Swap expiring deals and add an asset
The next step would be trading Bazemore. Sorry Baze, you have been great defensively this year but you can’t finish at the rim anymore and your salary is too valuable as an expiring. The next option for the Blazers would be to add a combo forward and send out assets to compensate the other team. Though Marcus Morris is only on a one year deal, the Blazers could use the non-bird exception to bring him back next year. This means paying Morris up to 120 percent of his previous contract.
Morris is the perfect upgrade for this team. A better shooter and finisher at the rim than Bazemore, he would add some real toughness for this team. He can defend threes and fours while playing both positions on offense. His shooting has improved significantly over this season and last, while the Blazers could offer him a two or three-year deal at the market rate to keep him around.
Morris is a starting three in this league, and he has playoff experience too. This option is slightly more risky as you rely on an indication from Morris and his agent that he will re-sign. This does happen from time to time but the player is always a flight risk. This is evidenced by Morris reneging on the San Antonio Spurs and then signing with the New York Knicks in the last free agency.
If there are similar options to Morris in the market on short team deals in return for Whiteside and Bazemore, and they could get assurances from an agent that they would re-sign, then this type of move would be worth the risk.