Since 1983 (i.e. the last 32 years), eight players account for all but three of the championships. Jordan, Kobe, Shaq, LeBron, Hakeem, Duncan, Magic, Bird, Isaiah. The outliers are the '11 Mavs, '08 Celts, '04 Pistons.
Superstar players who break through to win one tend to win multiples (Dirk being the exception). Part of it is because they are great players, but surely the playoff experience plays a part.
For example, there are several years where an upstart team had the best record in the league, only to be beaten in the playoffs by a more experienced team:
| Year | Team | Record | Result | Lost to? |
|---|---|---|---|---|
| 90-91 | Portland Trailblazers | 63-19 | Lost West Finals | Pistons |
| 91-92 | Chicago Bulls | 67-15 | Won NBA Title | Bulls |
| 92-93 | Phoenix Suns | 62-20 | Lost NBA Finals | Bulls |
| 93-94 | Seattle Sonics | 63-19 | Lost First round | Rockets |
| 94-95 | San Antonio Spurs | 62-20 | Lost West Finals | Rockets |
| 95-96 | Chicago Bulls | 72-10 | Won NBA Title | Bulls |
| 96-97 | Chicago Bulls | 69-13 | Won NBA Title | Bulls |
| 97-98 | Utah Jazz | 62-20 | Lost NBA Title | Bulls |
| 98-99 | San Antonio Spurs | 37-13 | Won NBA Title | Spurs |
| 99-00 | Los Angeles Lakers | 67-15 | Won NBA Title | Lakers |
| 00-01 | San Antonio Spurs | 58-24 | Lost Semi-Finals | Lakers |
| 01-02 | Sacramento Kings | 61-21 | Lost West Finals | Lakers |
| 02-03 | Dallas Mavericks | 60-22 | Lost West Finals | Spurs |
| 03-04 | Indiana Pacers | 61-21 | Lost East Finals | Pistons |
| 04-05 | Phoenix Suns | 62-20 | Lost West Finals | Spurs |
| 05-06 | Detroit Pistons | 64-18 | Lost East Finals | Heat |
| 06-07 | Dallas Mavericks | 67-15 | Lost First Round | Spurs |
| 07-08 | Boston Celtics | 66-16 | Won NBA Title | Celtics |
| 08-09 | Cleveland Cavaliers | 66-16 | Lost East Finals | Lakers |
| 09-10 | Cleveland Cavaliers | 61-21 | Lost Semi-Finals | Lakers |
| 10-11 | Chicago Bulls | 62-20 | Lost East Finals | Mavs |
| 11-12 | Chicago Bulls | 50-16 | Lost First Round | Heat |
| 11-12 | San Antonio Spurs | 50-16 | Lost West Finals | Heat |
| 12-13 | Miami Heat | 66-16 | Won NBA Title | Heat |
| 13-14 | San Antonio Spurs | 62-20 | Won NBA Title | Spurs |
The '91 Trailblazers, '93 Suns, '95 Spurs, '98 Jazz, '02 Kings, '03 Mavericks, '05 Suns, '06 Pistons, '10 Cavs were the best regular season teams but lost to teams with playoff/finals experience. Several others just lost to random teams in the playoffs. The teams that end up winning, consistently, are the ones that have been there before.
So my point is: having experience seems to matter. Maybe it's not "playoff" experience necessarily, but maybe it's just about how to manage an entire season in order to optimize performance in the playoffs.