Better chance to win a title elsewhere
Simply put, the grass is definitely greener for Damian Lillard elsewhere. Lillard may be hesitant to request a trade due to the chance that he goes to a team that doesn’t perform up to expectations.
However, there is unquestionably a handful of teams that would instantly give him an increased chance to compete for a ring in the future than the Trail Blazers. A roster of Lillard, McCollum, Norman Powell, Robert Covington, and Jusuf Nurkic isn’t nearly enough to make a deep push in the postseason.
A team like the Philadelphia 76ers comes to mind when thinking of teams that would put Lillard in a better spot to contend for a championship.
Getting to play with Joel Embiid and Tobias Harris would give Lillard the best supporting cast he’s played with in his career.
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Despite him calling Portland home for so long, the sharpshooting point guard would be best realizing that there are quite a few teams that would be able to give him a better chance to chase an elusive title.