Ever since Michael Jordan and Scottie Pippen led them to their sixth championship in 1998, the Chicago Bulls have not found much success. There were some glimmers of hope with Derrick Rose and Jimmy Butler, but over the last eight seasons, Chicago has made the postseason only two different times and they have failed to win a playoff series since 2015.

Desperation is the word that comes to mind when evaluating the state of this franchise, as they truly need something good to happen to them entering the 2023-24 NBA season.

This organization is facing a crossroads this upcoming year. Two paths have presented themselves: one that leads to a rebuild and the other that leads the Bulls back to the playoffs. There really is no telling as to which path Chicago will go down this year, especially since there is no telling as to what their roster will look like all season long given trade rumors and injuries.

“We know we can do better, and we have to do better,” Vucevic told Yahoo Sports recently. “And we know it’s kind of our last chance as this core of guys to do something.”

Vucevic has been around the league for 12 seasons now and he's one of the veteran leaders of the Bulls. He's been a part of teams going through a rebuild, as well as those who are in contention for a playoff spot. Right now, there is a lot of uncertainty surrounding the Bulls and their current contract situations is why this season could be their “last chance” to do something.

Six-time All-Star DeMar DeRozan is in the final year of his contract and will be an unrestricted free agent in 2024. Two-time All-Star Zach LaVine recently signed a new five-year contract last offseason, but his name has been a hot topic of discussion in trade rumors given the organization's lack of success. While Vucevic recently signed a three-year, $60 million extension this offseason, his future is uncertain as well given the fact that he will be turning 33 in October.

The Eastern Conference also continues to grow and younger teams like the Indiana Pacers, Detroit Pistons and Cleveland Cavaliers have already begun to rise. The Bulls are stuck right in the middle of the pack and they are on the declining end of being real playoff threats.

Unless they can quickly turn around their recent misfortunes during the first several weeks of the 2023-24 season, the Bulls are destined to head towards a rebuild, one that could see the departures of Chicago's core in Vucevic, LaVine and DeRozan.