Jaylen Brown
The Boston Celtics are big fans of Jaylen Brown. They would not trade him just for the sake of shaking things up on their roster, but for a superstar like Damian Lillard, they would have to consider it. For Portland, that would be the starting point in any deal with Boston.
Jaylen Brown has come along nicely in his career with the Celtics. He made his first All-Star game appearance this year as he has developed into a player that impacts the game on both ends of the court.
Offensively he has settled in as the No. 2 option behind Jayson Tatum, so settling in alongside C.J. McCollum wouldn’t be an issue. His offensive production could rise with Portland, as Lillard was such a central figure in their offense.
Defensively, Brown would be a major upgrade. He can defend four positions on the court, as he is athletic enough to stick with smaller players on the perimeter and big enough to handle some frontcourt players on the interior.
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A big reason Jaylen Brown lands higher on this list than Brandon Ingram is because it would mean Lillard was traded to the Eastern Conference, so Portland would only have to see him twice a year and in the NBA Finals if both squads were fortunate enough to make it there.