The Portland Trail Blazers front office is obviously not satisfied with their poor luck in this year’s draft lottery. They finished tied with the third-worst record in the league and ended up with the No. 7 pick. Meanwhile, the Houston Rockets finished just short of a Play-In Tournament spot this season but ended up with the third pick in the draft via the Brooklyn Nets.

The teams seem to have mutual interests, as the Blazers are seeking coveted draft prospects to accelerate their rebuild, and the Rockets are trying to add pieces to compete in the playoffs.

How desperate is Portland for a higher pick?

But in an uncertain draft, how big of a difference is there between the No. 3 pick and the No. 7 pick? It could be significant in Portland’s eyes. Rumors are circulating that Portland is reportedly high on Donovan Clingan. The only problem is that it seems like every other team picking in the lottery is also high on him, regardless of his positional fit.

A few months ago, it seemed very realistic for Clingan to be available at pick No. 7, but it’s become increasingly unlikely based on recent mock drafts. He is now a top-five pick in most mock drafts, and The Ringers’ Kevin O’Connor believes that Clingan will be the No. 3 pick in the draft. Whether it be Clingan that the Blazers have their eyes on or someone else, the assets going to Houston in this mock trade are very valuable. Portland needs to have a lot of faith in whoever they pick at No. 3 for this trade to be worth it.

O’Connor and J. Kyle Mann proposed a theoretical trade on a recent episode of their “NBA Draft Show” podcast based on the Blazers’ potential interest in trading up in this year’s NBA Draft.

Here’s what the trade looks like:

Blazers receive No. 3 pick from Rockets in brainstormed proposal

For Houston, Anfernee Simons could be an intriguing addition and give them some long-term insurance for the 30-year-old Fred VanVleet, who has two years remaining on his contract with a team option for the 2025-26 season. That team option is worth $44.9 million, so having Simons in the mix could incentivize the Rockets to let VanVleet and his massive contract walk in free agency. At 25, Simons fits their timeline better alongside their young core of Amen Thompson, Jabari Smith Jr., Jalen Green, and Alperen Sengun, among others.

This deal was not a finalized trade proposal, as O’Connor and Mann were brainstorming possibilities for the Blazers to trade up. As it stands, this trade wouldn’t work financially. The Blazers would have to receive a player in return for this trade to work, and there are a few possibilities – If Houston doesn’t want to give up someone who is a core part of their rotation, Portland may accept someone like Steven Adams or Jock Landale in this trade. However, if the Blazers feel they have some leverage, they could ask for someone like Dillon Brooks instead.

No matter which player the Blazers get in return, the biggest prize is going to be the No. 3 pick in this year’s draft; this begs the question, are all the valuable assets the Blazers are giving up in this deal worth having the No. 3 pick for the second consecutive year?

Are the Blazers giving up too much?

If the Trail Blazers were to make this deal, they would certainly be criticized by everyone besides Rockets fans. Two lottery picks and the team’s best scorer for the No. 3 overall pick would undoubtedly leave some fans baffled, especially considering it’s a notoriously weak draft with no clear-cut tiers of prospects to differentiate the No. 3 and No. 7 pick like in typical drafts.

Houston’s addition of Simons is key to their likely acceptance of this trade with little to no negotiation. Despite the potential for a crowded backcourt with VanVleet, Green, and Simons, the offensive boost could be worth it as they look to make a playoff push. Meanwhile, Portland only agrees to this trade if they are confident that someone they like will be available at No. 3. Other than Clingan, potential candidates include Zaccharie Risacher, Alex Sarr, and Matas Buzelis.

Bold trades like this typically go down in league history on extreme ends of the spectrum – either colossal failures or massive successes. The risk outweighs the reward for Portland, particularly in a weak draft class.

The Blazers shouldn’t accept this brainstormed deal. However, the possibility of having another top-three pick on the team and the mutual interests of these teams make this trade seem more reasonable.

Trail Blazers trade grade: C+