As with the other posts, I'm going to discuss the past, present, and future of the Bulls.
The Bulls don't have near the history of the Bears and Cubs (in terms of years in existence), but they have more true championships than both organizations (yes, the Bears have 9, plus one Super Bowl, but those 9 came prior to the merger).
The Bulls are a rarity in professional sports, as they experienced success immediately upon their entrance into the league in their expansion season of 1966-1967, and they qualified for the playoffs. They were a fairly successful team from that point through the late 1970s with the likes of Jerry Sloan, Norm Van Lier, Chet Walker, and Bob Love, but they fell to the bottom of the league in the late 1970s and early 1980s.
The poor finishes were actually a blessing in disguise as they led the Bulls to selecting arguably the greatest player of all-time in the 1st round, 3rd pick overall of the 1984 NBA Draft, Michael Jordan
Jordan made a difference almost immediately, leading the team to the playoffs in his first season. They would go on to make the playoffs during the next 6 seasons before finally breaking through with a championship in the 1990-1991 season against the Lakers, then proceeding to 3-Peat, when Jordan suddenly retired from the game following the 1992-1993 season following his father's murder.
*unsubstantiated rumors stated that Jordan was actually forced to "retire" (though it was a rumored 1 year suspension) by David Stern as punishment for his involvement in gambling that could've potentially brought down the NBA. It was rumored that the time that his father's murder was carried out by thugs looking to make a point to Jordan to pay up on his gambling debts. However, absolutely none of this makes sense, given the fact that Jordan now is the majority owner of the Charlotte Bobcats. David Stern, and the NBA would simply never allow him to own a team if the rumors were actually true.
Jordan came back at the end of the 1994-1995 season, leading the Bulls to the playoffs, but they lost. He returned for the 1995-1996 season as the Bulls added a key piece to their success, Dennis Rodman, and led the Bulls to another 3-Peat, before retiring yet again. This would end the Bulls reign at the top of the league.
It was rumored at the time that the Bulls GM Jerry Krause did not get along with many of the coaches (especially Phil Jackson) or players, and it was his decision not to pay Phil Jackson that led Jordan to retire, and the subsequent mass exodus of players from the team. In fact, the last remaining players from the championship teams were Ron Harper, Randy Brown, Toni Kukoc, Dickey Simpkins, and Bill Wennington
But Krause likely wasn't the only factor in the mass exodus, as the NBA had a lockout during the 1998-1999 season, which led to just a 50 game schedule.
Even so, it was Krause's ill-advised hiring of his buddy, Iowa State University head coach, Tim Floyd, that resulted in terrible finishes the next 6 seasons, and ultimately led to Krause resigning from his position. It wasn't until the Bulls hired John Paxson, who subsequently hired Scott Skiles, a hard-nosed, defensive-minded coach, that the Bulls returned to respectability, making the playoffs his first 3 seasons on the job. Skiles was inexplicably fired over Christmas during his 4th season as head coach, and the Bulls would go on to hire a very inexperienced Vinny Del Negro as their coach.
When the Bulls hired Vinny Del Negro for the 2008-2009 season, it was assumed that the young coach would be able to lead a young team for years to come. However, what many people didn't know is that Del Negro wasn't even close to being the first choice for head coach of the team. The Bulls originally wanted to interview Tom Thibodeau , but since the Celtics were in the playoffs, they weren't allowed to interview him, and other teams were filling vacancies very fast. They were forced to make a decision, and they ultimately decided against waiting.
Del Negro did a very poor job of communicating with both management and the players, and GM John Paxson did not appreciate his arrogance, especially when it came to handling the injured Joakim Noah's excessive minutes upon his return from injury.
The Bulls fired Del Negro after the 2009-2010 season, and finally got their man in Thibodeau, who has thus far led the team to a 45-18 record, which, at present, is good enough for 2nd place in the Eastern Conference.
A good reason for the Bulls' success this year was their selection of Derrick Rose in the 2008 NBA Draft. His selection, combined with the strategic hire of a defensive-minded coach like Thibodeau, and the signings of very good complimentary players cush as Carlos Boozer, Kyle Korver, Ronnie Brewer, CJ Watson, Kurt Thomas, and the defensive-minded Keith Bogans have been very instrumental in the team's success.
We'll see how far the Bulls can go in the playoffs this year. It will depend a lot on their health, and the ability of the complimentary players to hit shots when Rose is double-teamed. It will also depend on their defense, as the Bulls tend to struggle when the games become shoot-outs. Their success rate improves dramatically when they hold their opponent under 90 points.
The Bulls are better positioned than most teams, because they have most of their lineup locked up long-term to team-friendly contracts with Boozer, Noah, and Deng. They will need to extend Rose soon, so they'll have to get a little creative, but in general, they are well-positioned for the future.
The Bulls also hold multiple first round picks over the next few seasons, which will also help them add depth via trade, or make multiple selections to get younger.
It is abundantly clear that the Bulls are going to need some help at shooting guard next year. Unfortunately, there are no good options in the upcoming free agent class, so their best bet to find help is via the draft, or possibly via trade. The Bulls were rumored to be in discussions with the Rockets and Grizzlies this year in trades for Courney Lee and O.J. Mayor respectively. But both teams wanted big men, and the Bulls refused to give up Omer Asik or Taj Gibson in any trade. They have also been rumored to be interested in Rudy Fernandez of the Blazers in the past. Personally, with Boozer locked up long-term, I would've dealt Gibson, but the Bulls are probably thinking that come Draft Day, there will be lots of guys available, and trades to be made, so perhaps they felt it was best to hang onto him until that point.
It's also abundantly clear that the Bulls prime competition for years to come will be the Miami Heat and New York Knicks. The Heat, with Wade, James, and Bosh locked up long-term, would require defensive height to counter their offense, while the Knicks require a quick defense to counter their fast-paced offense under D'Antoni. The Knicks, however, really only have Stoudemire and Anthony locked up long-term, and both of them are relatively indifferent on defense, so it'd appear the best way to counter them would be to have a high-powered offense of your own, and a taller lineup to box out and get rebounds.