Had a discussion with @NickyKM92 earlier when it pertains to the Bulls extending their run past 1998. The following are the possibilities that we discuessed the could have happened had everything fallen into place for everyone to stay through to the end of 1999/2000.
It must be said, that all of this happens using a heap of "what if" scenarios; Scottie staying and not worried about money, Phil staying despite the rift with Krause, Rodman not giving the game away, and the roster being in tact with a commitment to the following season.
The big thing for the Bulls was their lack of offensive production outside of Michael. This would mean that there would have to be changes made to some of the squad in order to keep the roster strong in the immediate while being sustainable in the immediate future.
The best free agent's available in the off-season leading into 1999 (of those who signed new deals before the Feb tip-off) were Mario Ellie, Dell Curry, Vlade Divac, and Antonio McDyess. Not standouts, but players capable of filling a roll and helping out moving forward.
The Bulls drafted Corey Benjamin that season, and while the evidence of him talking trash to Jordan showed he got schooled, you have to think that things change with a returning roster.
Through the playoffs, the following players recieved the majority game time;

Haper.
MJ.
Pippen.
Kukoc.
Longley.
Rodman.
Kerr.
Burrell.

Players such as Wennington, Simpkins, Brown, and Buechler played sparingly at best.
To look at that roster, knowing your free agents, the aging roster, and the fact that there is a need to transition through while being a champion, the Bulls would have been primed to secure a capable big, along with scome scoring and floor stretching.
This would see the ideal chance to secure (of those 4 FA's mentioned above) Mario Ellie, Dell Curry, and Antonio McDyess. You could freely move Simpkins, while keeping Wennington or Buechler for short corner relief and size, with Brown as a part of the 15-man roster.
So, you could see a list heading into 1999 as;

Harper
MJ
Pippen
Kukoc
Longley
Rodman
Kerr
Burrell
Ellie
Curry
McDyess
Wennington
Benjamin
Buechler
Brown
Again, remember, this is all "what if" and knowing how Krause blew up the team, this would have been almost a 180 from his thinking.
1999 saw the Eastern Conference look like this.

Miami
Indiana
Orlando
Atlanta
Detroit
Philadelphia
Milwaukee
New York
The following players, hypothetically now reamining or signed with the Bulls, were on new East teams or retired.

Michael Jordan (retired)
Scott Burrell (New Jersey)
Jud Buechler (Detroit)
Dell Curry (Milwaukee)
The Western Conference looked like this:

San Antonio
Utah
Portland
Los Angeles
Houston
Phoenix
Sacramento
Minnesota
The following players, hypothetically now reamining or signed with the Bulls, were on new West teams or retired.

Scottie Pippen (Houston)
Dennis Rodman (Los Angeles)
Steve Kerr (San Antonio)
Mario Ellie (San Antonio)
Antonio McDyess (Denver)
Luc Longley (Phoenix)
And the Bulls kept or drafted:

Ron Harper
Randy Brown
Toni Kukoc
Bill Wennington
Corey Benjamin.
With New York out of the picture, one would assume that the three leading teams in the East in Chicago, Indiana, and Miami all make it to the second round, along with either Philadelphia or Atlanta. Either way, the feeling for me is the Bulls make the ECF.
From there, it's a contest against either Miami or Indiana. I feel the Pacers would be the match-up again as the Heat likely burn out early again. Another tight series but the Bulls move forward. Aged? Sure, but the Pacers began a decline as well.
Now the question is who comes out of the West. For me, the Spurs would make it again. While no Mario Ellie and Steve Kerr changes the shooting off the bench, there isn't a reason to say they couldn't make up for it with the form Duncan was in (MVP-Level)
The big test is in fact in the finals; Duncan and Robinson would be the best big combination the Bulls faced in their time, and certainly the best defensive combo IMO. However, the Bulls had a game style to negate the effects of opposing big men (Ewing, Mourning etc).
With not as much stretch scoring from Kerr and Ellie, and the Bulls track record, I feel they get over the line. Duncan has a great series, Finals MVP stuff as he almost always did, but I'm not sure the Spurs perimeter can mix and match with two guys still in All D 1st team form.
Now, the next question; what would the Bulls do following 1999. Again, a lot of this is hypothetical and staying on the note that everyone is on board until the train derails itself instead of not being allowed to leave the station.
At this stage, one would assume that things are just as strained to start 1999/2000 as they were to start 1997/1998; Scottie wants to be paid, Phil is over it all, and Michael wants to go until he's knocked off.
This is where the Bulls should again look to the contingency plan, the free agent market, and work on the premise that this is truly "The Last Dance." They could work on the idea that Phil, MJ, Scottie, and Dennis are done after this season.
Handling this is delicate, but with smart free agency acquisitions leading would alloow them to be major players heading into the Summer of 2000 and free agency.
The two best free agents available after the 1999 season IMO were Bruce Bowen and Steve Smith. Smith proved a vital cog for Portland before stepping back to the bench to wind up his career, while Bowen developed into one of the best perimeter D players of his era.
While Elton Brand and Ron Artest were originally drafted by the Bulls back then, one would assume they are instead give the Spurs pick in which they selected Ginobili. I'm not saying Krause would have taken Manu, but his eye was always in Europe.
With Manu available that late, there isn't a reason this wouldn't have not been viable. While he wouldn't join the team immediately, his debut in the league a few years later would look genius after free agency.
The question from here is who takes what role on the team. Bill Wennington would be moved on, as would Randy Brown. Benjamin holds his spot, but can pretty much say goodbye at the end of the year.
The new 15-man roster for 2000 would look like;
Harper
MJ
Scottie
Rodman
McDyess
Kukoc
Kerr
Ellie
Curry
Longley
Smith
Bowen
Buechler
Burrell
Benjamin
2000 also has a major impact. Of the 15 players mentioned above to hold the list, only Corey Benjamin and Toni Kukoc remained. The rest were on new teams or retired. This has massive implications around the league, particularly in the West.
Los Angeles don't have Phil and Harper.
Portland don't have Scottie and Smith.
San Antonio don't have Ellie and Kerr.
Phoenix don't have Longley.
Denver don't have McDyess.
Dallas aren't wasting Rodman.

Over half the roster and the coach are in the West.
In the East;

MJ wouldn't be retired.
Curry isn't in Toronto.
Bowen isn't in Miami.

The outlook of their team and the league is a major change.
2000 becomes evident that this is the last run for the Bulls. With this roster, they can remain a threat in the East and in my mind would likely once again match up with the Pacers in the ECF. New York were again in the ECF that year, however they aren't making it.
The Pacers by 2000 weren't the team they were in 1998. Mark Jackson wasn't the same player, Jalen Rose had taken more of a role offensively, and Reggie Miller wasn't the same player. Dale Davis was an All Star, but the rest of the team wouldn't have shaped up to these Bulls.
The Bulls had strengthened perimeter D, a more competent big in McDyess, a still rebounding Rodman, spread scoring with their acquisitions, and importanly; MJ. The Bulls should have won 1998 in 5 games, this time they likely get it done in 5 or 6.
But who would they face? The Lakers without Phil weren't the same without him, and one has to wonder how Kobe and Shaq get on without him, let alone if Shaq is motivated for 200.
The Blazers would be without Scottie and Smith. Both proved to be the key cogs in the machine along with Rasheed Wallace, however they proved to be the key perimeter defenders for the team.
San Antonio, while without Kerr and Ellie, would still be a playoff team. However seeing as Duncan got injured, how far would they progress?
Sacramento are a factor here; young and talneted, do they take the step early seizing on the issues with the other three I mentioned above? Other west teams include Phoenix, Utah, Minnesota, and Seattle.
This one is a tough one. I'd say the Lakers likely pull through as history would suggest. A deep roster with the exclusion of Harper would have helped IMO.
But what is the final result? At this stage yoou'd have to be the bravest man on the planet, but with age a factor, Shaq and Kobe competing one on one, and the Lakers bringing a deep rotation, could they do the impossible?
Ultimately, the three big questions for this are; Can Shaq gain enough possessions to be a fctor down low on an aging Rodman with a double from McDyess? Can Kobe check his ego against MJ, and do the Bulls have the legs to get it done?
No matter the result of the series, knowing the mileage on the legs, allowing the team to go out on its own, Scottie wanting to be paid at least once for his career, and Phil having a desire to coach Shaq, the senior core of the team would be done IMO at the end of the Finals.
Departing the team would likely be the following;

Phil
MJ
Scottie
Rodman
Harper
Longley

The original starting five of the 72-10 team, signalling a ture changing of the guard.
With the team allowing an easy transition, the Bulls instead of becoming a franchise that no one wanted a piece of have become the premier franchise for all free agents.
Everyone knows the stories of the likes of Tracy McGrady and Kevin Garnett wanting nothing to do with the franchise, and the talks of Duncan joining McGrady and Grant Hill in Orlando. Maybe the Bulls could have been in those conversations at that time, too.
This is all a big "what if" scenario. But considering the simple moves that could have been made to at least maintain the roster and give the franchise the best shot of obtaining future free agents to stay in contention, you have to wonder how they squandered it so badly.
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