The NBA offseason truly never ends, as there is always some sort of drama playing out right up to the start of the new season. Not only are James Harden and the Philadelphia 76ers proving that this year is no different, but Damian Lillard's situation with the Portland Trail Blazers continues to draw the attention of the league.
Lillard, one of the best pure scorers in the NBA right now, requested a trade from the Blazers early on in July at the start of free agency. Spending the first 11 years of his career with Portland, Lillard has been nothing but loyal to the franchise that drafted him sixth overall in 2012. However, the lack of success they've had these last few seasons has irked the All-NBA guard, hence why he wants to go somewhere else to compete for his first title.
Since the day he requested a trade, the Miami Heat have been the one team on Lillard's mind. The general consensus around the league is that the superstar will get his wish at some point in the coming months. This has not stopped other teams and stars from reaching out to Dame and the Blazers, though.
In fact, Boston Celtics All-Star Jayson Tatum was supposedly in contact with Lillard, expressing his team's interest in possibly striking a deal with Portland. The Celtics made the NBA Finals in 2022 and got within a game of getting back to the championship series just this past season. Tatum has his organization in championship mode right now, which is why the addition of Lillard could finally elevate them past the rest of the NBA.
The notion that Boston could land Dame this offseason is a little far-fetched now that they have acquired Kristaps Porzingis and extended Jaylen Brown, but there were some moments over the last several weeks in which the Celtics could have pursued the seven-time All-Star guard. Even now, there is still one scenario in which the two sides could get a deal done.
Here's a breakdown of what the Celtics could have offered the Trail Blazers throughout the offseason.
Damian Lillard's initial trade request
When Lillard first requested a trade would have been the best time for the Celtics to strike a deal this offseason. Quite honestly, this is likely around the time where Tatum first reached out to his fellow All-Star. Boston really did not make many moves in free agency, but this timeframe is when they had the most cap flexibility.
In this scenario, the Celtics would not have traded for Porzingis in June, Brown would not yet have his new contract extension, and Marcus Smart would still be a member of the team. Not to mention, Grant Williams was a restricted free agent Boston could have used in trade talks.
Following his trade request on July 1, the Celtics could have immediately put together an offer involving 2022-23 Sixth Man of the Year Malcolm Brogdon, recent first-round pick Payton Pritchard, veteran Danilo Gallinari and Williams in a sign-and-trade agreement. These four players listed above make a combined $45.7 million for the 2023-24 season and would would have matched Lillard's $45.6 million salary perfectly.
Boston also owns all of their first-round picks from 2024 through 2031, other than their first-round pick in 2028, so any combination of draft capital could have been attached in said trade with the Blazers.
It's also possible that the Celtics could have proposed a trade involving Smart and veteran big man Mike Muscala instead of offering Brogdon. A third team would have likely been involved in said scenario to take on Gallinari and Muscala's contracts. This is ultimately what happened with the Porzingis trade, as Washington currently has both veterans on their active roster. Of course, this scenario revolves around the idea of the Celtics not trading for Porzingis before Lillard originally asked out.
In exchange for Lillard, Portland would have received a starting point guard in either Brogdon or Smart, a young, defensive-minded forward who can play anywhere on the floor in Williams, and Pritchard would have been a young guard from Oregon who would provide even more backcourt depth. Whether or not this hypothetical package would have moved the needle for the Trail Blazers is a whole separate argument, as they would not be getting that much value in terms of the players they'd be receiving.
Already having Anfernee Simons and Scoot Henderson in their backcourt, the Blazers would not have an immediate need for Smart or Brogdon, especially if they are to begin rebuilding in the post-Lillard era. The same could be said for Pritchard, even though he is a young talent who would be the “hometown kid” for Portland. Williams is a really solid two-way player, but his upside is limited, and it is unlikely the Blazers would find value in him on a new four-year contract.
The start of free agency would have been the best time for the Celtics to come at the Trail Blazers with an offer for Lillard. Then again, it is hard to imagine they would have had what it takes to land him without including Brown in any deal.
Kristaps Porzingis acquisition and Jaylen Brown's extension
With Porzingis on their roster and after giving Brown a new five-year extension that could reach $304 million in total, the Celtics find themselves over the tax line for the 2023-24 season with over $170 million on their books. Any trade that they could potentially make would have to involve matching salaries or would need them to send out more in salaries than they are getting back. This would make pursuing Lillard and his $45.6 million contract for the upcoming year very hard.
Then again, the Celtics still have some options when it comes to trade discussions. Porzingis and Brown cannot be traded as a result of recently signing extensions with Boston, while Tatum is not up for discussion whatsoever. Not having Smart or Williams to leverage, this leaves the Celtics with Derrick White, Robert Williams III, Al Horford and Malcolm Brogdon as possible trade assets in a deal for Lillard.
Given that Tatum and Brown already initiate their team's offense with the ball in their hands, plus the hypothetical idea that they would be landing Lillard, the Celtics could realistically part ways with both Brogdon and White right now.
This would hurt their overall backcourt depth, and giving up White is not necessarily something they want to do after losing Smart this offseason. They would still have Pritchard as a backup guard option, though, and Lillard would assume the role of the starting point guard on this roster. As a result, Lillard would be an upgrade from White in the team's starting rotation.
In order to meet the kind of value the Blazers are wanting in return for Lillard, Boston would then need to likely trade either Al Horford or Robert Williams III. It's possible a third team would have to get involved at this point. As well as still having their draft assets mentioned before, the Celtics now also have an extra 2024 first-round pick via the Golden State Warriors that they can offer as a result of the three-team trade they made with the Wizards and Memphis Grizzlies.
The best possible trade package the Celtics could offer the Blazers right now involves White, Brogdon, Williams, two first-round picks in 2024 and a 2026 first-round pick. This is by far the best offer Portland will get from any team in the league at this point. All three players they would be receiving could then be flipped at the trade deadline or next offseason for even more future value.
From Boston's perspective, adding Lillard to a roster that already has Tatum, Brown, Horford and Porzingis undoubtedly makes them the favorite to win the 2024 NBA Finals. Then again, their bench would be made up of Pritchard, Sam Hauser, Oshae Brissett, Dalano Banton and whoever else they could sign to a minimum contract. Maybe in addition to Lillard, the Celtics could also acquire a smaller contract player like Keon Johnson or Jabari Walker from Portland.
While it is technically still possible that they could put together a realistic offer for Lillard, it's highly unlikely that the Celtics will be willing to part ways with all of their secondary assets. Not to mention, this hypothetical scenario would tie them down to nearly $500 million with Lillard, Porzingis, Brown and Tatum all under contract for at least the next three years.
Also, the bottom line is Portland's star wants to go to the Heat. While Tatum may have contacted Lillard this offseason, that mindset seems to be a thing of the past with training camp set to begin at the end of September.
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