The 2024-25 campaign has been a mixed bag for Portland. Currently holding a 21-29 record, the Blazers have shown promise but have mostly been hampered by inconsistency. Despite being in a rebuilding phase, they’ve managed to stay competitive, positioning them for a projected No. 7 pick in the upcoming draft. That's not quite high enough to secure a game-changing prospect. This situation signals that it may be time for the franchise to move on from some veterans to both improve their draft position and acquire promising young assets.

Veterans on the Move: Grant and Simons

Portland has two standout veterans who, despite their undeniable talent, no longer align with the team’s current trajectory. Jerami Grant is a versatile power forward known for his defensive prowess, scoring ability, and three-point shooting. However, he has struggled to thrive alongside a youthful, developing roster. A fresh start on a contending team could reignite his performance. He certainly fits the mold of a player any championship contender would covet. However, his hefty contract—$34 million annually over the next three seasons—presents a significant financial commitment.

Blazers Jerami Grant with question marks everywhere.

The other one is Anfernee Simons. He is just 25 years old and a seven-year NBA veteran. Right now, Simon finds himself in a crowded backcourt. Sure, he’s a natural scorer capable of dropping 20 points with ease. That said, Portland’s surplus of shooting guards and his less-than-successful stint at point guard have made his role less clear. Simons’ contract, paying him $26 million this season and $27.5 million next, adds to the complexity of any potential trade.

Here we will discuss the player who's part of the Portland Trail Blazers' dream scenario for the 2025 NBA trade deadline.

Moving Jerami Grant

Should the Blazers decide to part ways with Grant midway through the second year of his five-year, $160 million extension, they’d be trading him at what might be his lowest market value to date. Grant is shooting under 39 percent from the field and has significantly regressed on defense compared to his prime seasons. At 30 years old, his career trajectory appears to be on the decline. His age makes him much more of a likely tradable player compared to Simons.

Yes, offloading his contract to shed salary is one reason to explore a trade. However, there’s an even more pressing concern: Grant’s presence could hinder Portland’s rebuilding efforts. His hefty contract clogs up cap space, and his role in the lineup could stifle the development of younger players. The longer Grant remains on the roster, the harder it becomes to prioritize the growth of the Blazers' emerging core. Portland must really find a way to move his contract without inheriting an equally burdensome or extended deal. They should see the trade deadline as a massive opportunity to do so.

Targeting Khris Middleton

Khris Middleton surrounded by question marks with a Cavs/Bucks-themed BG.

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The Houston Rockets invested heavily into Fred VanVleet during the 2023 offseason. Houston gave the point guard a three-year, $128 million deal in a move that was meant to turn the Rockets from a rebuilding team into a championship contending one. The signing did just that, as the Rockets finished the 2024-25 regular season as the two-seed in a stacked Western Conference. VanVleet was the veteran presence and 3-point shooter that the team desperately needed, and he still might have a role with the Rockets going forward. Houston has a team option on his contract for next year, and they very well may pick it up. The Wichita State product reportedly wants to stay in Houston, but the point guard would be set to make over $44 million next season under his current contract. The Rockets and their guard recently pushed back the deadline on Houston's decision with VanVleet, and although reports suggest that they are interested in writing up a new, long-term deal, it isn't necessarily a guarantee that VanVleet will be playing for Houston next year. The Rockets blew him away with an offer he couldn't refuse back in 2023, and another team could so the same when/if he hits the open market this offseason. If VanVleet does become an unrestricted free agent, which teams outside of Houston would make the most sense for him to sign with? 1. Orlando Magic Jalen Suggs and Franz Wagner recently signed big deals with the Orlando Magic, and Paolo Banchero will be getting a mega contract extension here soon. Because of that, the Magic no longer have money to blow like they have had in recent years. That will make a deal for another big ticket free agent hard to pull off, especially considering the team signed Kentavious Caldwell-Pope last year. If Orlando can make the money work, though, then Fred VanVleet would be a great fit with the Magic. The Magic finished dead last in 3-point shooting this season, and VanVleet has made at least 2.5 deep balls per game in every season since 2018-19. VanVleet can hit shots form behind the arc off of the bounce or in catch-and-shoot situations. The Rockets were heavily reliant on his shooting expertise, so the guard would have plenty of familiarity getting up deep shots with high volume if he signed with the Magic. While undersized, VanVleet is a pesky defender, so he'd fit right in with a Magic team that has one of the best defensive units in the league. VanVleet could play alongside Suggs and give opposing teams fits. Ultimately, though, the Magic just need more shooting to get to the next level, and VanVleet is arguably the best shooter who could be available on the open market this offseason. 2. Brooklyn Nets A more realistic option for a VanVleet destination would be the Brooklyn Nets. The Nets are set up to have the most cap space this offseason, and they have a major need at point guard. With D'Angelo Russell and De'Anthony Melton hitting free agency this offseason, the Nets don't have a true point guard under contract for next season. Brooklyn needs to spend big this offseason, and they'd be smart to offer VanVleet a contract big enough that he'd have no choice but to leave Houston. VanVleet averaged 14.1 points per game last season, which was his lowest mark since 2018-19. He is trending the wrong way, but he still has enough left in the tank to give the Nets a few good seasons. 3. Portland Trail Blazers In the same way that the Rockets were looking to take the next step in 2023, the Portland Trail Blazers could use VanVleet's presence to get over the hump. The Trail Blazers have plenty of big man depth, as centers Deandre Ayton, Donovan Clingan, Robert Williams, and Duop Death are all under contract next season. Portland also has a lot of wing depth. Deni Advija started to look like a star late this past season, Toumani Camara is an elite defender, Shaedon Sharpe is a freakish athlete, and Jerami Grant is a proven scorer. The team is thinner in the backcourt, though. Anfernee Simons is a solid scorer, but Scoot Henderson has looked like a fringe draft bust since being drafted third overall. Portland shouldn't give up on Henderson completely, but there wouldn't be any harm in signing another guard. Like the Magic, the Blazers were one of the worst 3-point shooting teams in the NBA. VanVleet would improve that weakness, and in a stacked Western Conference, Portland needs all of the help they can get if they are to compete for a playoff spot.
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A trade to ship Grant out and bring in Khris Middleton would be excellent for the Blazers. This kind of deal would offer Portland a proven veteran with championship experience. Recall that Middleton was instrumental in the Milwaukee Bucks’ 2021 NBA title run. His ability to thrive under pressure, coupled with his versatile scoring and playmaking, makes him an ideal fit alongside Portland’s young stars. Unlike Grant, who flourishes in isolation and as a secondary scoring option, Middleton’s adaptable skill set allows him to facilitate offense. He can space the floor with his shooting and lead in clutch moments.

Financial Considerations and Team Dynamics

Yes, both Grant and Middleton carry substantial contracts. However, Middleton’s deal provides more long-term financial flexibility. Grant’s current deal represents a long-term cap hit that could limit Portland’s ability to pursue other key acquisitions. Middleton’s contract, though still significant, givesthe Blazers a chance to reassess their cap situation sooner and pivot as needed. This flexibility is crucial as Portland builds around promising talents like Scoot Henderson and Shaedon Sharpe.

Why Milwaukee Might Consider It

From Milwaukee’s perspective, acquiring Jerami Grant could inject new life into their lineup. Grant’s defensive versatility and scoring ability would complement Giannis Antetokounmpo and Damian Lillard. At 30, Grant is younger and more athletic than Middleton. He offers the Bucks a chance to rejuvenate their roster while staying firmly in the championship hunt. With the Eastern Conference growing increasingly competitive, this trade could be the boost Milwaukee needs to sustain its playoff ambitions.

Seizing the Moment

As the 2025 NBA trade deadline draws near, the Blazers have a unique opportunity to reshape their future. Trading Jerami Grant for Khris Middleton is a bold, strategic move that reflects a desire to break free from mediocrity and aim higher. While it’s a gamble, the potential payoff could be monumental, bringing Portland closer to the championship aspirations that have long eluded them. For a franchise and fanbase yearning for a fresh start, this dream scenario could be the defining moment they’ve been waiting for.

For the Blazers, standing still is no longer an option. This trade deadline represents more than just an opportunity—it’s a statement. Moving Jerami Grant for Khris Middleton isn’t just about swapping players; it’s about signaling to the league and their loyal fans that Portland is ready to embrace change, take risks, and pursue greatness. The pieces are on the board, and the time to make a decisive move is now. The future of the franchise could very well depend on it.