Do the 1999 Chicago Bulls win the title with MJ, Pippen and Co.?

The Chicago Bulls went their separate ways following their 1998 title, but their chances at a four-peat is a question that looms even all these years later.

Across the rich history of the NBA, several different factors have contributed to the downfall of some of their most notable dynasties.

The Boston Celtics of the 1950s and ’60s aged out of their ability to contend. The early 2000 Los Angeles Lakers were dismantled thanks to unsalvagable friction between their two leaders. Both the Miami Heat and Golden State Warriors of the previous decade saw their status take a hit after the allure of playing elsewhere grew too large for their respective best players.

For the Chicago Bulls of the 1990s, the culprit came from within the front office, who sought to voluntarily strip away the pieces that brought the franchise six championships in eight years.

Before the start of the 1997-98 season, Chicago general manager Jerry Krause made sure this season would be the last for head coach Phil Jackson with the Bulls, independent of results.

It was a trickle-down effect from there, one Krause was happy to watch unfold in pursuit of the chance to build a championship contender in a way that would earn him the credit he thought he deserved.

The Bulls would win the 1998 championship, but Michael Jordan had already made clear an unwillingness to play for any coach besides Jackson, who was only signed to a not-so-subtle one-year deal. So, he retired for the second time.

Already fuming at his status as one of the league’s most underpaid players and the organization’s indifference towards doing right by one of their greats, Scottie Pippen saw the writing on Chicago’s wall with both Jackson and MJ gone.

In his departure, Pippen made sure to get paid in the form of a sign-and-trade with the Houston Rockets that netted a much-deserved five-year, $67 million contract.

The final nail in the coffin for one of the NBA’s most revered dynasties, Dennis Rodman signed with the Los Angeles Lakers roughly one month later.

And suddenly, the league’s best team had tumbled down the hierarchy, winning just 13 games the following season while leaving open a championship door that had been under heavy lock and key in the presence of His Airness.

Had the organization not alienated each of those crucial pieces to perhaps the greatest teams of all-time, none would’ve likely had a reason to depart in their respective manners. But despite the dominance Chicago displayed under Jordan’s watch in the ’90s, the chances of a fourth-straight championship wouldn’t have been so reassuring.

The timing of Krause’s upheaval wasn’t coincidental. Before the 1997-98 season and certainly after Chicago wrapped up its sixth championship, signs of demise were easy to see.

Pippen had undergone surgery on his left foot before the season, causing him to miss nearly three months of action. Throughout most of the Finals series with the Utah Jazz, he dealt with searing back pain that limited him to just 25 minutes in the series-clinching Game 6 while darting between the court and locker room to receive treatment.

Jordan seemed fine by playing all 82 regular-season games and dragging Chicago to the title amidst the surrounding injuries by averaging 41.5 playoff minutes per game. And yet, one had to wonder how much more his body could take at his level of play and the amount his psyche could handle as perhaps the world’s most famous celebrity.

Rodman was 37 with a physical brand of playstyle that could only remain steady for so long. He even began coming off the bench in the Eastern Conference Finals against the Indiana Pacers — Game 3 excluded — and did so through the Finals.

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Those same Pacers took the Bulls seven games, where Chicago escaped Game 7 with a five-point win.

Indiana returned the following year and won a conference-best 33 games in the lockout-shortened 50-game season, tied with the Miami Heat — and a pretending Orlando Magic team.

That Heat team gave up the second-fewest points per game on the season, boasting a duo of the quick-footed Tim Hardaway and Alonzo Mourning, who finished second in MVP voting with the inside prowess to wreak havoc on Chicago’s weak frontcourt.

Even more daunting than the playoff picture that also included the eventual Eastern Conference champion New York Knicks — what Chicago’s presumed presence in the playoffs means for the eighth-seeded Knicks is worth mentioning — were the roadblocks in place thanks to the lockout that began the season in February and condensed the season into the aforementioned 50 games.

The 50 games were played across just 90 days. This, after only 12 days for a training camp where some rosters weren’t even fully set due to the simultaneous presence of free agency. Chicago had two instances of three games in as many nights along with plenty of back-to-backs and three games in four nights.

Jordan was the master at using his mind to push his body to places it thought could never be reached. It’s what gave him the strength to push through the flu in Game 5 of the 1997 Finals.

But in a season that claimed many injuries, a 35-year-old MJ coming off three title runs would have to feel the physical effects of a challenge no human body was prepared to withstand. The same certainly goes for Pippen and Rodman dealing with physical limitations of their own.

Had the Bulls emerged from the east, the eventual champion San Antonio Spurs would await in the Finals.

San Antonio wouldn’t have many answers for Jordan, but the same goes for the Bulls and the frontcourt twosome of Tim Duncan and David Robinson.

Remember, whatever Chicago accomplishes in this hypothetical season falls under the assumption that their bodies hold up long enough for them to go out and do it, not exactly guaranteed under the circumstances.

Betting against Jordan for most of the ’90s didn’t work for anyone — 1990 and a half-baked 1995 aside. With that logic, doing so in 1999 probably wouldn’t have yielded positive results either.

Whatever the odds were, the Bulls earned the right to play them for a chance to become just the second team to ever win four straight championships. That they couldn’t remains an egregious showing of ego on the part of Krause, because as Jordan put it during the press conference following his fifth title, “we’re entitled to defend what we have until we lose it.”