Trail Blazers accumulate picks, address size issue while sending Jrue Holiday to Boston Celtics

The Portland Trail Blazers still probably don’t rate as a playoff team in 2023-24, but the franchise is moving forward from the Damian Lillard trade with a promising, athletic, youthful roster and a healthy heaping of draft capital to play with.

On Sunday, the Blazers traded All-Star guard Jrue Holiday to the Boston Celtics for center Robert Williams, a high-end defender and veteran point guard Malcolm Brogdon, Golden State’s 2024 first-round pick (top four protected) and Boston’s 2029 first-round pick.

That deal came days after the Blazers, in a three-team trade, sent Lillard to the Celtics for Holiday, guard Grayson Allen, the Bucks’ first-round pick in 2029 and pick swaps in 2028 and 2030. The Blazers in the exchange sent Jusuf Nurkic, Nassir Little and Keon Johnson to the Suns for center Deandre Ayton and forward Toumani Camara (a second-round pick last spring) while Phoenix also received Allen.

Confused? Understandable.

To clarify, Blazers general manager Joe Cronin hauled in the following: Ayton, Williams, Brogdon, Camara, three first-round picks and two pick swaps.

Gone are Lillard, Nurkic, Little and Johnson.

It will never fully be known if the Blazers ended their trading spree with more assets than they could have gathered had they fully engaged in trade talks with Miami, Lillard’s preferred destination. Those talks revolved around just Lillard going to Miami whereas the totality of player movement ultimately included Nurkic, Little and Johnson being shipped to the Suns.

The Ayton component, according to NBA sources, had been discussed separately from a Lillard deal. But the Suns sought to accumulate depth for Ayton making adding a third team necessary to finalizing a deal.

That all said, while the Blazers all but ignored Miami, the Heat failed to step forward with an initial offer that Portland deemed worthy of kicking off negotiations.

In the end, the Blazers and Lillard both came out of this sordid mess very well while the Heat, who last season reached the NBA Finals, watched Eastern Conference rivals Milwaukee and Boston make significant upgrades.

For the first time in Lillard’s career, he has a chance to contend for an NBA title while playing with Giannis Antetokounmpo while the Blazers successfully reset the franchise with a strong enough combination of young talent and draft picks moving forward.

So, where does all of this leave the Blazers heading into this season? Tough to say.

The Western Conference is stacked with quality teams leaving the Blazers likely ranked in the bottom five entering the season.

While the team’s talent level is strong, overall depth remains an issue.

Here is a look at a proposed 10-man rotation entering training camp, which starts Tuesday in Santa Barbara, Calif.:

Point guard: Anfernee Simons or Scoot Henderson, Malcolm Brogdon.

Shooting guard: Simons, if Henderson starts at point guard, Shaedon Sharpe and Matisse Thybulle.

Small forward: Thybulle or Sharpe.

Power forward: Jerami Grant, Kris Murray, Jabari Walker.

Center: Deandre Ayton, Robert Williams.

This group won’t be short on athleticism. Simons, Henderson, Sharpe, Grant, Ayton and Williams will be a handful for most teams.

First and foremost, in order for the Blazers to realistically challenge for a playoff spot they must hit a home run with Ayton.

The No. 1 overall pick in 2018 flashed brilliance during his five seasons in Phoenix but proved inconsistent enough for the Suns to not want him in town for their upcoming championship quest.

The 6-foot-11 Ayton has the ability to become a dominant force and is far more athletic than Nurkic and better around the basket. It will be up to coach Chauncey Billups to help Ayton turn his career around.

Adding the 6-9 Williams, a plus-defender, gives the team a legitimate backup center who could see some minutes at power forward. The major knock on Williams is that he has struggled to stay healthy. He missed 47 games last season.

Henderson, Simons and Sharpe are all high-flyers. But what could ultimately cost the Blazers is a lack of height in the backcourt and few veterans to turn to.

Sound familiar?

The Blazers exited last season pointing to a lack of length and veteran depth as major problems that needed to be addressed.

The tallest player among the small forward candidates and guards is the 6-5 Thybulle. Sharpe is just under 6-5, Simons is 6-3 and Henderson, 6-2.

A lot must fall into place in order for Portland to find success, but more hope exists than usual for a team that just unloaded its lone superstar.

Beyond this season, the Blazers will have the ability to accumulate more young talent or package future picks in trades for instant-impact players.

The Blazers still owe Chicago a first-round pick stemming from the 2021 trade that brought Larry Nance Jr. to Portland from Cleveland and sent Lauri Markkanen from the Bulls to the Cavaliers. The pick is lottery-protected, making it somewhat advantageous for the future if the Blazers were to fail to make the playoffs this upcoming season.

As for now, the Blazers will have their own first-round picks in 2024 through 2030 with one eventually going to the Bulls assuming Portland makes the playoffs before the 2026-27 season. If not, the Bulls must take a second-round pick in 2028.

For now, let’s figure at least six first-round picks for the Blazers over the next seven drafts.

The Blazers will also have an additional pick in 2024 (top four protected from Golden State) and two in 2029 (Boston and Milwaukee). That’s at least nine first-round picks over the next seven drafts.

It’s unlikely that the Warriors’ pick will be in the lottery. Same for the Celtics pick in 2029. Boston, led by Jaylen Brown, 26, and Jayson Tatum, 25, figure to be good for a long time.

The Bucks’ picks in 2028, 2029 and 2030 have potential to land in the lottery.

Lillard’s contract runs through the 2026-27 season, but 28-year-old Antetokounmpo should still be quite good in 2027-28 and will likely have the Bucks in playoff contention.

The best bet for the Blazers to land a lottery pick out of all of this will come in 2030 when the Bucks and Antetokounmpo could be on the downswing or maybe he had been traded.

Regardless, nine first-round picks and two swaps in the next seven years give the Blazers assets that could be moved in deals for proven players. And they still could net a pick by trading Brogdon or Williams down the line.

In the end, the Blazers and Lillard departed ways in an unsavory, public dispute. But Cronin did well for the franchise while Lillard landed in what should be a winning situation.