How Michael Jordan's best Chicago Bulls squad would have stacked up against the greatest NBA teams of all time

Over the course of his illustrious NBA career with the Chicago Bulls, Michael Jordan provided us with many memorable playoff matchups. There were those early battles with the "Bad Boy" Detroit Pistons, the Finals showdown against Magic Johnson and the Los Angeles Lakers, which served as a passing of the torch of sorts, and the back-to-back Finals meetings with the Utah Jazz to name a few.

Yet while the lore of the Jordan-era Bulls will live on forever, they were only at the peak of their power as a team for a finite amount of time. While the Bulls thoroughly dominated the majority of the '90s, there were plenty of other great championship teams -- before and after -- that didn't get an opportunity to square off against Chicago at the height of its powers. 

Shortly after the Bulls' dynasty came to an end, another powerhouse emerged in the Lakers, led by the lethal duo of Shaquille O'Neal and Kobe Bryant. It would have been something to see Jordan's Bulls and Bryant's Lakers go head-to-head. Same for the Golden State Warriors, specifically the superteam consisting of Stephen Curry, Kevin Durant, Klay Thompson and Draymond Green. That would have been a battle. 

So what if Jordan's Bulls had the chance to go up against some of the other legendary NBA teams ever assembled? For this exercise, we'll match them up against five of the greatest teams we would have loved to see Jordan and the Bulls square off against in a postseason setting while Chicago was at its best. Considering the 1995-96 Bulls broke a league record by winning a franchise-record 72 games in the regular season and then only lost three playoff games before winning the title, we'll use that season's team to represent the Bulls at their very best. A glance at their '95-96 season:

  • Record: 72-10 (.878) | Offensive rating: 115.2 | Defensive rating: 101.8
  • Key players: Michael Jordan, Scottie Pippen, Dennis Rodman, Toni Kukoc  

As you can see, that Chicago team was dangerously good. That said, here are the five teams -- all NBA champions -- that we would have loved to see those Bulls battle against in a playoff setting:

1985-86 Boston Celtics

  • Record: 67-15 (.817) | Offensive rating: 111.8 | Defensive rating: 102.6
  • Key players: Larry Bird, Kevin McHale, Robert Parrish, Dennis Johnson, Bill Walton 

Despite the fact that both Chicago and Boston were in the same conference and made annual trips to the postseason throughout the 1980s and early '90s, Michael Jordan and the Bulls only ran into Larry Bird's Celtics twice in the playoffs -- in 1986 and 1987. Both meetings occurred in the first round of the postseason, and the Celtics swept both series, 3-0.

Jordan was still just a pup in the league at that point, though, as these meetings occurred during his second and third seasons in the league, respectively. He wasn't fully developed physically, or as a player at that point, and he hadn't yet learned what it took to win at the highest level. Also, Jordan didn't have his supporting cast. Both of Jordan's postseason matchups against the Celtics came before Scottie Pippen was on Chicago's roster, and obviously well before Dennis Rodman was added to the mix. It was also before Phil Jackson was brought on to coach the team.

While Jordan's Bulls weren't in full form yet, the Celtics were at their zenith as a team. They went to four straight Finals from 1983 to 1987, winning two of them. The 1985-86 Celtics had five future Hall of Famers on the roster -- Larry Bird, Dennis Johnson, Kevin McHale, Robert Parish and Bill Walton -- and won 67 regular-season games. Boston also lost just three times during the postseason on its way to a title. As such, it is widely regarded as one of the best teams in NBA history, and arguably the best Celtics squad of all time.

So while Jordan and the Bulls technically did face off against the '85-86 Celtics in the playoffs, it would have been better and so much more exciting to see the two legends in Jordan and Bird square off against each other while both were in the midst of their primes and equipped with their best supporting casts. The chess match between the two all-time legends would have been fascinating to see. In addition to getting to see peak Jordan and peak Bird go head-to-head, it would have been great to see Pippen try his hand at slowing Bird, and Rodman battle on the boards against the likes of Kevin McHale and Robert Parrish. The Celtics got the best of the Bulls in '86, but things may have turned out differently in a matchup between that Celtics squad and the Bulls' best. 

1986-87 Los Angeles Lakers

  • Record: 65-17 (.793) | Offensive rating: 115.6 | Defensive rating: 106.5 
  • Key players: Magic Johnson, Kareem Abdul-Jabbar, James Worthy, Michael Cooper

By the time Jordan and the Bulls got to match up against Magic Johnson and the Los Angeles Lakers in the postseason -- the 1991 NBA Finals -- the "Showtime" Lakers were on their last legs. At that point, Magic and the Lakers were coming off a decade straight of deep postseason runs, and while still great, they just weren't the same squad that they once were. Kareem Abdul-Jabbar was gone, while Johnson and James Worthy had both declined athletically.

The Lakers were still good enough to win 58 regular-season games during the 1990-91 campaign and advance all the way to the Finals, but once there they couldn't keep up with the young and hungry Bulls, who won the series in five games. It was Chicago's only Finals series during the decade that didn't stretch to six games. For the Lakers, the loss to the Bulls in 1991 proved to be the end of an era, as it was the last time that they would make the Finals in nearly a decade. It was also Magic's last postseason run, as he retired from the NBA prior to the start of the 1991-92 season.

While it was great to get to see Jordan and Johnson go at each other on the highest stage, it would have been so much better -- and likely closer as a series -- if Johnson was still in his prime athletically, and still had his go-to guy in Abdul-Jabbar, as he did in '87. After winning 67 games during the regular season, the Lakers blew through the postseason, losing a total of just three games on their way to a title. Would anyone on Chicago's front line have been able to slow Abdul-Jabbar? As a team they never had to face a dominant center during any of their six Finals matchups, so it certainly would have been a tough test.

2000-01 Los Angeles Lakers

  • Record: 56-26 (.683) | Offensive rating: 108.4 | Defensive rating: 104.8 
  • Key players: Shaquille O'Neal, Kobe Bryant, Derek Fisher, Horace Grant

Two years after Jordan won his sixth and final title with the Bulls, the NBA's next dynasty emerged in the form of the Los Angeles Lakers. Led by Shaquille O'Neal and Kobe Bryant, the Lakers made four Finals appearances and won three titles from 2000 to 2004 (Bryant would go on to lead the Lakers to two more titles in 2009 and 2010 after O'Neal was traded). The tandem of Shaq and Kobe, much like Michael and Scottie, quickly established themselves as one of the most dominant duos in league history in the process.

They had a better regular-season record the year before (67-15 compared to 56-26), but the 2000-01 Lakers were one of the most dominant playoff teams of all time. They went 16-1 in the postseason on the way to their second straight title, and if it weren't for a gutsy 48-point performance from the league's MVP at the time -- Allen Iverson -- in Game 1 of the 2001 Finals against the 76ers, they would have gone undefeated. Given their dominance, it would have been extremely interesting to see how they would have fared against the Bulls at their best. 

Jordan and O'Neal have some playoff history, as Shaq's Magic defeated Jordan and the Bulls in the Eastern Conference semifinals in 1995 before Chicago bounced back to sweep Orlando in the 1996 conference finals. Still, O'Neal didn't fully hit his prime as a player until he signed in Los Angeles, where he blossomed into arguably the most dominant big man the league has ever seen. Watching the most dominant scorer and perimeter player go against the best big man in the game while both in their primes would have been a sight to see. 

Then there's the Kobe Bryant angle. Bryant completely modeled his game after Jordan, and as a result, he was the closest clone to Jordan that we've ever seen -- and likely ever will. Bryant's game mirrored Jordan's, and though Bryant wasn't quite as great as M.J., he was damn close. Both being lockdown perimeter defenders, they assuredly would have guarded each other in this matchup, with both trying their hardest to prevent the other from having a big night on the offensive end. Watching those two fierce competitors go head-to-head for a title would have been fascinating. 

No matter who came out on top of this hypothetical bout between the Bulls and Lakers, Phil Jackson would have walked away with a W either way as he was the head coach of both teams. Talk about a resume. 

2012-13 Miami Heat

Like Jordan and Pippen, LeBron James and Dwyane Wade were one of the best duos of all time, even though they only played together for four years (four and a half if you count Wade's forgettable stint with the Cavaliers during the 2017-18 season). During their time together in Miami, James and Wade made four straight Finals appearances and won two titles. They were at their best during the 2012-13 season when they won a franchise-record 66 regular-season games (including 27 straight at one point) and went on to best the San Antonio Spurs in the Finals.

Considering the fact that many consider Jordan and James to be the two best players in league history, a postseason matchup between them would have been one for the ages. The two all-time greats would have ended up matched up on each other for stretches, as James often served as the de facto ball-handler for the Heat. While James would've had the size advantage, Jordan regularly took it to players as big, or even bigger, than James so he certainly wouldn't have been intimidated. Both were elite defenders in their prime, so the matchup likely would have came down to which one could do a better job of slowing the other. 

Plus, Pippen and Wade are arguably the two best No. 2s of all time, and both would have found a multitude of ways to impact the series. The same can be said for Dennis Rodman and Chris Bosh, as Rodman certainly would have tried his best to irritate Bosh. Both teams had solid veteran role players surrounding their stars, and overall it likely would have been a pretty even series. It's too bad we'll never get to see it play out, because the outcome could've gone a long way toward settling the incessant debates regarding who the better player is between Jordan and James.   

2016-17 Golden State Warriors

  • Record: 67-15 (.817) | Offensive rating: 115.6 | Defensive rating: 104.0
  • Key players: Stephen Curry, Kevin Durant, Klay Thompson, Draymond Green, Andre Iguodala  

When ESPN recently re-ranked the best teams of all time, the 2016-17 Warriors were the only team to rank ahead of the 1995-96 Bulls. Their explanation:

After failing to translate an NBA-record 73 wins into a title the previous season, the Warriors slacked -- relatively -- after adding Kevin Durant to the core of the 2015 champions, winning only 67 games. Come playoff time, Golden State lived up to its potential, coming within a game of completing the first unbeaten postseason in NBA history. The Warriors settled for 16-1, and their adjusted playoff differential ranks second all time behind the 2001 Lakers.

While Golden State won more games (73) the previous season -- breaking the Bulls' record 72-win season -- the '16-17 Warriors were virtually the same team as the year before. The difference? They added a future Hall of Famer still in his prime in Kevin Durant. That iteration of the Warriors had one of the most explosive offensives of all time, and they were also dominant defensively.

Though there was no such thing as stopping Michael Jordan, the Warriors had several capable defenders -- Thompson, Iguodala, Durant -- that they could have shuffled onto Jordan to potentially slow him down. Thus, Steph Curry likely wouldn't have spent much time, if any, guarding Jordan, as M.J. would have proved to be too big and strong for Curry to handle. 

On the flip side, if anyone had a chance of stifling the Splash Brothers, it would have been the combination of Jordan and Pippen. Jordan almost certainly would have spent a substantial amount of time dogging Curry, and making sure that the two-time MVP didn't get any easy looks. Ron Harper probably would have drawn Thompson for extended stretches, while Pippen likely would have been tasked with slowing Durant. All of these matchups would have been fascinating to see. Plus the battle of the boards between Rodman and Draymond Green, and the trash-talking between the two, would have been epic. 

Michael Kaskey-Blomain covers the NBA for CBS Sports. He has covered the league in some capacity since 2009 for a variety of outlets including Philly.com, ESPN 97.3, and 247 Sports. Michael hails from... Full Bio

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