former slumlord and ambulance chaser, Sterling was an unsurprisingly miserly and racist owner. For proof go back to one of his first hires, head coach Paul Silas, whom Sterling asked to also double as team trainer to save on salary. All that stinginess and dysfunction couldn’t help but ooze onto the court and the Clippers reached the playoffs just seven times in his 30 years as owner, never past the second round. Star players came and went over the years, often either suffering career-altering injuries or otherwise ruining their reputation. One could think this “Clippers Curse” was some sort of karmic retribution, but Sterling never seemed interested in fielding a winning team anyway. In fact, like a plot out of The Producers, he would occasionally ruminate on how a losing team made him as much, if not more profit. Sterling probably could have kept that con going 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 forced Sterling to sell the team and banned him for life from league activities. As one final “fuck you” on the way out the door, Sterling initially agreed to a sale but then changed his mind and filed a frivolous lawsuit against the NBA.

Stepien’s 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, injuring several bystanders 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. Stepien lasted all of three years after purchasing the Cavaliers in 1980. Like softballs raining from the sky, he still managed to inflict maximum damage in that brief time, making some of the worst trades and free agent signings in NBA history. The most egregious decision was trading away every Cavs first round pick between 1982 and 1986, which were used on James Worthy, 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. With the win-loss record and attendance tanked, 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

There was something Jay Gatsy-esque about the nouveau riche Mark Cuban purchasing a majority stake in the Mavericks from old money Ross Perot in 2000. Cuban had no previous sports management experience but did have $285 million burning a hole in his pocket. Still only 42 years old at the time, he became the first member of Gen X to own a franchise and instantly signaled 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, often heckling the refs. He would also 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). Say what you will about his behavior but there’s no doubt Cuban’s passion was the main factor in the Mavericks renaissance of the ’00s. By adding players like Dirk Nowitzki, Steve Nash, Michael Finley, and Nick Van Exel, Cuban fielded not just a good team but an entertaining one. His loyalty and enthusiasm proved to be infectious and the Mavericks have always been fun to watch under his ownership. The results on the court speak for themselves as well, with the franchise making its first NBA Finals appearance in 2006 and winning its first title in 2011. Cuban had mellowed with age a bit by then but was still involved in all personnel decisions and still cheering on his team from the stands like an average season ticket holder. Billionaires, they’re just like us (if we owned a private Gulfstream V to fly to road games).

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. The Celtics employed the first Black player in the NBA (Chuck Cooper) and the first all-Black starting five, which included the great Bill Russell. 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 inherited by 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 Brown passed away, the Celtics retired the #1 in his honor, and the NBA followed suit by naming its championship trophy after him (later renamed after Larry O’ Brien).

6) Peter Holt and the Spurs, 1993-2016

Born and raised in San Antonio, Holt was dismayed when rumors swirled in 1993 that Spurs owner Red McCombs was willing to sell to an out-of-town buyer. Holt put together an ownership team to purchase the Spurs, keep them in San Antonio, and build not just a winning team but a full community project. He immediately established or joined forces with several community service projects, such as the Spurs Youth Basketball League and the local United Way. In turn, the community came out to support the Spurs in new record numbers. Holt inherited an already established superstar in David Robinson, then was lucky enough to add a second one in Tim Duncan. He also hired a young Gregg Popovich as general manager and the “Spurs Way” was born, the backbone of a dynasty. The Spurs won their first of five 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.