Should the Minnesota Timberwolves pay the price to acquire Damian Lillard?

Minnesota Timberwolves President of Basketball Operations Gersson Rosas is known for big-game hunting.

Portland Trail Blazers superstar Damian Lillard is reportedly unhappy and it’s not impossible that he could request a trade.

Do the Wolves possess the assets to acquire Lillard? If yes … should they?

The possibility of the Minnesota Timberwolves acquiring Damian Lillard

Daryl Morey was Rosas’s mentor in Houston for over a decade. Morey, of course, was consistently churning his roster in an attempt to find a star. Once he had James Harden in the fold, the quest was to find a legitimate second star.

Rosas already had his superstar when he arrived in the Twin Cities. The initial pursuit and eventual acquisition of D’Angelo Russell gave him a second star, although maybe not quite to the caliber that would be ideal.

That’s led to ongoing speculation that Rosas may be willing to further churn his already-promising roster in order to land a second true superstar to Karl-Anthony Towns.

The best player who could be made available via trade is Portland’s Damian Lillard. It stands to reason that the Wolves would have interest on some level, although there isn’t a clear rumor connecting Minnesota and Portland.

Given Lillard’s level of discontent and Rosas’s desire to find another superstar, however, it’s not hard to connect the dots and try to parse if there could be something there.

What could the Minnesota Timberwolves offer to acquire Damian Lillard?

Let’s start by acknowledging what the Wolves have to offer in a trade.

Using our recently published trade value column as a guide, we know that the team’s best assets are, in some order, Towns, Anthony Edwards, Malik Beasley, Jaden McDaniels, Leandro Bolmaro, and future first-round draft picks.

Our own Dylan Jackson cobbled together three possible trade offers for the. All of them involve Anthony Edwards and multiple first-round picks going to Portland. One included Beasley, and one included McDaniels.

None had Towns in the mix, which makes sense. If the Wolves were to trade Towns in a deal for Lillard, one could fairly assume that it somewhat defeats the purpose on Minnesota’s end. Wouldn’t Rosas’ new roster simply be in a similar spot as Portland’s, albeit with the upside of Edwards presumably still in the backcourt along with Lillard?

Bleacher Report’s Zach Buckley also gave it a shot, and he put together the heftiest package yet:

This would include all of the Wolves’ top trade assets except Towns and McDaniels. It’s defensible, of course; Lillard is objectively a top-10 player, so it stands to reason that he’d require a haul.

Clearly, the Wolves have the assets to get a deal done. It’s simply a question of whether or not it’s a risk that Rosas should be willing to take.

The likely cost of the Minnesota Timberwolves acquiring Damian Lillard

If the Wolves completed the above trade that was initially suggested by B/R’s Buckley, they would have a roster centered on Towns, Lillard, and D’Angelo Russell. Robert Covington is a fine fourth-best player but only has a single year left on his contract. McDaniels would be on the team and would have to be relied upon as a true fourth or fifth option.

Minnesota would be forced to count on some of their young, affordable depth in bigger roles, including Naz Reid and Jaylen Nowell. A new backup point guard would need to be brought in, too.

Of course, a starting lineup of Lillard, Russell, Covington, McDaniels, and Towns would immediately be one of the best starting fives in the league, and regardless of proven bench depth, almost certainly a top-four team in the Western Conference.

However, there are two main questions that need to be addressed.

First, the fit of Russell and Lillard together in the backcourt. Defensively, it would be atrocious. Offensively, it would be dynamic, but with Lillard as the primary ball-handler, would there be enough shots for both Russell and Towns in addition to Dame?

Russell is great as an off-ball shooter and secondary creator, but his role would shift to a clear third option in the offense with Lillard in the fold.

Additionally, the Wolves would need both Covington and McDaniels to turn in above-average defensive performances if the lineup was going to stop opponents enough to make a deep playoff run. In this scenario, Josh Okogie and Jarrett Culver would still be on the roster and are second-line options as perimeter defenders as well.

The second question centers on Anthony Edwards. Six months ago, this trade would almost be a no-brainer. But Edwards improved in such a tangible way over the final months of his rookie year that the Wolves would need to pause long and hard before including Edwards in any trade.

Edwards still has three years on his rookie contract and, after future extensions, will surely be with the team much longer than Lillard, who has three years left on his max deal. Then again, if the Wolves knew they’d have a shot at a championship over those three years with a Towns + Lillard + Russell trio, then they’d make the deal in a heartbeat.

So, what’s the right answer? The Wolves would be wagering their future (Edwards, multiple draft picks) and their current fall-back trade assets (Beasley, Rubio, picks) that the new/present version of the roster would not only bring the team to the playoffs but genuinely threaten to win a championship.

This wouldn’t exactly be the Cleveland Cavaliers trading Andrew Wiggins for Kevin Love; Towns isn’t LeBron James, after all.

In other words, if Rosas were interested in a deal such as this, he would have to be 100 percent confident that a Lillard-Towns duo could lead the Wolves to the promised land. If that’s the case, then