The great Bulls dynasty of the 1990s ended abruptly but on a high note. Following their hard-fought NBA Championship win in 1998, Phil Jackson and management couldn't come to an agreement and they decided it was time for him to recharge, taking a step away from basketball. With their leader deciding to get out of the game, Jordan decided to call it quits again. With Jackson and MJ gone, the Bulls front office started their rebuild, trading away Scottie Pippen and not re-signing Dennis Rodman.

One of the great "What ifs?" in NBA history is what would've happened if the Jordan-Pippen-Rodman Bulls stayed together for a few more seasons?

Well, one man seems to have a pretty good idea of how things would've gone if the band stayed together for several more years.

In that same interview on ESPN's 'The Jump', Pippen goes on to say that not only would the Bulls have dominated the lockout-shortened (50-game) 1998-99 season but they would've gone on to win 'at least two' more titles.

Pippen elaborated, "I would have loved to have challenged ourselves to a point to where someone could defeat us."

The 10-time All-Defensive first-team selection and Hall of Famer stated that the teams that gave he, Rodman, Jordan, and company the most problems were the Utah Jazz, who were in the same age bracket as the Bulls, if not older. And in the NBA postseason, we do see veteran teams give fits to younger, inexperienced squads, so 'Pip' may have a point. 


When Rachel Nichols brought up that the lockout-shortened season would've helped the "old man" Bulls keep their legs fresh, Rodman stated, "That makes me mad, man...we had legs for 50 games. My God."

The Bulls were obviously dominant but could a 33-year-old Pippen, 37-year-old Rodman and 35-year-old MJ really have won two more titles?

We took a look at how the Bulls would've stacked up with the 1999 and 2000 NBA Champions, and the matchups are highly intriguing. 

The 1998-99 NBA Champion San Antonio Spurs were led by a ridiculously effective frontcourt of David Robinson and Tim Duncan. In the 1999 NBA Finals the Robinson-Duncan duo combined for 44.0 points, 25.8 rebounds, 4.8 assists, 2.0 steals and 5.2 blocks per game. They dominated the Patrick Ewing-less New York Knicks but the Bulls would've presented a much different challenge. 

Similar to the Utah Jazz (and pretty much every team in the league if we're being honest), the Spurs didn't have any single player who could be looked at like a clear-cut perimeter stopper. This brings up serious issues when matching up with a Bulls team that was getting 64.4 points per game from the trio of Toni Kukoc, Pippen and Jordan. On the flip side, the Spurs would've had a clear advantage on the inside.

The Bulls were outrebounded in both the 1997 and 1998 NBA Finals, and that edge on the glass is exactly what helped Utah extend those series to six games each time. Rodman is, of course, one of the greatest rebounders of all-time and was quite adept at guarding up a position (i.e. guarding much bigger players). So when factoring in Rodman's skillset and the way the Bulls would aggressively double-team Karl Malone in their series against the Jazz, the Bulls would likely have the advantage because at the time—despite being a player who was clearly prepared for high-pressure moments—Tim Duncan was only 22 years old.

For further examples that an experienced bunch would've taken down that Spurs team, look no further than the 1998 Western Conference Finals, in which the John Stockton-Karl Malone Utah Jazz that lost to the Bulls took down the Spurs 4-1. But when we look at how an aging Bulls squad would have faced off with the 2000 Los Angeles Lakers, things get a bit murky. 

The starting lineup of the Lakers was: Ron Harper, Kobe Bryant, Glen Rice, and '00 MVP Shaquille O'Neal.

The most interesting parts of this hypothetical matchup are how familiar the Lakers would be with the Bulls considering the presence of Harper in the lineup, the matchup of Shaq vs. the Bulls bigs and of course, what would've likely been a legendary battle between Jordan and a then 21-year-old Bryant.

Harper likely wouldn't have had an incredible impact, as the Bulls' triangle offense deemphasized the importance of a top-notch point guard. But the O'Neal-Bryant tandem had enough talent and skill to potentially overwhelm an aging Bulls team. 


Keep in mind that O'Neal led the charge (24.3 PPG) when the Orland Magic took down the MJ-led Bulls in the 1995 Eastern Conference Semifinals. Chicago's center rotation (Bill Wennington, Luc Longley) was essentially the same in '98 as it was in '95, so a slightly older and wiser O'Neal certainly would've again been able to post gaudy numbers against the Bulls. But Rodman, who was not on the '95 Bulls, had a reputation as someone who could give much bigger matchups fits, even the massive O'Neal, so there is a case to be had that the Bulls could've slowed him down.

So it all comes down to Kobe Bryant vs. Michael Jordan. 

The two legends faced off less than 10 times during their respective NBA careers and while '00 Bryant had not developed his 'Mamba Mentality' yet, he was fresh off an All-Defensive first-team selection while also being a 20+ PPG scorer. In '98, a 34-year-old Jordan put up 32.4 PPG on a 54.5 percent true shooting percentage, so he was still in top form. 

Ultimately, Bryant's athleticism would have played a major part in the Lakers' effort to slow MJ down, but we have seen over 13 different postseasons (33.4 PPG career playoff scoring average, No. 1 all-time), that there is no such thing as "slowing MJ down." 

The pure dominance of Shaq—and the fact that the Lakers would've had homecourt advantage—makes them look like the favorites, but Pippen, Rodman, and Jordan could easily frustrate O'Neal, forcing him to be more of a passer and high-volume free throw shooter.

We're taking the Bulls in seven games over the 2000 Lakers with an acknowledgment that it would be a hard-fought series, so maybe Pippen wasn't off with his prediction of two more titles had the Bulls dynasty stayed together longer.