# The 30 Greatest Contract-Year Seasons in NBA History

> Some of these players cashed in, a few walked out on a franchise, and one or two turned a single big year into a deal fans still bring up.

*By YPB Team · Published November 9, 2026 · https://youpick.best/ranking/the-30-greatest-contract-year-seasons-in-nba-history*

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## Current results (no votes yet)

1. **Kawhi Leonard 2018-19** — score 1000/1000
   Leonard won the title and Finals MVP in his only Toronto season, then declined his player option and signed with the Clippers.
2. **Michael Jordan 1995-96** — score 811/1000
   The last season of Jordan's 1988 contract, in which the Bulls went 72-10 and he won MVP and Finals MVP before signing a one-year deal.
3. **Amar'e Stoudemire 2009-10** — score 736/1000
   Stoudemire opted out after the 2009-10 season with Phoenix and signed a five-year, $100 million deal with the Knicks.
4. **Juwan Howard 1995-96** — score 648/1000
   Howard made the All-Star team with Washington, then became a free agent and re-signed with the Bullets after his Miami deal was voided.
5. **Gordon Hayward 2016-17** — score 648/1000
   Hayward made his first All-Star team with Utah, then opted out and signed with Boston.
6. **Brandon Ingram 2019-20** — score 595/1000
   Ingram made the All-Star team and won Most Improved Player in the last year of his rookie deal, then re-signed with New Orleans.
7. **Kevin Durant 2015-16** — score 534/1000
   Durant's last Oklahoma City season ended in the Western Conference finals before he signed with Golden State in free agency.
8. **Kobe Bryant 2003-04** — score 463/1000
   Bryant opted out after the 2003-04 Finals run and re-signed with the Lakers on a seven-year contract.
9. **Grant Hill 1999-2000** — score 463/1000
   Hill averaged 25.8 points in his last Detroit season before a sign-and-trade sent him to Orlando in 2000.
10. **Moses Malone 1981-82** — score 463/1000
   Malone won the 1982 MVP with Houston, then signed an offer sheet with Philadelphia that the Rockets matched before trading him to the 76ers.
11. **Ben Wallace 2005-06** — score 463/1000
   Wallace won his fourth Defensive Player of the Year award with Detroit, then signed with Chicago as a free agent.
12. **Stephen Curry 2016-17** — score 463/1000
   The final year of Curry's four-year, $44 million extension ended with a title, followed by a five-year supermax deal.
13. **Shaquille O'Neal 1995-96** — score 379/1000
   O'Neal's final season with Orlando before he became a free agent in 1996 and signed with the Lakers.
14. **Draymond Green 2014-15** — score 379/1000
   Green finished the final year of his rookie deal as a Warriors champion, then re-signed as a restricted free agent.
15. **Hassan Whiteside 2015-16** — score 379/1000
   Whiteside led the NBA in blocks for Miami, then re-signed with the Heat on a four-year, $98 million deal.
16. **Paul George 2017-18** — score 379/1000
   George declined his player option after one season in Oklahoma City and re-signed with the Thunder for four years.
17. **LeBron James 2009-10** — score 379/1000
   James won his second straight MVP with Cleveland, then announced on live television that he would join Miami as a free agent.
18. **Dwyane Wade 2009-10** — score 379/1000
   Wade opted out after the 2009-10 season and re-signed with Miami alongside two other free-agent stars.
19. **LeBron James 2017-18** — score 379/1000
   James played all 82 games and carried Cleveland to the Finals, then declined his player option and signed with the Lakers.
20. **Rashard Lewis 2006-07** — score 278/1000
   Lewis's last Seattle season preceded a six-year, $118 million sign-and-trade to Orlando in 2007.
21. **Chris Webber 2000-01** — score 278/1000
   Webber made the All-NBA first team with Sacramento, then re-signed with the Kings as a free agent in 2001.
22. **Erick Dampier 2003-04** — score 278/1000
   Dampier averaged a double-double for Golden State, then landed a seven-year deal with Dallas through a 2004 sign-and-trade.
23. **Chris Bosh 2009-10** — score 278/1000
   Bosh averaged 24 points and 10.8 rebounds in his final Toronto season before a sign-and-trade to Miami.
24. **Jimmy Butler 2014-15** — score 278/1000
   Butler turned down a contract extension before the season, won Most Improved Player, and re-signed with Chicago for five years.
25. **DeAndre Jordan 2014-15** — score 278/1000
   Jordan led the NBA in rebounding for the Clippers, agreed to join Dallas in free agency, then re-signed with Los Angeles.
26. **Kemba Walker 2018-19** — score 278/1000
   Walker made the All-NBA third team in his final Charlotte season before a sign-and-trade to Boston.
27. **Anthony Davis 2019-20** — score 278/1000
   Davis won the 2020 title with the Lakers, declined his player option and re-signed for five years.
28. **Tyrese Maxey 2023-24** — score 278/1000
   Maxey made his first All-Star team and won Most Improved Player in the last year of his rookie deal, then re-signed with Philadelphia.
29. **Tracy McGrady 1999-2000** — score 0/1000
   McGrady's breakout third season in Toronto, after which he left as a free agent for Orlando.
30. **Jalen Brunson 2021-22** — score 0/1000
   Brunson's final Dallas season included a run to the Western Conference finals before he signed with the Knicks.

Tags: sports, basketball, nba, seasons, free agency, contracts