Five questions about the Timberwolves' future that need answers soon

Imagine the Timberwolves are a used boat that you aren't sure you really like, but someone is offering to sell it to you just in time for summer with the promise that you don't have to make any payments on it for one year.

That's the way I'm choosing to make simpler sense of a complicated offseason dilemma for the Wolves that ultimately comes down to questions of being proactive vs. reactive, how good they think they can be next season and what they ultimately think of their core.

Bobby Marks, an NBA insider for ESPN, joined me on Thursday's Daily Delivery podcast to break down some of the biggest questions facing Minnesota this summer.

I didn't enlighten him with my boat analogy — that's just for you, dear readers — but he did add a lot of context about what I deem the five questions the Wolves must answer about their future.

How will the new collective bargaining agreement impact the Wolves? The league and players ensured labor peace through almost the rest of this decade with a new CBA earlier this year.

The upshot of it, Marks said, is that teams essentially have this offseason to "get their finances in order" but that by next offseason it will be difficult to add pieces to a top-heavy roster and more difficult to construct megadeals because of various rules for teams above the salary cap line.

Marks said the massive trade the Wolves made for Rudy Gobert, for instance, would be much more difficult a year from now. He also wondered, "If Minnesota would have known what these CBA rules were going to be, would they still have made this trade?"

All of that will give the Wolves less flexibility a year from now. They need to decide this summer how much they like their roster — just like you need to decide how much you like that boat — because a year from now the bills are going to come due.

Can the Wolves carry three max contract players? Marks pointed out that Denver is the only team in the league that currently has three players on maximum contracts with Nikola Jokic, Jamal Murray and Michael Porter Jr.

By next year, the Wolves could join them assuming Karl-Anthony Towns (whose max deal kicks in next year) isn't traded and Anthony Edwards signs a max extension this offseason that begins in 2024.

It has worked in Denver — not coincidentally the former employer of current Wolves personnel boss Tim Connelly — because of strong roster management and the ascent of Jokic, a two-time MVP who is two wins short of his first NBA title.

"You can do it," Marks said of having three max players, "but you better make sure everything around the three players is very good."

What is the ceiling of the 2023-24 Wolves? The offseason dilemma for the Wolves would be diminished if they had the season last year many expected — a top-four finish in the West and advancing at least to the second round of the playoffs. Instead, they went 42-40 and were bounced quickly from the playoffs as the No. 8 seed.

If the Wolves think they can compete by running it back before all the big contracts kick in, they will likely go for it and sort out the tough questions of roster construction a year from now. Marks is optimistic that Gobert will have a better season in Year 2 and isn't ready to label last summer's blockbuster a failure.

But if the Wolves don't think they can compete? This offseason is the time to explore a reboot, and a Towns trade is the most likely major piece of that.

"If you ever got to a decision where Karl was the guy you needed to move to break up the contract and balance your roster," Marks said, "and you figure that Anthony is our guy that we're going to build around, this is kind of your window to go out and do it."

What about the point guard? Mike Conley Jr. proved to be a good fit and one of their best playoff performers after being acquired at the trade deadline last year. But he's also going to turn 36 before next season starts, and he's in the final year of his contract.

If the Wolves don't reshape their team before this time next year, they'll be staring at a roster with three max contracts, another big one with a likely lucrative Jaden McDaniels extension (figure maybe $20 million a year) and no starting point guard.

The Wolves do have their first-round pick in 2024, but if they have the kind of season they hope to have that will likely be late in the round. And the Gobert trade plus other salary constraints would leave them limited.

"You have one of the top wings in the NBA on your roster, and there's still a huge upside to him. You have a very tradeable player in Karl if you ever wanted to pivot. You have one of the better defenders in the league in McDaniels," Marks said of the team's roster in general. "The downside is that you've boxed yourself into a corner a little bit."

Is it worth trading into the first round of this month's draft? The Wolves don't have a first-round pick in the draft later this month, of course, and their second-rounder is way down at No. 53. Some have suggested a Towns trade this offseason could be built around Portland's No. 3 pick and other players, which would allow the Wolves to perhaps balance their roster (and books) while acquiring point guard Scoot Henderson (who would need to be drafted by Portland and traded next month because of Towns' contract).

Marks said he understands the trade chatter but that, "I'm not ready to start doing nine different trade scenarios on Karl-Anthony Towns." When asked if he thinks the Wolves should try to get into the first round of this year's draft by different means, Marks said he doesn't think so because "it's hard to get into the first round unless you're willing to sacrifice something of value."

In the end, this offseason will hinge on how the Wolves feel about Towns and whether they think they can afford to be patient knowing what looms ahead in 2024.

The waters look choppy, but the boat is yours if you want it.