The Greatest Modern Dynasties Bracket Challenge – Part I

by David Arkow

Sports fans are obsessed with deciding who is the best and crowning champions. In the spirit of the NCAA Tournament, we have set up the “Dynasty Bracket Challenge” to complement our unveiling of the greatest dynasties ever. To select the teams for the bracket, we chose the best dynasties in each sport in each decade over the past 50 years. This provides interesting matchups across eras to compare teams which wouldn’t normally be analyzed together. Since three years is too short to be considered a dynasty, and 10 and 15-year time intervals can’t always capture a dynasty’s true peak, we’ve chosen to define our dynasties over five-year intervals. This format will exclude some worthy teams, such as pre-1970s dynasties (1950s Yankees), teams that relied more on longevity than peak performance (2000s Spurs), or teams that played in the shadow of an even more dominant dynasty (1980s Celtics). However, these restrictions will ensure that the final teams are the most dominant and were able to succeed despite obstacles such as salary caps, increased competition, longer postseasons, and free agency.


To be considered a dynasty, teams need to have sustained excellence in both the regular season and the playoffs. Therefore, we calculated each team’s performance during the regular season (as measured by Z-scores of winning percentage) and during the playoffs (as measured by “dynasty points,” with more points being awarded for advancing further in the playoffs). Then, we set each team’s score on a 0-100 scale and added up the regular season and postseason scores to get the dynasty’s overall score. To learn more about the details of our methodology, please read our overview article.

As in March Madness, this dynasty bracket will be split into four “regions” based on sport, and there will be a play-in game between the bottom two teams in each sport. This results in 20 total teams with representatives from the four major North American sports (NBA, NHL, NFL, and MLB) across five decades. The winner of each sport region will advance to the Final Four, where the best dynasty of all-time will be decided.


No bracket is interesting without any upsets. Our rankings are great at using data to figure out the best dynasties, but they don’t always account for intangibles like memorable narratives or star players. The 1990s Detroit Red Wings might rate slightly higher than Michael Jordan’s Chicago Bulls in our dynasty rankings, but casual fans likely remember the Jordan’s dominance more. This bracket will not simply advance the higher seed (as per our dynasty rankings), but will look into the story behind the numbers to determine the greatest sports dynasties of the past 50 years. We recognize that there is no one right answer and hope that this will encourage further debate and discussion about the best dynasties of all time, now with some evidence to back it up.

Honorable Mentions

These NBA and MLB teams were great. However, they were overshadowed by another even better dynasty playing at the same time, so they did not make the tournament.

1983-1987 Boston Celtics
1995-1999 Atlanta Braves
1971-1975 Oakland A’s
2002-2006 San Antonio Spurs
2009-2013 Miami Heat

NBA Region

Play-In Game: 1988-1992 Chicago Bulls (#12) vs. 1971-1975 Boston Celtics (#15)

Despite finishing first in the Eastern Conference all five years and having four Hall of Fame players in John Havlicek, Dave Cowens, Jo Jo White, and Paul Westphal, the Boston Celtics fall to the first Jordan Bulls three-peat. Some fans will wonder what distinguishes the first Bulls three-peat from the second (1995-98). The difference is prime Michael Jordan. From 1988-1992, Jordan turned in five of his seven best single season performances (which all rank in the Top 10 seasons of all-time) according to FiveThirtyEight’s RAPTOR WAR. Only one season (1996) from the second three-peat makes that list. Interestingly enough, the second three-peat Bulls ranks higher on our three-year dynasty list than the first three-peat Bulls, due to their greater regular season dominance. But since this bracket is for five year dynasties, the 1995-98 Bulls didn’t make the cut because they were segmented by Jordan’s first retirement and MLB stint (1994) and then his second retirement (1999).

Semifinal #1: 2014-2018 Golden State Warriors (#1) vs. 1988-1992 Chicago Bulls (#12)

Both of these dynasties won three championships, but what separates the Warriors is their regular season domination. Over their respective five year spans, the Bulls were 287-123 (.700), while the Warriors were 322-98 (.766). Both are extremely impressive, but these Warriors boast the highest regular season score of all five year dynasties across all sports. The 2015-2016 Warriors also had a higher peak, breaking the record for most regular season wins (73) and surpassing the 1995-1996 Bulls. Interestingly, both dynasties had dramatic downfalls. The Warriors fell to dead last in the Western Conference in 2020 and after their second mini-dynasty, the Bulls fell to dead last in the East in 1999.

Semifinal #2: 1983-1987 Lakers (#4) vs. 1999-2003 Lakers (#7)

The Lakers franchise has always been filled with NBA legends. This matchup features five Hall of Famers and four No. 1 overall draft picks in Magic Johnson, Kareem Abdul-Jabbar, and James Worthy for the 1980s Lakers, and Shaquille O’Neal and Kobe Bryant for the 2000s edition. Among this group there are 11 MVP awards, 12 Finals MVPs, and 71 All-Star appearances. While four of these players are considered to be Top 10 players of all time, most rankings have both Magic and Kareem ahead of Shaq and Kobe. The 80s Lakers also had more depth than the 2000s teams, as in most seasons, five other players averaged at least 10 points per game in addition to Kareem and Magic. However, most of the early 2000s Lakers teams only had one player (Derek Fisher) average more than 10 points per game. In addition, the 80s Lakers also dominated the regular season more, finishing first in the Western Conference for 9 consecutive seasons. Meanwhile, the early 2000s Lakers only topped the West once, consistently finishing behind Gregg Popovich’s Spurs. This is a close one, but Magic hits a clutch skyhook to advance the 80s Lakers to the NBA Region finals. 

NBA Region Finals: 2014-2018 Golden State Warriors (#1) vs. 1983-1987 Lakers (#4)

There are lots of similarities between these two dynasties. Both had Big 3s in Magic, Kareem, and James Worthy and Kevin Durant, Steph Curry, and Klay Thompson. Both had a worthy rival whom they often met in the NBA Finals in the Larry Bird Celtics (three Finals meetings) and the LeBron James Cavaliers (four Finals meetings). However, these Warriors dominated the postseason on another level. In their respective five year spans, the Lakers went 67-29 (.700) in the playoffs and the Warriors went 77-28 (.733). This includes their 2017 postseason, in which they lost one single game (against the Cavaliers in the finals). The Warriors also had a higher blended Elo throughout their dynasty (1789) than the Lakers (1715). Perhaps another Lakers dynamic duo in LeBron James and Anthony Davis can repeat as champions in 2021, pushing the Lakers past the Celtics in total championships, but the Warriors advance to the Final Four in this dynasty bracket. 

MLB Region

Play-In Game: 1987-1991 Oakland Athletics (#17) vs. 2004-2008 Boston Red Sox (#20)

These A’s had some great players. They had three MVPs, including all-time stolen base leader Rickey Henderson, pitcher Dennis Eckersley, and outfielder Jose Canseco*. They also had Mark McGwire*, who led the league in home runs (49) when he won Rookie of the Year in 1987: 10 years before he broke the single-season home run record, 20 years before Barry Bonds broke his record, and 23 years before McGwire admitted to taking PEDs. Former Moneyball Athletics general manager Billy Beane also played on this team. But while they reached three straight World Series, they lost two of them and barely reached .500 in the other two years of this “dynasty”. Meanwhile, Boston consistently played well in the regular season, went two for two in the World Series, and has a narrative that no team can match. This matchup goes to the Boston Red Sox that broke the infamous Curse of the Bambino (won by another analytics-savvy GM in Theo Epstein).

Semifinal #1: 1996-2000 New York Yankees (#5) vs. 2004-2008 Boston Red Sox (#20)

This is our first real-world rivalry matchup in arguably the greatest sports rivalry of all time. From 1996 to 2000, New York had a 40-27 record against the Sox. In the second five-year span, they still had an ever-so-slight winning record of 51-49. However, in the 2004 ALCS, the Red Sox overcame a 3-0 deficit (the only time in MLB history) against the Yankees en route to their first World Series in 86 years. There won’t be any big comebacks this time, as the Yankees advance. They were better than the Red Sox in both the regular season and the postseason, and racked up four titles in five years compared to Boston’s two.

Semifinal #2: 1972-1976 Cincinnati Reds (#8) vs. 2016-2020 Los Angeles Dodgers (#14)

The Dodgers of this decade were known as the team that just couldn’t win the World Series until they finally won this past 2020 season. They have won 8 consecutive division titles, the third-longest streak behind the 1991-2005 Atlanta Braves and the 1998-2006 Yankees. Similar to the 1987-91 A’s, their 2020 roster had three MVPs in Mookie Betts, Cody Bellinger, and Clayton Kershaw. The only thing keeping them from advancing is history. The Big Red Machine boasted had four MVPs in Joe Morgan, Pete Rose, Johnny Bench, and George Foster, as well as Hall of Famer Tony Perez (notably all hitters). The Reds also have the best regular season score of any MLB dynasty, and the second highest regular season score (99.4) of any team in this bracket.

Both Cincinnati and Los Angeles had two seasons with over 100 wins, but today’s MLB teams are much more stratified and the league has less parity. In 1975, the Reds were the only team with over 100 wins and only one team (Detroit Tigers) had fewer than 60 wins. In 2019, the Dodgers were one of four teams (New York Yankees, Minnesota Twins, Houston Astros) with over 100 wins and four teams had fewer than 60 wins (Detroit Tigers, Baltimore Orioles, Kansas City Royals, Miami Marlins). This “tanking” trend is becoming more prevalent across the sports world, causing more separation between the best and worst teams in each league. This means that the Reds’ win total of 108 in 1975 is significantly more impressive than the Dodgers’ 106 wins in 2019. The gap between their win totals might be just two games, but the adjusted score margin is much wider (99.4 vs. 91.4). Still, this matchup might not be completely settled yet, as the Dodgers are the favorites to repeat as champions and continue their dynasty. As of now though, the Reds prevail.

MLB Region Final: 1996-2000 New York Yankees (#5) vs. 1972-1976 Cincinnati Reds (#8)

The Reds were the more dominant regular season team, as they led the MLB in wins in four of the five years of their dynasty. Meanwhile, the Yankees only led the league in wins once, and averaged 4th in the league in wins. However, that one time was one of the greatest seasons in MLB history. The 1998 Yankees reeled off 114 wins, the second-most in a season behind the 2001 Seattle Mariners (116 wins). What puts the Yankees over the hump is their outstanding postseason performance, winning 4 World Series. The Yankees are one of only two MLB teams to three-peat since the Expansion Era of the 1960s (along with the 1972-74 A’s). These Reds did win two World Series, but the Yankees blow them away in Postseason Score (84 to 64). And while both teams were loaded with Hall of Famers, the Yankees have the two most unanimous in Cooperstown history in Mariano Rivera (100% vote) and Derek Jeter (99.7% vote). Mariano Rivera completes the save, advancing the Yankees to the Final Four.


We now have the first two representatives in the Final Four: the 2014-2018 Golden State Warriors for the NBA and 1996-2000 New York Yankees for the MLB. There are two tickets still left to punch from the NFL and NHL. Check out our next article on the best NFL and NHL dynasties to see who advances.

Editor’s Note: Do you think we left out a dynasty? Which dynasty do you think will win in the Final Four? If you have questions about this article, 
please feel free to get in touch with David at 

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