1) Michael Jordan, Bulls (’87-’88)

Of his five league MVP seasons, Jordan subsequently led the Bulls to the championship in four of them (in 1991, 1992, 1996, and 1998). That places him second all-time behind Bill Russell (who did it five times) for the most seasons earning MVP and a championship but Jordan’s first MVP season ended in disappointment. The award was certainly deserved in ’87-’88, as he won his second straight scoring title, led the NBA in steals per game, earned Defensive Player of the Year for the first time, and carried the Bulls to 50 wins and the #3 seed in the East. His postseason started strong, with two 50-point performances in a first round series victory over the Cavaliers but Jordan ran into his kryptonite in the Conference Semifinals, struggling against the Pistons as the Bulls were eliminated in five games. He eventually got his revenge in ’90-’91, defeating Detroit in the Conference Finals en route to earning both league MVP and Finals MVP for the first of four times in his career.

2) Wes Unseld, Bullets (’68-’69)

Only two players in NBA history have earned MVP in their rookie season. Wilt Chamberlain was the first in ’59-’60 and he led his Warriors to the Conference Finals that year, where they put up a fight against the dynastic Celtics. Unseld was the second in ’68-’69 and his subsequent postseason was much briefer. His (then Baltimore) Bullets entered the playoffs as the top seed in the East, an incredible accomplishment considering they had finished 36-46 the year prior and a testament to Unseld’s talent spurring a turnaround. Waiting in the first round was the soon-to-be-familiar Knicks, who ultimately eliminated Unseld and the Bullets in five of the next seasons. It didn’t help that Baltimore was beat up, with several players nursing injuries and All-Star Gus Johnson sidelined completely with a knee issue. Unseld averaged 18.8 points and 18.5 rebounds per game but was outclassed by veteran Willis Reed as New York advanced in a sweep. A fellow star rookie and future teammate Elvin Hayes also led a remarkable turnaround of his Rockets in ’68-’69 only to be quietly eliminated in the first round.

3) LeBron James, Cavaliers (’09-’10)

With championship-or-bust expectations and free agency looming, all eyes were on James in the spring of 2010. His Cavaliers had won 60+ games and clinched the #1 seed in the East for the second straight season, advanced past a feisty Bulls team in the Conference Quarterfinals, and opened up a 1-0 series lead against the Celtics in round two. Things started to fall apart on May 3, the day after it was announced that James had been named MVP for the second year in a row. Cleveland was blown out that night in game two at home by a Celtics team most had written off multiple times during the ’09-’10 season. The Cavaliers came back to win game three in Boston but were swept the rest of the way and defeated in six. Cleveland fans likely get PTSD recalling the image of James pulling off his jersey in frustration while exiting the court after game six, as his teammates failed to back him up offensively. Just a couple months later, he was live on television announcing his departure from Cleveland to sign with the Heat.

4) Moses Malone, Rockets (’78-’79)
5) Moses Malone, Rockets (’81-’82)

’77-’78 was a disastrous season for the Rockets, who lost their young star center, Malone, to a stress fracture in his foot and their team captain, Rudy Tomjanovich, to facial and spinal injuries after he was punched by Kermit Washington. They turned things around in ’78-’79, with Malone becoming the first league MVP in franchise history and leading the team back to the postseason. But despite being the higher seed in their first round series against the Hawks, they were swept, 2-0 (this was one of the final seasons the NBA utilized a best-of-three format in the first round). They would eventually make a surprise run to the NBA Finals in 1981 with Malone leading the way, but when the superstar center won his second league MVP award in ’81-’82, the resulting postseason was again disappointing. This time, they were the lower seed in the first round and were eliminated by the SuperSonics. These would turn out to be Malone’s final games with Houston, as he was traded that summer to the 76ers and in ’82-’83 wound up winning both league MVP and Finals MVP. As it stands, he’s one of four players, along with Dirk Nowitzki, Wes Unseld, and Russell Westbrook, to be eliminated in the first round of the playoffs the same season he was named MVP.

6) Dirk Nowitzki, Mavericks (’06-’07)

Only 33 players have been named MVP in NBA history and for most of them, accepting that trophy was a pinnacle of their career. This wasn’t the case for Nowitzki in 2007, who was seemingly more embarrassed than anything else. His Mavericks had entered the playoffs with 67 wins and the #1 overall seed only to lose in shocking fashion in the first round to the “We Believe” Warriors. In fact, the German superstar was reportedly nursing a hangover from drinking away his sorrows when he learned that the NBA was going to honor him with its top award. In the years prior to 2007, the NBA had made a habit of handing out the MVP trophy before a second round playoff game but Nowitzki had become the first MVP winner since Moses Malone in 1982 to get eliminated in the first round. This forced the league to award it during a press conference to a suit-clad, bashful-looking Nowitzki. The proceedings were a lot more joyous four years later, when Nowitzki accepted the Finals MVP trophy after leading the Mavericks to the ’10-’11 championship.

7) Karl Malone, Jazz (’98-’99)

It’s already one of the most controversial MVP votes in NBA history and Malone certainly didn’t help his case for legitimacy in the 1999 playoffs. The 35-year-old power forward was his typically, consistently terrific self during the strike-shortened ’98-’99 season but struggled in the playoffs. Utah was seeking a third consecutive Western Conference title but barely survived a dogfight with the young, upstart Kings in the first round before getting summarily dominated by the Trail Blazers in the Conference Semifinals. Malone had some decent moments in that series but also often looked old and tired, especially in the clinching game six, where he shot 3-of-16 from the field and finished with just eight points. In an interesting twist, the player who finished second in MVP voting behind Malone, Alonzo Mourning, had an even more disastrous postseason, as his top seeded Heat averaged less than 80 points per game and were upset in the first round by the Knicks. Meanwhile, the MVP voting third place finisher, Tim Duncan, earned Finals MVP honors as he led the Spurs to the championship.

“Amidst constant rumors and innuendo about his impending free agency decision, Antetokounmpo also had to deal with COVID protocols and isolation, an ejection and suspension for head butting Washington’s Moe Wagner during a game, and his team wildcat striking a game in protest after a police shooting occurred near Milwaukee.”

8) Bill Walton, Trail Blazers (’77-’78)

As is usually the case with Walton, this is a bit of a tragic entry on our list. Coming off a career making performance in the 1977 playoffs, when he earned Finals MVP while lead the Blazers to the championship, the star center had an incredible but ultimately unfulfilling follow-up in ’77-’78. Despite missing 24 games with a broken foot that would dog him for the remainder of his career, Walton was named league MVP. Part of that was his dominant performance when healthy and part of it was the paucity of talent in the NBA in the late ’70s (it helped that Kareem Abdul-Jabbar also missed significant time due to injury). After his teammates, especially Maurice Lucas, were able to hold on to the #1 seed in the West during his two months sidelined, Walton returned for their Conference Semifinals series against the SuperSonics. He arguably came back too soon (this became a major controversy, ending in Walton suing the Portland team doctor), as he re-aggravated the injury in game two. As they did during the regular season, Lucas and the Blazers fought valiantly without their star center but were ultimately eliminated by Seattle in six games. Walton would never suit up for the Blazers again, demanding a trade that summer and receiving it to the Clippers.

9) Russell Westbrook, Thunder (’16-’17)

With James Harden having been traded to the Rockets years earlier and Kevin Durant fleeing as a free agent for Golden State, Westbrook took on a bigger responsibility in the Thunder offense in ’16-’17 and made history in the process. He became just the second NBA player ever, after Oscar Robertson, to average a triple-double over the course of a season, doing so while winning the scoring title with 31.6 points per game. It was a Herculean individual effort and the Thunder needed all of it, as the otherwise so-so roster barely qualified for the playoffs as the #6 seed in the West, setting up a Conference Quarterfinals battle against former teammate Harden and Houston. While Westbrook was incredible, especially in game two when he finished with 51 points, 13 assists, and 10 rebounds, Harden was equally great and had the far superior supporting cast, who finished off the series in five games. Unlike Dirk Nowitzki, who had suffered a similar fate in 2007, Westbrook got to accept his MVP trophy in a more dignified manner, as this was the first year the NBA instituted its post-Finals “Awards Ceremony” event, which has since been discontinued due to COVID restrictions.

10) Artis Gilmore, Kentucky Colonels (’71-’72)
11) Julius Erving, New York Nets (’74-’75)

Despite the league’s often tumultuous nature, the ABA actually had most of its league MVP winners go on to postseason success. It started with Connie Hawkins in ’67-’68, who was named MVP and soon after Finals MVP after leading the Pittsburgh Pipers to the championship. In fact, Gilmore in ’71-’72 snapped a streak of the first four ABA MVPs subsequently leading their team to at least the Conference Finals. An impossibly strong center with a sweet, short shooting touch, Gilmore was a perfect fit on the Kentucky Colonels and earned MVP as a rookie while leading them to a league record 68 wins in ’71-’72. But the high-scoring Colonels went ice cold in the first round of the playoffs and were stunned in six games by the Nets, who were led at the time by Rick Barry. Kentucky got some measure of revenge three years later, when Nets superstar Erving earned his second consecutive MVP and led the team to a tie with the Colonels for first place in the East. Gilmore led Kentucky to victory in a one-game tiebreaker to earn the #1 seed, which catapulted them to eventually winning the only championship in franchise history, with Gilmore earning Finals MVP honors. Things went less successfully for Erving and the Nets, who were upset in the first round by the Spirits of St. Louis.

12) Tim Duncan, Spurs (’01-’02)

It’s difficult to overstate just how stacked the Western Conference was in the early ’00s. In addition to the Lakers and Spurs dynasties that would come to define the decade, you also had consistent title contenders with killer rosters in Dallas, Portland, Minnesota, and Sacramento. Teams with 50 regular season wins would regularly become first round fodder and the ’01-’02 Spurs narrowly avoided that fate. Duncan earned his first MVP award that season after finishing in the top five in voting each of the prior four years. He averaged career highs in points, rebounds, assists, and blocks while leading the Spurs to a 58-24 record. They survived an upset attempt from Gary Payton and the SuperSonics in the first round, just holding off the #7 seed in five games (in a best-of-five) to set up a showdown with the two-time defending champion Lakers in the Conference Semifinals. San Antonio held the lead going into the fourth quarter in every game in the series but somehow managed to win just one out of five. 19-year-old rookie Tony Parker especially struggled against L.A. but would redeem himself a year later in the postseason when Duncan earned both league MVP and Finals MVP in ’02-’03.

13) Magic Johnson, Lakers (’89-’90)

In his first season playing without Kareem Abdul-Jabbar, Johnson was incredible as always in ’89-’90. He averaged 20+ points, 10+ rebounds, and six-plus assists per game for the third time in his career and, as it had the previous two times, it ended with him earning league MVP. Even more impressive was that he led the Lakers to the best record in the NBA with 63 wins despite the team being in somewhat of a rebuild, with other stalwarts like Michael Cooper and Mychal Thompson starting to slip. Just as they had dominated the Western Conference in the ’80s, the Lakers seemed primed to start off the ’90s on a similar tear until they ran into a young and hungry Suns team in the Conference Semifinals. Avenging a sweep at the hands of Los Angeles in the prior year’s Conference Finals, Phoenix was dominant in the re-match, putting away the series in five games. Though Johnson was unstoppable offensively, averaging 30.2 points and 12.2 assists per game, he could not stop the Suns’ speedy young point guard Kevin Johnson, who keyed the upset. It broke a streak of eight consecutive seasons that the Lakers had reached at least the Conference Finals and though they managed to return to the NBA Finals in 1991, it really portended the end of the “Showtime” era.

14) Giannis Antetokounmpo, Bucks (’19-’20)

Perhaps the only MVP awarding that can rival Dirk Nowitzki’s in 2007 in terms of awkwardness was Antetokounmpo in 2020. By the time he was announced as MVP for the second straight season, the Greek superstar was back home in Athens, as his Bucks had been unceremoniously eliminated by the Heat over a week earlier. He accepted the award via video conferencing in a contrite manner, noting that it was nothing compared to a potential championship. It was an arguably appropriate ending to an uncanny season for Antetokounmpo. Milwaukee was looking near unstoppable when the league shut down operations in March of 2020 but struggled to recapture the magic when play resumed on the Disney World campus a few months later. Amidst constant rumors and innuendo about his impending free agency decision, Antetokounmpo also had to deal with COVID protocols and isolation, an ejection and suspension for head butting Washington’s Moe Wagner during a game, and his team wildcat striking a game in protest after a police shooting occurred near Milwaukee. It all crested in an especially frustrating Conference Semifinals loss to the Heat, where Giannis committed a costly foul in the waning moments of game two, then was forced to sit out the clinching game five with an ankle injury.