It was about two hours before Thursday’s game with Dallas when Trail Blazers star Damian Lillard took a seat on the bench next to Neil Olshey, the team’s architect and president of basketball operations.



With his warmup hoodie over his head and a basketball in his lap, Lillard leaned in to look at Olshey’s phone as the executive illustrated his talking points.



The NBA trade deadline was two weeks away, and after the Blazers floundering after a 133-125 loss to the Mavericks, there’s nothing but speed bumps — Indiana, Houston, at the Lakers, Utah, at Denver — standing between them and the Feb. 6 deadline.



Outside of franchise chair Jody Allen, this bench conversation was a meeting of the top two figures in the organization — Olshey the brains, Lillard the heart — and although it is not uncommon for the two to meet informally like this before games, the optics Thursday were interesting. Especially considering two...