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.

1. 1
   Kawhi Leonard 2018-19

   Leonard won the title and Finals MVP in his only Toronto season, then declined his player option and signed with the Clippers.
   1000pts
2. 2
   Michael Jordan 1995-96

   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.
   811pts
3. 3
   Amar'e Stoudemire 2009-10

   Stoudemire opted out after the 2009-10 season with Phoenix and signed a five-year, $100 million deal with the Knicks.
   736pts
4. 4
   Juwan Howard 1995-96

   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.
   648pts
5. 5
   Gordon Hayward 2016-17

   Hayward made his first All-Star team with Utah, then opted out and signed with Boston.
   648pts
6. 6
   Brandon Ingram 2019-20

   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.
   595pts
7. 7
   Kevin Durant 2015-16

   Durant's last Oklahoma City season ended in the Western Conference finals before he signed with Golden State in free agency.
   534pts
8. 8
   Kobe Bryant 2003-04

   Bryant opted out after the 2003-04 Finals run and re-signed with the Lakers on a seven-year contract.
   463pts
9. 9
   Grant Hill 1999-2000

   Hill averaged 25.8 points in his last Detroit season before a sign-and-trade sent him to Orlando in 2000.
   463pts
10. 10
    Moses Malone 1981-82

    Malone won the 1982 MVP with Houston, then signed an offer sheet with Philadelphia that the Rockets matched before trading him to the 76ers.
    463pts
11. 11
    Ben Wallace 2005-06

    Wallace won his fourth Defensive Player of the Year award with Detroit, then signed with Chicago as a free agent.
    463pts
12. 12
    Stephen Curry 2016-17

    The final year of Curry's four-year, $44 million extension ended with a title, followed by a five-year supermax deal.
    463pts
13. 13
    Shaquille O'Neal 1995-96

    O'Neal's final season with Orlando before he became a free agent in 1996 and signed with the Lakers.
    379pts
14. 14
    Draymond Green 2014-15

    Green finished the final year of his rookie deal as a Warriors champion, then re-signed as a restricted free agent.
    379pts
15. 15
    Hassan Whiteside 2015-16

    Whiteside led the NBA in blocks for Miami, then re-signed with the Heat on a four-year, $98 million deal.
    379pts
16. 16
    Paul George 2017-18

    George declined his player option after one season in Oklahoma City and re-signed with the Thunder for four years.
    379pts
17. 17
    LeBron James 2009-10

    James won his second straight MVP with Cleveland, then announced on live television that he would join Miami as a free agent.
    379pts
18. 18
    Dwyane Wade 2009-10

    Wade opted out after the 2009-10 season and re-signed with Miami alongside two other free-agent stars.
    379pts
19. 19
    LeBron James 2017-18

    James played all 82 games and carried Cleveland to the Finals, then declined his player option and signed with the Lakers.
    379pts
20. 20
    Rashard Lewis 2006-07

    Lewis's last Seattle season preceded a six-year, $118 million sign-and-trade to Orlando in 2007.
    278pts
21. 21
    Chris Webber 2000-01

    Webber made the All-NBA first team with Sacramento, then re-signed with the Kings as a free agent in 2001.
    278pts
22. 22
    Erick Dampier 2003-04

    Dampier averaged a double-double for Golden State, then landed a seven-year deal with Dallas through a 2004 sign-and-trade.
    278pts
23. 23
    Chris Bosh 2009-10

    Bosh averaged 24 points and 10.8 rebounds in his final Toronto season before a sign-and-trade to Miami.
    278pts
24. 24
    Jimmy Butler 2014-15

    Butler turned down a contract extension before the season, won Most Improved Player, and re-signed with Chicago for five years.
    278pts
25. 25
    DeAndre Jordan 2014-15

    Jordan led the NBA in rebounding for the Clippers, agreed to join Dallas in free agency, then re-signed with Los Angeles.
    278pts
26. 26
    Kemba Walker 2018-19

    Walker made the All-NBA third team in his final Charlotte season before a sign-and-trade to Boston.
    278pts
27. 27
    Anthony Davis 2019-20

    Davis won the 2020 title with the Lakers, declined his player option and re-signed for five years.
    278pts
28. 28
    Tyrese Maxey 2023-24

    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.
    278pts
29. 29
    Tracy McGrady 1999-2000

    McGrady's breakout third season in Toronto, after which he left as a free agent for Orlando.
    0pts
30. 30
    Jalen Brunson 2021-22

    Brunson's final Dallas season included a run to the Western Conference finals before he signed with the Knicks.
    0pts

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