Adding Damian Lillard to the mix could be a smart move for Boston Celtics’ championship dreams

Boston Celtics

The Boston Celtics weren’t expected to go out like this. After going down 0-3 to the eighth-seeded Miami Heat, the Celtics attempted to make history, becoming the first team to return from a
three-game deficit to win a series.

Instead, the Celtics are a statistic after putting up little fight against the Heat in Game 7, losing 103-87 at home. It was an embarrassing loss for a team with NBA championship hopes, hoping to return to the NBA Finals after losing to the Golden State Warriors in six games last season. One thing is for sure — changes must be made.

This season, Jayson Tatum and Jaylen Brown, earned All-NBA honors, with Tatum named to the first team and Jayson making second team. This also means both players will be eligible for the supermax extension. The financial hardships both star’s supermax will cause, plus the embarrassing way the team was dispatched in Game 7, could lead to the team breaking apart their two co-stars as early as this summer.

It took the Boston Celtics being down 0-3 to finally find the effort to try. It’s even more troubling that the Celtics’ supporting cast brought a sense of urgency instead of their two stars. This makes the looming decision to extend Tatum and Brown complex.

The Celtics will be able to offer Brown a five-year, $295 million supermax contract, which is $100 million more than the contract amount they would have offered had he missed the All-NBA accolade. The extension would be an ascending deal, with Brown getting paid up to $66 million in the 2028-29 season, making it the largest in NBA history. Why would Brown turn down that kind of money? If he plays out the final year of his four-year deal next season, he will enter unrestricted free agency in 2024, but only the Celtics could offer him the full supermax.

There’s a scenario where the Celtics could look to trade him this summer. But between Brown and Tatum, Brown has been the only one ever to show cracks in the facade between him and Boston, as well as appearing non-committal in interviews, making him the more likely player who would be traded should the Celtics decide to entertain such a move.

The Celtics should look to add athleticism and shooting to their center position while bringing in a point guard capable of hitting the three and drawing fouls. As they try to upgrade their roster, they have moveable first-round picks in 2024, 2026, and 2030 and swaps in 2025, 2027, and 2029. That and their depth could net them better complementary players around Tatum or Brown.

How Boston Celtics can land Damian Lillard

marcus smart
Soobum Im-USA TODAY Sports

The first order of business for the Celtics is addressing the point guard position. Marcus Smart was the Defensive Player of the Year last season but is not the consistent shooter to space the floor and create driving lanes. He is the most likely player to be dealt this summer since he is in the first year of an affordable four-year deal worth $77 million.

The Celtics should go big and target Damian Lillard by packaging draft picks plus Smart and Brown for Lillard. This would pair Tatum with a clutch shooter and playoff-tested vet like Lillard. Lillard gives them a first option in crunchtime while allowing Tatum to remain the leading scorer. The balance would be more complementary than the current Brown/Tatum dynamic. Lillard can handle the pressure of playing in Boston, and a move would give him the best chance he’s ever had of finally winning a ring.

Tatum is under contract through the 2024-25 season and has a player option for 2025-26. His All-NBA selection this season made him eligible for a five-year supermax contract extension worth $318 million after the 2023-24 season. The tough part for the Celtics is that if both Tatum and Brown sign their supermax extensions, they will owe $613 million to just two players. In context, only Smart and Robert Williams are under contract through 2025-26, while Malcolm Brogdon, super-sub Derrick White, and Al Horford are under contract through 2024-25. That leaves little flexibility for the team to improve their roster beyond minimum contracts. If the questions surrounding the two’s fit haven’t subsided in the six years they played together, why would the Celtics make such a massive commitment to an unproven duo?

Upgrading the Celtics’ center position

al horford
Rich Storry-USA TODAY Sports

The conference finals proved they need to upgrade the role Al Horford is currently filling. He failed to protect the paint and shot 29.8% from 3 during this postseason run. It’s time to swap out Robert Williams and Horford’s roles, sending the veteran to the bench in limited service, similar to how the Miami Heat utilize Kevin Love.

The blame for the uninspiring playoff exit doesn’t just fall on Tatum and Brown. First-time coach Joe Mazzulla also admitted to not having his team prepared for the moment. Whereas former coach Ime Udoka relied on bigger frontcourts, often playing Robert Williams and Horford together during the last Finals run, Mazzulla opted for smaller lineups, giving up defensive prowess.

The Boston Celtics’ offense shrunk in the playoffs, devolving into three-point chucking and isolation sets for their two stars. It was in these moments Tatum and Brown failed. Sure, Tatum injured his ankle at the start of Game 7, but his fourth-quarter follies were a trend by that point. Tatum didn’t make a field goal in the fourth quarter of Games 1 or 2 and sat through most of the fourth quarter of the Heat’s blowout Game 3 win. In Game 7, Tatum scored 14 points on 5-for-13 shooting.

With Tatum injured in Game 7, Brown failed to pick up the slack. He had as many turnovers as field goals, finishing with 19 points on 8-for-23 shooting. The two simply don’t complement each other. They thrive in the same spots on the floor, prefer being on-ball, and don’t make high-level decisions as the lead playmaker. Neither are high-level defenders, either. Adding 3-point shooters like Lillard would add tremendous spacing to the Celtics while adding complementary players to Tatum’s strengths and weaknesses.

Neither Tatum nor Brown looked like a player deserving of the supermax. But the Celtics are certain to pay at least one of them and possibly both of them. This failed playoff run didn’t create the dreadful questions haunting the Celtics, but it certainly intensified them. Between Tatum, Brown, and Mazzulla, there was enough blame to go around. But the Celtics have options, a luxury many teams who were eliminated this postseason lack.

Building around Tatum makes the most sense, as does retaining Mazzulla for now. This allows the team to move Brown before overpaying him, hopefully for a star that better complements Tatum’s abilities.

Lee Escobedo covers the NBA for Sportsnaut. You can follow him on Twitter at @_leeescobedo

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