Anfernee Simons
Simons seems solidly in place as a member of Portland's young core moving forward. He's still only 24 years old and posted career highs in points, assists, free-throw attempts and free-throw percentage. He showed growth as a scorer and facilitator, the two areas in which he needed to show the most growth this season.
But he played 46 games, the least of his career with the exception of his rookie season, and it wasn't because of tanking. Multiple injuries kept Simons out of the lineup, which is doubly painful considering he needed all the minutes and experience he could get to become accustomed to being the Trail Blazers' lead scorer and playmaker with Lillard gone.
It's fair to wonder how close Ant is to his ceiling. He just completed his sixth NBA season, and at this point, it doesn't seem like he'll develop into anything more than a complimentary combo guard on a contending team, and one who's a defensive liability because of his size.
Simons would fetch the biggest return of any player on this list. He would be a perfect fit for the Orlando Magic, whose only missing piece is a backcourt scorer and shooter. The Toronto Raptors could have some interest as well.
Simons would bring back at least one valuable first-round pick - potentially an unprotected one in next year's loaded draft - and a young player with Scoot/Sharpe-type upside.
It would be a blow to lose Simons, but if Cronin wants to add some real pieces to the Trail Blazers' roster retool moving forward, trading Ant would be the best way to do it.