No, he does not have a two-way contract. He had an Exhibit-10 contract with the Trail Blazers last year. Their current two-way players are Caleb Love and Sidy Cissoko, and they have 13 players under contract, per Spotrac.
I’m not sure what their plans are for Justin Minaya or Bryce McGowens. As of now, there are two roster spots open, as well as a two-way. Bouknight was okay in the G League last year. He still can’t really shoot from outside (30.4% from 3). I’m rooting for him, but he has an uphill battle.