Should Celtics Consider This Hypothetical Trade For Damian Lillard?

Portland Trail Blazers All-NBA point guard Damian Lillard appears to be reaching his breaking point with the organization.

Lillard reportedly could be “out the door” after backlash following the Trail Blazers’ reported hire of Chauncey Billups as their next head coach, per Yahoo Sports’ Chris Haynes. Haynes further indicated that Portland’s ability to build a championship roster was in question by Lillard.

Lillard, of note, always has expressed his desire to stay in Portland and deliver a NBA Championship. He has, perhaps unlike other stars, remained committed. However, with reports indicating a souring relationship between Lillard and the front office, it could very well result in the six-time All-Star opting for a change of scenery.

The Boston Celtics have joined a list of teams which could make a push to trade for Lillard. Sports Illustrated’s Chris Mannix had acknowledged the C’s are in a good spot for such trade.

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Bleacher Report’s Andy Bailey on Monday put together a hypothetical trade package from four different teams including the New York Knicks, New Orleans Pelicans, Philadelphia 76ers and Celtics.

Bailey’s trade from a Celtics angle is as follows: Boston sends Jaylen Brown, Marcus Smart, a 2023 first-round pick and a 2025 first-round pick to Portland for Lillard.

“This might be the toughest sell of the list,” Bailey wrote. “Every team in the NBA is after wings who can hit threes, defend and do a little playmaking. The Boston Celtics have two of the best such wings in the league. And theirs are young.

“Breaking those two up just four years into their partnership would require an incredible player in return. Lillard, of course, is that, but he also turns 31 in July. Brown is 24, and he just averaged 24.7 points with a 39.7 three-point percentage.”

Pairing Lillard with All-Star wing Jayson Tatum would make for an absurd offensive tandem and one worthy of contention in the NBA Finals. The Celtics, however, would lose a lot of their defensive versatility and it wouldn’t help their depth chart, which features a number of bigs and limited capable guards. Boston’s championship window if it was to deal Brown and get Lillard in return would speed up exponentially, though.

The potential certainly is intriguing, but we can’t see president of basketball operations Brad Stevens pulling the trigger on it. Everything Stevens has said thus far is about building around the tandem of Tatum and Brown, not eliminating one of them from the equation.