The Portland Trail Blazers were rewarded for valuing Jrue Holiday as an asset in the Damian Lillard trade, as they subsequently moved Holiday to the Boston Celtics for Malcolm Brogdon, Robert Williams III and two first-round picks. That rounds up the return for Lillard (along with Nassir Little and Keon Johnson) to Deandre Ayton, Brogdon, Williams, Toumani Camara, three first-round picks and two pick swaps. That’s already a much better trade package than Miami, Lillard’s preferred choice, appeared to be offering.

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But the Blazers may have another potential move to make that could further improve the Lillard return. Brogdon, last season’s NBA Sixth Man of the Year, does not hold as much value on a rebuilding roster as he would elsewhere. At Monday’s Blazers media day, Portland general manager Joe Cronin complimented Brogdon and said the Blazers would be happy to keep him on the roster. Both Brogdon and Williams have physicals scheduled soon, and Cronin said the team needs veteran leaders like Brogdon around for its young roster.

However, Cronin also said, “We’re very open-minded to Malcolm,” to close his answer, indicating Brogdon’s status remains an open question. That wasn’t just lip service, league and agency sources told The Athletic. Their impression is that the Blazers are open to trade conversations about Brogdon, but don’t believe his situation is as time-sensitive as Holiday’s. If the right offer comes, they’re willing to discuss moving Brogdon, understanding he is an older player on a team unlikely to contend this season. But if that offer doesn’t come, the Blazers will take Brogdon into the season and ask him to aid the development of their younger guards while being productive himself.

The Blazers have a legitimate need for guard depth behind Scoot Henderson and Anfernee Simons; Skylar Mays, on a two-way contract, is the team’s next guard up after Brogdon. Still, Brogdon turns 31 in December, has injury question marks and is better suited on a roster in a contention window. Brogdon averaged about 15 points, four assists and four rebounds in 26 minutes per game last season, shooting a stellar 48 percent from the field, 44 percent from 3 and 87 percent from the line. He has two years left on his contract, making $22.5 million each season.

Over his seven NBA seasons, Brogdon has shown the ability to play as an on-ball creator or a secondary scorer. He averaged 19 points and six assists with a near 3-to-1 assist-to-turnover ratio in his three seasons with the Indiana Pacers. Last year in Boston, he shifted back and forth. Sometimes, he was the primary lead guard for bench units (often buoyed by Jayson Tatum, with whom Brogdon played about 60 percent of his minutes). Other times, he was the secondary creator next to Marcus Smart or Derrick White and took on a more aggressive scoring role.

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Brogdon tends to be deliberate player, and there are upsides and downsides to that. On some level, it allows him to overcome not being a crazy athlete, as he largely gets by on a mix of a powerful frame and skill level. Brogdon’s first option isn’t always to catch and shoot from 3, even though he’s excellent at it. Despite hitting 42.7 percent of his catch-and-shoot 3s last year, per Synergy, he only took 2.5 of them per game, which ranked 173rd among the 262 players to take at least 100 such attempts. Brogdon also averaged 4.43 dribbles per touch last year, according to the NBA’s stats site, which was the 27th most among the 263 players league-wide to log at least 1,000 minutes. That figure was also the highest on Boston by a full dribble per touch.

In addition, Brogdon’s injury history continues to worry teams looking to acquire him. It goes back to college, when Brogdon had a serious foot injury that concerned teams during the pre-draft process and ultimately caused him to fall into the second round. Late last season, he suffered a partial tendon tear in his right elbow, which he played through and elected to rehab without surgery this summer. He only played 36 games in the 2021-22 season due to an Achilles injury. In Feb. 2018, he partially tore a quad tendon. In 2019, he missed the end of the Milwaukee Bucks’ regular season and beginning of the playoffs with a plantar fascia tear. In March 2020, he tore a quad muscle. In total, Brogdon has played more than 68 games in a season just once and has only topped 60 in three out of seven years.

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Any team acquiring Brogdon is getting a win-now player who will have the ball in his hands often and is largely effective at constantly probing and attacking with straight-line drives to the rim. He’s not particularly bad on defense because of his strength, length and smarts, but he doesn’t add value there either, as his change-of-direction ability has slowed as he’s aged. As last season proved, he’s an awesome sixth man, which is probably his best role because it decreases his workload and keeps him healthier for longer. I’m not sure the leadership value he brings to the Blazers exceeds what he’d fetch in a trade.

Five teams can make the most compelling sense for acquiring Brogdon, but a few other teams are worth noting. Note that many of these teams would find it easier to create a trade package if Portland keeps Brogdon on its roster past Dec. 15, when most offseason signings become eligible to be traded.

• The Minnesota Timberwolves certainly could use another strong, offensively minded backcourt member alongside Mike Conley and Anthony Edwards, but the Wolves don’t have an ideal mechanism with which to match salaries.
• The Denver Nuggets similarly fit this billing. Denver doesn’t have the trade-matching salaries that make sense, even though they could be on the lookout for backcourt depth after losing Bruce Brown in free agency.
• Unless the Brooklyn Nets are interested in a straight Spencer Dinwiddie swap — which I don’t think makes a lot of sense — they’re in a similar position to the Wolves.
• The Cleveland Cavaliers could use another backcourt creator to use with Donovan Mitchell and/or Darius Garland, especially one that can shoot. But they also do not have an ideal salary match to make the trade math work unless both sides are willing to accept a package of Isaac Okoro, Dean Wade and Ricky Rubio. Does Portland like Okoro enough to give him real minutes and potentially pay him this offseason, in addition to taking on multiple years of both Wade’s and Rubio’s contracts? That feels like a no-go.
• The New Orleans Pelicans are in a similar boat. Brogdon would be an interesting piece, but the Pels don’t have a matching salary to include unless they’re willing to move Jonas Valančiūnas. Given Zion Williamson’s eternal health concerns, Valančiūnas should be a required player for the Pelicans to start the season.
• The Chicago Bulls are almost certainly on the lookout for more offensively minded guard depth, and Brogdon fits the billing. The issue is that Lonzo Ball is the only contract the Bulls currently have available to trade to match salary, and given his injury uncertainty, they may have to give up a first-round pick to get out from under that money on its own. I don’t believe Chicago executive vice president of basketball operations Artūras Karnišovas would do that, especially after spending the summer retaining and acquiring players like Jevon Carter, Ayo Dosunmu and Coby White.
• The Miami Heat make sense for Brogdon, but we can assume the Portland and Miami front offices aren’t exactly enthused to work together right now.

So what is Brogdon’s immediate market if Portland looks to trade him?

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• Rockets acquire Brogdon; Blazers acquire Kevin Porter Jr., Jae’Sean Tate and four second-rounders

Porter’s NBA future is unclear in the wake of his charges of felony assault and strangulation due to an alleged attack on his girlfriend. Rockets general manager Rafael Stone said Monday that he informed Porter’s representation that, “He could not be part of the Houston Rockets,” and that he will not be at training camp.

Basketball-wise, Porter’s unique, largely non-guaranteed contract only has $1 million locked in beyond this season. It can act as an expiring deal that the Blazers could acquire and then immediately cut, since an additional $2 million of his 2024-25 salary becomes guaranteed on this season’s opening night. There is obviously a moral question about whether NBA teams should use Porter’s deal as a mechanism to ostensibly improve their roster, and Portland would need to decide how comfortable it is having Porter’s name on the roster, even if just briefly before releasing him.

The get for Portland would be Tate and draft capital. Tate missed a portion of last season, but he’s a tough, aggressive defensive player who is physical, rebounds well, can pass and makes all of the little extra plays on the court to make life easier for his teammates. He would potentially provide the leadership Cronin wants around his young players, or yet another asset for Portland to move elsewhere, as a number of contending teams would be interested in his services. My favorite of those deals involves the Memphis Grizzlies using the trade exception it received in Houston’s Dillon Brooks sign-and-trade to take in Tate for draft capital. Additionally, the Celtics could do something along the lines of Payton Pritchard, a sign-and-traded Blake Griffin and a second-rounder for Tate.

Backcourt depth was a significant issue for the Rockets last season. They ended up playing Daishen Nix, Josh Christopher and TyTy Washington Jr. more than 2,100 minutes combined. They took the first step toward rectifying that by signing Fred VanVleet, but will also lose Porter’s 2,000 minutes. Acquiring Brogdon would substantially raise the floor of the Rockets’ performance in a season in which the front office needs to see serious on-court growth. The combination of VanVleet and Brogdon would allow the Rockets to always have a professional decision-maker handling the ball and would provide a more competitive environment for young players like Jalen Green and Amen Thompson. The Rockets have 11 second-rounders that can be moved in a trade, so they aren’t exactly depleting a scarce resource in this potential deal. It’s also worth noting that while new Rockets head coach Ime Udoka never coached Brogdon in a regular-season game, he held that position in Boston when the Celtics acquired Brogdon last summer.

This one ticks a lot of boxes.

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• Clippers acquire Brogdon; Blazers acquire Marcus Morris Sr., Amir Coffey, Brandon Boston Jr., a 2027 first-round pick swap and two second rounders

The Clippers tried to acquire Brogdon earlier this summer in an early iteration of the trade that saw the Celtics get Kristaps Porziņģis. That deal fell apart due to an issue with Brogdon’s medicals, which was complicated by Porziņģis needing to make an imminent decision on his 2023-24 player option.

As I wrote recently, the Clippers need to do something to bolster their roster, particularly in the backcourt. This deal accomplishes that, even if Brogdon is not as strong an upgrade as Jrue Holiday would have been. Brogdon’s ability to play on the ball and hit shots from distance would benefit the Clippers. They could play him at point with someone like Norman Powell off the bench, or slot him in next to Russell Westbrook as a starter given his size. While I think it would behoove the Clippers to acquire someone who makes decisions a bit more quickly than Brogdon as a passer, his deliberate style fits with the kind of players the Clippers’ front office has prioritized recently.

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Though Brogdon has trade value, it’s hard to pinpoint a team that would actually part with a first-round pick for him. The contracts of Morris, Coffey and Boston all expire after this season, though Boston could fit Portland’s timeline as an intriguing, scoring wing. A 2027 first-round pick swap theoretically gives the Blazers enough time to turn things around to the point they are able to exercise the exchange. The Clippers have four second-rounders available to trade.

The Clippers’ original deal with Boston involved the No. 30 overall pick in June’s draft, which LA used on Missouri forward Kobe Brown. The Blazers could persuade the Clippers to part with Brown in a similar deal, but considering LA was the team that originally raised the medical concern with Brogdon, it may not be as inclined to part with that much draft capital this time around. Yet it’s also possible that removing the rush of Porzingis’ player option decision give the Clippers time to ascertain a more robust understanding of Brogdon’s medicals. Rather than Brown — or Bones Hyland, who also fulfills Portland’s need for a guard — I’ve gone with a pick swap in this offer. In the spring, the Clippers completed what amounted to a pick swap deal to acquire Eric Gordon from the Rockets, so they are well-versed in the idea.

I’m not sure this tops a potential Rockets offer, though, depending on whether Portland can survey the market for Tate ahead of time and find something else of value. Including Brown would top it, but I’m skeptical the Clippers do that.

• Magic acquire Brogdon; Blazers acquire Jonathan Isaac, Cole Anthony and two second-rounders

The Magic want to take a leap this season, and they have reason to believe they can. After starting 5-20 last season, Orlando finished 29-28 in its final 57 games, a period that mostly dovetailed with Markelle Fultz’s return from injury. Franz Wagner, Paolo Banchero and Wendell Carter form a terrific young frontcourt core, but the Magic need more consistent play in the backcourt beyond Fultz and Gary Harris. Much as I love him, I’m skeptical that Joe Ingles, 36, has much juice left in his legs. Jalen Suggs and Anthony Black are intriguing prospects, but both are raw in their offensive development. Brogdon would certainly help, and as as big-bodied guard with length, he fits the mold team president Jeff Weltman and company tend to look for with their roster.

The only player Weltman has drafted during his time in Orlando who doesn’t fit that profile is Anthony, an undersized point guard who has developed into a solid player at just 23 years old. He had a positive true shooting percentage for a point guard last season at 57.4 percent, is an awesome rebounder and has become much more careful with the ball. But the Magic have consistently acquired players to play over him –Black in the 2023 draft, Suggs in 2021 and Fultz, who they’ve prioritized developing since trading for him in 2019. Anthony should be a good backup point guard for a long time, but he only has one year remaining on his rookie deal before he hits restricted free agency. Will the Magic want to pay him? If the Magic see both as one-year players with the organization, Brogdon is an upgrade for this season on Anthony.

Isaac is included for salary-matching purposes. The promise of Isaac’s elite defensive upside is tough to buy into at this point. He’s played in just 14 games since the calendar turned to 2020, and 11 of those came in a return bid last season that started in January, but ended in February when he tore an adductor muscle and was ruled out for the rest of the season. His contract is partially guaranteed for $7.6 million until Jan. 10, meaning the Blazers could either cut him and save a lot of money, look to trade him to a team looking to avoid the luxury tax or see if he has any juice left in his legs before that guarantee date. The Magic would have to up his guarantee to about $12.5 million for a deal to work, but that still results in quite a bit of potential savings.

Regardless, the idea for the Magic is to bolster their backcourt with another player who can knock down shots on a roster that needs it. Brogdon is one of the better players they’d be able to acquire if they decide to target someone who can help them this year, as opposed to using the Isaac deal to accrue another future asset in a salary dump. The Blazers get a couple of picks, potentially get to reuse Isaac’s deal before January and try out Anthony as a potential backcourt option behind Henderson and Simons.

• 76ers acquire Brogdon; Blazers acquire P.J. Tucker, Furkan Korkmaz, Danuel House and four second-rounders

I don’t think this deal gets it done for Portland unless the bottom completely falls out of Brogdon’s market. But I list it here for two reasons.

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First, Brogdon would be substantial insurance for whatever happens with James Harden. Getting Brogdon might allow the Sixers to play out  the Harden situation even longer if the team gets off to a good start with a backcourt of Brogdon, Tyrese Maxey and De’Anthony Melton surrounding Joel Embiid.

The second reason? It would be hilarious to see 76ers fans reckon with Brogdon and Embiid suiting up together after their Rookie of the Year battle in 2017.

But the Blazers should get better offers than this. I don’t think Philadelphia should open one hole to plug another by including Melton in a trade for Brogdon. Additionally, the 76ers have clearly been trying to maximize their cap space next summer to pivot in their roster build around Embiid. If they need to find a second star, they have a relatively low cap hold on Maxey, as well as the expiring contracts of Tobias Harris, Melton, Korkmaz and House. Adding Brogdon would cut into that flexibility. Plus, because they are already out two first-round picks in the future, the 76ers can’t afford to move another for a player like Brogdon who would help, but may not significantly move the needle.

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• Raptors acquire Brogdon; Blazers acquire Chris Boucher, Otto Porter Jr., Malachi Flynn and three second-rounders

The Raptors could use another guard in the backcourt, and Brogdon fits. The team was seemingly engaged with the Blazers on a Lillard deal, although team president Masai Ujiri tends to prioritize upside when building his rosters. I don’t think the Raptors would give up a first-rounder for Brogdon, especially because they’re already out one following the trade for Jakob Poeltl last February. I don’t think the Raptors would offer much more than this, but if they could do a Brogdon deal on the margins, that might make some sense.

But I think this is the kind of deal Portland would pass on for now. Boucher and Porter don’t have all that much rerouting value on the trade market. Flynn doesn’t have a ton of value league-wide, though he’s at least an interesting throw-in for a rebuilding team that needs guard depth. He’s had flashes of strong play and possesses the kind of toughness and skill level that might appeal to Portland. But Flynn also never got his feet underneath him under Nick Nurse and thus is now on what amounts to a one-year “prove it” contract before hitting restricted free agency.

It’s worth throwing Toronto into the Brogdon mix due to its roster needs, but I don’t see a great match here, barring a strange choice like including Precious Achiuwa in the talks to avoid paying him in restricted free agency.

Final Verdict

The Houston deal makes the most sense to me. Portland would get a solid mix of draft capital and potential veteran leadership, plus a solid rotation player with rerouting trade value in Tate. They would also be the likely catalyst in any deal for Brogdon that occurs before opening night, given the time crunch they’re under to make something of Porter Jr’s deal before more of it becomes guaranteed.

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The Rockets have the right mix of time pressure for this deal and a front office needing show real growth in terms of wins and losses. Throw in the (albeit brief) Udoka and Brogdon connection in Boston, and it seems like the right blend of a deal for everyone involved.

(Top photo of Malcolm Brogdon and Cole Anthony: Brian Fluharty / Getty Images)