Despite improving their roster from last season and cementing their star backcourt in place with extensions for Damian Lillard and CJ McCollum, the Portland Trail Blazers have the highest payroll in the NBA and are bound for luxury tax hell in the coming months unless some changes are made. Following an unconvincing 3-4 start to the regular season, ESPN's Brian Windhorst didn't take long to land on Danilo Gallinari as a potential trade target, while suggesting the Blazers will be active in the trade market, likely trying to shed some of that extra expiring salary.

“When I’ve talked to executives out there seeing this [high a payroll], they believe that the Blazers are going to be active in the trade market as the season goes on,” said Windhorst on The Jump. ”They have the pieces that are required for a trade, they have a couple of expiring contracts in Hassan Whiteside and Kent Bazemore. They have a couple of young players, maybe Anfernee Simons. They have picks, there's a couple of guys — but what they really need is forwards… They lost Al-Farouq Aminu, they lost [Moe] Harkless, watch Danilo Gallinari.”

The Blazers have $145 million committed to their players this season, well past the $138.9 million apron for 2018-19. While they have been long rumored to bring home Kevin Love from the Cleveland Cavaliers, trying their hand at Gallo could be the right answer for them this season.

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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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Gallinari is making $22.6 million in the last year of his contract before becoming a free agent in 2020, which comes much cheaper than the $28.9 million that is owed to Love as the first of a four-year, $120 million max extension he signed with the Cleveland Cavaliers at the beginning of last season.

Gallo, who was traded to the Oklahoma City Thunder as part of the Paul George trade with the Los Angeles Clippers, could give the Blazers the right kind of floor spacing without gobbling up much room in the paint, where Nurkic likes to operate.

His perimeter shooting can open up the floor for Lillard and McCollum, giving them much better options to rely on with their backcourt assault and rounding up a part of the Blazers game that has been lacking the past few years since LaMarcus Aldridge left for San Antonio.