Another week, another mailbag.

With so much speculation going on around the rest of the league, it’s becoming more and more unbelievable that the Chicago Bulls might again keep their group together.

Given where they are in the Eastern Conference landscape, their lack of flexibility to bring in more talent, can they even make the Play-In Tournament without making major additions? If not, what are we doing here?

With great questions coming in from Twitter comments, here are my thoughts on some interesting philosophical questions about the Bulls future.

@sincerestflatt:With the parity level of the current NBA, do you think running it back but getting some shooting could lead to a playoff berth next season?

I’d put it at 50/50…. to make the Play-In.

Barring major changes (and there may be major changes), the Celtics, Bucks and 76ers remain significantly better. The Cavs, Knicks, Heat and Hawks too. Depending on what happens with the Nets and Raptors, the Bulls are effectively in the same spot they were last year. The difference is, they have very few avenues to improve, while the rest of those teams still have upside.

That’s before you even mention the Pacers, who were a .500 team with Tyrese Haliburton in the lineup, who have the seventh pick in the draft incoming and young talent with room to grow.

The Magic were 5-19 to start the season and tanked the final five games. That means they went on a 29-24 run in the heart of the season. They’ll also be adding two lottery picks and can expect improvement from Paolo Banchero, Franz Wagner, Wendell Carter, Jalen Suggs and Markelle Fultz.

The Pistons shamelessly tanked their season away, but have Cade Cunningham and the fifth pick incoming with Jaden Ivey, Jalen Duren and more projected to improve. They could easily make a big jump.

Meanwhile, the Bulls “big three” played more minutes than any other trio in the league last year. They were healthy and individually played well. The Bulls likely won’t be a top-five defense next year. What if they can’t bring back Patrick Beverley?

In other words, their risk of downside exceeds their potential to improve. There is no Victor Wembanyama in next year’s draft — teams won’t be racing towards the bottom. I wouldn’t be surprised if the Bulls miss the Play-In Tournament if they keep things as is while the rest of the league improves around them.

@rtblues: Is building around Lavine as their No. 1 a realistic view of LaVine, and of championship level teams and their No. 1 players? Because that’s what’s we’ve been hearing a lot of lately. Not so sure if he’s “that guy”.

The sentiment here is well taken, but I think this is the wrong way to look at things. It’s the same perspective that led the previous regime to trade Jimmy Butler. There are maybe 10 players in the world good enough to lead a team to a championship and most of them have the help of another elite star. Devin Booker and Kevin Durant. LeBron James and Anthony Davis. Nikola Jokic and Jamal Murray. Stephen Curry and Draymond Green and Klay Thompson.

I think fans, media, analysts get a little too gung ho when it comes to rebuilds, draft picks and ‘the process’. There’s so much uncertainty with draft picks and young players in general and just doing it to do it can be a recipe for wandering in the middle for years to come. So when you have a guy who can be one of those players, even if not a top-10 player, it’s worth investing in building a team around him.

With all of that said, I do believe the Bulls have done their best to invest in LaVine. They moved future draft picks and operated above the cap to bring in talent. They addressed his weakness in defense by putting Caruso and Ball next to him. They addressed his playmaking weakness with Vucevic and DeRozan to help unburden him. While it worked for half of a season, it’s clear that it’s not going to work in the future.

Because the Bulls are so far away from putting that caliber of team together, they do need to be shopping him and everyone else on the roster. That’s not necessarily a knock on LaVine, it’s just the reality of the Bulls’ circumstance.

@DogsMkV: Do you think the Bulls can package something to get the Blazers No. 3 pick? Demar or Zach plus PWill or Coby with our 29 1st.

@BullsCentralYT: Realistically, can the Bulls actually trade up to get the #3 pick from Portland, and what would the trade package look like that would benefit both teams?

I like the idea here and with rumors out there, it’s always interesting to speculate. The Blazers are seeking win-now talent, specifically two-way wings, to flank Damian Lillard, and while the Bulls have win-now talent, I’m not sure they fit the mold of what the Blazers are looking for.

Zach LaVine is probably the closest thing, but if Mikal Bridges, Jaylen Brown, OG Anunoby, or Pascal Siakam are available, I’d imagine they would all be higher on Portland’s list. Alex Caruso could sweeten the deal, but that’s a lot of money to take on if you’re the Blazers.

You also have to consider who will be available to take third overall. I’d be much more inclined to make this kind of move for Scoot Henderson rather than Brandon Miller.

@charlieburr: I’m under the impression the Bulls’ initial plan was to wait until the 2024 offseason before any major facelifts to this roster (DeMar contract expiration, potential lonzo DPE, PWill new contract, better FA class, etc) What say you? Was this the plan all along since 2021 FA?

I’ve had this thought dating back to the DeMar DeRozan trade. With that top-10 protected pick going to San Antonio in 2025, a run through 2024 when DeRozan (’24), Nikola Vucevic (’23 pending re-signing), Lonzo Ball and Alex Caruso’s (both in ’25) contracts are up always made sense to me. Ride it out, then, if things fall apart due to old age, inability to fit everyone on the cap sheet, etc., you have the out in 2025 to be able to bottom out and keep your pick.

At that point, you have the ability to trade LaVine with only two years left on his deal, and a ton of cap room with only Dalen Terry currently under contract, but obviously extensions and future free agents change the calculus there.

With that said, if the Bulls are only a year ahead of schedule when it comes to the longer term plan of a rebuild/teardown/retool, they should probably just get ahead of it now and give themselves a chance to maximize the value of their trade chips to where they can actually develop down the line.

That’s it for today. Hope everyone has a nice and safe holiday weekend. If you’re looking into some more hoops, check out my NBA Draft Big Board and Database — an exclusive perk for CHGO Diehards!