Playing for a winning team in the NBA isn't guaranteed. As a result, a lot of players have had more losses than wins in their careers.
Some of the top active players who have been in the league for a long time are yet to make it to the playoffs. That's because their franchises have struggled to build contending teams. The list includes the likes of Zach LaVine and De'Aaron Fox, among others. Until last season, a player of Devin Booker's caliber had also not featured in the playoffs.
It took the Phoenix Suns a long time before they built a playoff-contending team. It was worth the wait, though, as they not only qualified for the playoffs, but they also made a Finals appearance.
Nevertheless, Booker is among 18 players with over 300 NBA games to have a winning percentage under 40. On that note, here's a look at the top five on the list:
#5 Wayne Ellington - 37.3%
Wayne Ellington has been in the NBA for 12 seasons. He has earned a reputation for being one of the best long-range shooters in the league over the years. But he hasn't had much collective success in his career, though, because most of the teams he played for weren't playoff-contending ones.
He has played for the Minnesota Timberwolves, Memphis Grizzlies, Cleveland Cavaliers, Dallas Mavericks, LA Lakers, Miami Heat, Brooklyn Nets and Detroit Pistons. Ellington has made three trips to the postseason. The first was with the Mavs in 2013, the second with the Heat in 2018 and the third with the Pistons in 2019. Unfortunately, he never got past the first round with any team.
Ellington has a win percentage of over 50% with just three teams, the Grizzlies (26-14), Mavericks (22-21) and the Heat (87-77) during his career.
Throughout his 727-game career, the 33-year old has been on the winning team just 271 times. His winning percentage could improve this year, as Ellington will be playing for the championship-contending LA Lakers.
#4 Richaun Holmes - 34.4%
After a slow start to his NBA career, Richaun Holmes is quickly turning into one of the most impactful big men in the league. The 37th pick in the 2015 draft started his stint in the NBA with the Philadelphia 76ers. But the Sixers were far from the perennial playoff contenders back then.
Holmes recorded just seven wins in his rookie season out of the 51 games he played, and 16 wins in his sophomore year. His best campaign with the team was during the 2018-19 campaign, when he won 30 of 48 games. He was injured towards the end of the regular season, but returned to make his NBA playoffs debut.
It remains the only playoff appearance of his career to date. Holmes has played for the Phoenix Suns and the Sacramento Kings since then. Both were lottery teams when he played for them. His NBA win-loss record in that stretch is 61-114. Overall, Holmes' win/loss record stands at 114-217.