I’ve been a Bulls fan since 2014. To put that in perspective, that’s the year Michael Carter-Williams won rookie of the year as a Philadelphia 76er. He turned 31 last week. Over those past eight years, I’ve never seen a Bulls team in such a unique situation.

If the performance during the first half of last season is any indication of this year, the Bulls have a higher potential for success than I’ve ever seen before.

But with aspirations for winning also comes a potential for failure. The Bulls just signed Zach LaVine to a five-year $215 million contract, so the potential risk is high.

The Bulls went all-in as a contender, and they have a legitimate shot at it being successful. But if they fail, it’ll be a tough road back.  This next season could be one of the most pivotal for the Bulls over the next half-decade.

An Optimistic Outlook

DeMar DeRozan just received MVP votes in what was probably the best season of his career. Zach LaVine was just named to his second All-Star game and is just getting started.

For much of last season, the Bulls were oscillating between the first and second seed in the Eastern Conference. The additions of rookie Dalen Terry and veteran Andre Drummond will only fill in gaps and make them even better.

Much of last year was spent building team chemistry as the Bulls acquired a new number one option in DeRozan. Now, Head Coach Billy Donovan can spend his time turning the team into a championship contender.

As the Bulls work to be better than last season, they may very well be one of the better teams in their conference. It’s the first time they’ve been in this situation in a long time, and the potential for greatness is evident.

A Pessimistic Perspective

For far too much of the past eight years, the Bulls have been sitting around the 10th or 11th best team in the East. It’s been a terrible situation, where there was essentially no opportunity for a low draft pick, yet also no chance for playoff contention.

Last year, the Bulls went all in, making it to the sixth seed and a first-round exit in the playoffs.

It wasn’t bad enough to call them a failure, but not good enough to call it a success. Sadly, it looks like they’re only going downhill from there.

Starting point guard Lonzo Ball remains injured. His exit last season was a large reason why the Bulls lost so many games later in the season. This season, it looks like they’ll be losing those same games, only earlier.

The failures of the Bulls over the past few seasons have meant nobody has been able to prove themselves in the playoffs. The exception is veteran DeMar DeRozan, who, while experienced in the playoffs, has been anything but successful.

With the Cavaliers’ addition of Donovan Mitchell, and the Nets’ addition of Ben Simmons, the Bulls could easily slide down to the eighth or ninth seed in the East once again.

The Season

The Bulls earned themselves three wins and only one loss during the preseason, including a 23-point victory over the Milwaukee Bucks. The regular season starts on Oct. 19 against the Miami Heat.

But even so, they’ll be about the only Chicago basketball team worth watching until the beginning of March Madness, and their unique situation may very well make them one of the most interesting teams in the league to keep an eye on.