The Portland Trail Blazers are no longer straddling the line between contending and rebuilding after star point guard Damian Lillard officially requested a trade. With the inevitable trade looming, the Blazers have a lot of decisions to make regarding how to go about their rebuilding phase.
What are the next steps Portland’s front office should take to jumpstart an official rebuild in the aftermath of Lillard’s departure?
Step No. 1: Determine whether to stock up on more draft picks
This first crucial step depends on what exactly the Lillard trade is. If the Blazers receive another promising guard, such as Tyler Herro or Tyrese Maxey, it would make sense to flip the young asset for future draft picks. Maxey, Herro or someone similar isn’t a great fit for Portland’s roster that is already loaded with talented guards.
In that case, the organization should take a chance to reset on its own terms with future picks it can use to better address positional needs and weaknesses. Portland has a great front office for evaluating draft prospects, headlined by assistant general manager Mike Schmitz, who has been a draft analyst for the majority of his career working for companies including ESPN and DraftExpress.com.
However, if the package includes young talent that fits the Blazers’ roster better, such as Miami’s Jaime Jaquez Jr. and Nikola Jovic, they should hold onto them.
In all likelihood, the trade package will include a combination of young players, draft picks and salary fillers. The first step in the rebuilding process after trading Lillard will be siphoning through the received assets to determine which ones the Portland views as long-term pieces and roster fits.
Ideally, the salary fillers will also be players that Portland can flip for more draft picks.

Step No. 2: Find a Jusuf Nurkic replacement
Nurkic very well may also be included in a trade package involving Lillard. If he’s not, this step will include trading away Nurkic to get off his contract as he doesn’t fit the team’s play style or new timeline.
General manager Joe Cronin should be pursuing a potential Nurkic replacement as part of any Lillard deal in the first place. Some possible options include Nic Claxton, Robert Williams III or Onyeka Okongwu as part of a potential three-way deal with the Heat.
However, if a Lillard deal gets done that doesn’t involve Portland receiving a long-term answer for the center position, then that should be one of the first agenda items to address. The Blazers have desperately searched for a versatile, modern-day center that can switch out onto the perimeter and guard multiple positions.
Portland’s new franchise pieces are all guards, so finding a new center to complement the new timeline is paramount.
If they don’t receive a center right away, this is also something the Blazers could address through the draft in upcoming years. They are in no rush to win right away and could end up using one of their likely many draft picks on a center that has the potential to fill that need they’ve been in search of.

Step No. 3: Keep Blazers guard trio together
There’s been much discussion about whether the Blazers should keep all their guards intact, particularly Anfernee Simons. Simons was viewed as the odd man out when it was believed that the franchise was planning to proceed with Lillard and rookie Scoot Henderson.
However, now that Lillard is out of the picture, Portland should do everything it can to keep Simons. He’s on a team-friendly contract after signing a four-year, $100 million deal last year, which should also be a factor.
Last season, Simons averaged 21.1 points, 4.1 assists and 2.6 rebounds on 45/38/89 shooting splits. He’s still only 24 years old and fits in excellently with the up-and-coming draft picks from the past two seasons.
In the 11 games Simons played without Lillard last year, he averaged 27.9 points, 5.7 assists and 2.9 rebounds. He’s an underrated player who could be in the conversation for the Most Improved Player Award heading into next season.
In addition, Simons has a skill set as a combo guard that can fill in for Henderson and Shaedon Sharpe when needed.
The Blazers will likely roll out a starting lineup with all three guards. In the long term, they might be better off with Simons coming off the bench as one of the league’s best sixth men. But until they find a better starting forward, it makes sense to start all three promising guards.

Step No. 4: Get off Jerami Grant’s contract
The Blazers recently re-signed Jerami Grant to a lucrative five-year, $160 million contract. Their hands were tied regarding Grant at the time, because it was still unknown if Lillard wanted to remain in Portland; this was a signing Portland needed to make to show Lillard that the organization was committed to competing.
It was a unique situation because although Grant agreed, the two parties technically only reached an official deal after Lillard announced his trade request. Nonetheless, the Blazers signed the 29-year-old forward to one of the offseason’s largest contracts.
Now, the team can’t trade Grant until after Jan. 15.
Grant had an excellent season for Portland last year that somewhat justified his massive contract. He averaged 20.5 points, 4.5 rebounds and 2.4 assists on 48/40/81 shooting splits. Grant was a great complementary piece alongside Lillard. He was a great floor spacer who could also get his own bucket and defend wings with his 6-foot-8 frame and 7-foot-3 wingspan.
However, the team does not need Grant’s services. He will help them win games, and regardless of what Cronin says about the team remaining competitive, Portland’s best shot at a championship is bottoming out and initiating a full-on rebuild.
The organization wants Grant’s contract, which includes a $36.4 million player option in 2027-28, off the books. Even if Portland doesn’t get many serviceable assets in return due to the contract, it needs to provide itself with more long-term flexibility.

