Success can be defined in many ways and on this list because someone has won 1 or multiple "Coach of the Year" awards or Championships does not signify they had a successful career. Some coaches are brilliant masterminds while others are a pauper, and the best of the best didn't just know when to sub in the right players and create a good system, but also brought out the best in every single one on the roster and creating great chemistry.
Criterium: 800 games minimum and coached multiple superstars
Check the list of the Top 9 Best and Bad Coaches.
9th Bad: Dick Motta (1968-87, 1990-91, 1994-97)
1952 Games / 935 Wins / 1017 Losses / 2X Conference Championships / Coach of the Year (1971) / NBA Championship (1978)
Ever heard the phrase "It ain't over 'till the fat lady sings"? He brought it to life after a game 7 victory in the Finals. Motta wasn't a horrid coach, by his acclimates he just couldn't remain consistent and had some strings of misfortune. Out of his 25 seasons coaching, 13 of those were losing seasons and has the 4th most losses by a coach.
9th Best: George Karl (1984-88, 1992-03, 2005-13, 2015-16)
1999 Games / 1175 Wins 824 Losses / 1X Conference Champion / Coach of the Year (2013)
He had the golden touch and 22/27 seasons coaching were winning seasons. After a coaching stint in the CBA, he joined the NBA and coached the Cavs in '84 and helped them reach the Playoffs his first year, but was dismissed the following year after a disappointing record and became a scout for the Bucks. In '86 he became the coach for the Warriors and took them to the Playoffs for the first time in 10 years, he quit after the Warriors traded away his best players without advising him and went back to the CBA where he coached the Patroons and led them to a 50-6 record.
In '92 he took the coaching job for the Sonics and led them to the Playoffs 7 years in a row, moved back with the Bucks as coach and GM, rebuilt that organization and led them to 3 straight Playoffs. We all know about his beef with Sacramento and Boogie, but just prior to that he made Denver a contender with a younger Melo while leading them to a franchise best record.
8th Bad: Bill Fitch (1970-92, 1994-98)
2050 Games / 944 Wins / 1106 Losses / 2X Conference Champion / 2X Coach of the Year (1976,1980) / 1 Championship
With so many accomplishments it's hard to put him among the worst, but from his 27 seasons coaching he spent 14 of those with a losing record. Although he is among the top 10 in wins he is 2nd in losses and it's largely in part to taking the job with the Nets and Clippers of the 90's. Those franchises were unsolvable and he just couldn't or didn't know how to help the disastrous situations.
8th Best: Don Nelson (1976-2010)
2398 Games / 1335 Wins / 1063 Losses / 3X Coach of the Year (1983, 1985, 1992)
The All-Time wins coach spent 23/31 seasons with a winning record and is credited for creating great strategies that include "Nellieball" which was the Point Forward position and "Hack-a-Shaq". Even though Kareem left to LA, he took over the Bucks organization in 1976 and was able to win 14 more games without Kareem and led the Bucks to 7 straight Central Division titles. In 1997 he was named a head coach for the Mavs and his brilliance once again showed when he traded, on draft day, his picks to Milwaukee and Phoenix and used those picks to draft Nowitzki and Nash.
While with the Mavs he insisted Mark Cuban to match the max contract offer from Suns for Steve Nash, we all know how that turned out. He stepped down from the Mavs and moved on to the Warriors in 2006 where in his first season he lead the 8th seeded Warriors to upset the NBA's best record and Ex-team Mavs.
7th Bad: Gene Shue (1967-1989)
1645 Games / 784 Wins / 861 Losses / 2X Conference Champion / 2X Coach of the Year (1969, 1982)
His 861 losses are the 6th most in NBA history. With 22 seasons under his belt 13 of those were a losing season.
7th Best: Jerry Sloan (1979-82, 1988-11)
2024 Games / 1221 Wins / 803 Losses / 2X Conference
23/26 seasons coaching were a winning record and his tenure in Utah was a great success. Went 16 consecutive years to the Playoffs, Accumulated 6 Division Championships and is 1 of 3 coaches to have 10 consecutive 50+ win seasons largely in part to having John Stockton and Karl Malone on the roster. Inducted into the Hall of Fame and has the 3rd most wins in coaching history.
6th Bad: Mike Dunleavy (1990-96, 97-01, 2003-10)
1329 Games / 613 Wins / 716 Losses / 1 Conference Championship / Coach of the Year (1999)
No easier way to begin a coaching career than with the Lakers led by Magic and Vlade. The first season in lost to Jordan and Bulls in the Finals 4 games to 1. 2nd season with Lakers lost in first round and decided to go to Milwaukee where he was mediocre at best. Joined the Trailblazers and was fired after 4 seasons, moved to the Clippers did a decent job, but ultimately was fired and accused of defrauding the team. In total 10/17 were losing seasons.
6th Best: Lenny Wilkens (1970-2005)
2487 Games / 1332 Wins / 1155 Losses / 2X Conference Champion / 2X Gold Medal (1992, 1996) / Coach of the Year (1993) / 1 Championship with Seattle SuperSonics (1978-79)
Pretty solid as a Player and pretty solid as a Coach, he is currently 2nd for most wins by a Coach. He is a 3X inductee into the Hall of Fame, 1st as a Player, 2nd as a Coach, 3rd as an Assistant Coach for which he was with the '92 Dream Team. Even with all his accomplishments he has the most losses in history and had 10 losing seasons
5th Bad: Alvin Gentry (1995-2017)
869 Games / 399 Wins / 470 Losses
10/14 seasons, you guessed it, losing season and most of his coaching tenures have been as interim. He had success with Phoenix, leading them to the Conference Finals in 2009, but decided an assistant coaching job with the Clippers would be more suiting. He later jumped ship as an assistant coaching for the Warriors in 2015 and practically walked into a Championship. Shortly after and currently signed with the Pelicans, he couldn't figure out the Duo of Cousins and Davis where he is expected to be fired for a 4th time.
5th Best Chuck Daly (1981-94, 1997-99)
1075 Games / 638 Wins / 437 Losses / 3X Conference Champion / Gold Medal (1992) / 2X NBA Championships (1989, 1990)
Even he was able to salvage the pre Jason Kidd-Nets and post Shaq-Magic of the 90's and his only losing season came with the Cavs. When the Pistons hired him Detroit never had a consecutive winning season, but as soon as Daly arrived they never missed the Playoffs. He was the man behind the Dream Team, granted anybody could coach the greatest assembly of players ever, it took a special mind to condition them and work together in a new system.
4th Bad: Kevin Loughery (1973-1995)
1136 Games / 474 Wins / 662 Losses
He had tendency to take over teams midway through season and do little to no change. He spent 12/17 seasons, you guessed it, losing and 5 of those were as interim head coach and his best season was a 43 win year.
4th Best: Red Auerbach (1947-1966)
1417 Games / 938 Wins / 479 Losses / Coach of the Year(1965) / 9X Champion (1957, 1959-66)
As an NBA entity he has a total of 16 Championships in the span of 29 years when he became an Executive following his coaching career. Is in fact 2nd with most Championships by a head coach and it all came with the Celtics, entirely because of Bill Russell. He introduced the fast pace offense and Fast Break to the NBA, but most importantly Red broke multiple color barriers by drafting the first African-American into the NBA in 1950 (Chuck Cooper) had the first African-American starting 5 and hired the first African American head coach in 1966 (Bill Russell).
He would light a cigar when he felt his team was about to win and in total of 20 years as coach he only had 1 losing season.
3rd Bad: Byron Scott (2001-2016)
1101 Games / 454 Wins / 647 Losses 11 losing seasons / 2X Conference Champion / Coach of the Year (2008)
He was a great player and team mate, but far from that once he became a head coach. Multiple times have player openly admitted to having wanted Scott out of his coaching position for lack of knowledge and chemistry. He coached the post LeBron Cavs to a worst season in franchise history including a 26 losing streak. Following Cleveland he went on to coach the Lakers and lead that tank to a Franchise worse 17-65 record capping the 5th consecutive time he has coached a team to last place within their division.
3rd Best: Pat Riley (1981-90, 1991-03, 2005-08)
1904 Games / 1210 Wins / 694 Losses / 4X Conference Champion / 3X Coach of the Year (1990, 1993, 1997) 5X NBA Champion
He coached the best team of the 80's and missed the Finals only twice during his 9 year tenure with the Lakers. Coach of the Year with 3 separate teams, he is the 4th most winning coach and in his 24 seasons coaching he only had 3 losing seasons with 7 60+ Win seasons.
2nd Bad: Mike Brown (2006-2014)
563 Games / 347 Wins / 216 Losses / 2 60+ Win seasons / 1 Eastern Conference Championship / Coach of the Year 2009
Coaching is not Mike Brown's niche. He was unable to reach the finals while having the best record and a Prime, high intensity performing LeBron in roster. Eventually fired by the Cavs, was quickly hired to succeed Phil Jackson in LA. When he received a star studded lineup that included Kobe Bryant, Dwight Howard, Ron Artest, Pau Gasol and you start 0-8 it's no mystery why they would fire him. Maybe he would've figured out a system that could work, but what is certain, that Princeton system was dumb. He couldn't win with that roster, but he was not as awful as his successor.
2nd Best: Phil Jackson (1990-2011)
1640 Games / 1155 Wins / 485 Losses / 0 Losing seasons / 6 60+ win seasons / 1 72 win season / 13X Conference Champion / 11X NBA Champion
When you have the greatest player to ever play the game in MJ, an established roster with playoff experience you're practically walking into a winning situation. But it takes more than just experience to win and Phil brought even more out of Jordan elevating his game creating 2 3-Peats. He moved on to an even better situation with the best Center of the era, a young Kobe Bryant and an even better roster, where if not for Phil that team would have never won 3 in a row because Phil kept the team focused on winning and not on the Drama ensuing.
His coaching abilities were proven when he had Kobe and a solid Lakers team going against teams with a deep star studded roster that included the Celtics and Magic and managed to edge out 2 more championships out of 3 tries.
1st Bad: Mike D'Antoni (1999-2017)
963 Games / 510 Wins / 453 Losses
Granted he is under 1,000 games, Mike had possibly the best Pick 'n Roll duo ever in a young Stoudemire and Nash with a deep Suns team best known for their league changing fast pace, and the best he did was conference finals? He was a mistake hire by the Lakers and before Kobe got injured in the end of the 2013 season, he didn't know how to pair Kobe, Dwight and Pau and just inched into the Playoffs only to get swept? Lead a younger more productive Melo and a still dominant Stoudemire with a solid New York team to a 42-40 record to also get swept in the 1st round. Although he wasn't swept this year he has been eliminated of the 2017 Playoffs.
1st Best: Gregg Popovich (1997-2017)
1656 games / 1150 Wins / 506 Losses / 6X Conference Champion / 3X Coach of teh Year (2003, 2012, 2014) / 5X NBA Champion
When Popovich replaced Bob Hill 18 games in the '96 season, no one expected him to keep his job after finishing with a 17-47 record much less envision winning multiple Championships. The only proven talent on roster was David Robinson so when they drafted Duncan, he was unproven, but Pop brought out the best in him and immediately turned the franchise around.
Adding player like Manu, Parker, Aldridge, Kawhi, helped him and the Spurs remain contenders up to this date. Popovich had a knack for playing the right people and elevating their game while adding consistency. In his 21 year career he's only had 1 losing season while massing 6-60+ Win seasons.