The Celtics did not land Damian Lillard and, depending on whom you ask in and around the team, they were never really trying all that hard to get the Portland star, for a few reasons: because the team knew he was not much interested in coming to Boston; because his age (33), injury history and future salary (four years, $215 million) are prohibitive; and because the Celtics have had bad history with scoring point guards who play little defense.

Those problems now belong to the Milwaukee Bucks, who are hoping to get some measure of championship-caliber play from Lillard before his inevitable decline.

The Celtics are not much afraid of this Bucks team, even with Lillard added to the mix. Lillard has produced well offensively in his career in the postseason—he has averaged 25.7 points and 6.2 assists there—but he is the type of player who can be forced to become a volume shooter by a smart defense in the playoffs. His field-goal attempts rise from 18.6 during the season to 19.9 in the postseason, while his career field-goal percentage drops from 43.9% to 41.2%.

He also becomes reasonably easy to isolate defensively in the playoffs, which is one of the major reasons that, in 11 seasons, Lillard’s Blazers won four total playoff series and advanced to the conference finals only once, when they were swept by the Warriors in 2019. The Celtics, as a team, have done well against Lillard, holding him to 22.4 points, tied for Lillard’s second-worst output against any NBA team. He has made only 39.3% of his shots against Boston, also ties for second-worst in his career.

Handling Lillard would be a lot more palatable with Marcus Smart still aboard, but Smart is in Memphis now, and the Celtics would have to rely on Derrick White and/or Malcolm Brogdon (maybe) to keep Lillard corralled.

There is another option out there for the Celtics, one already being discussed around the NBA. The Bucks had to send out Jrue Holiday as part of the deal to add Lillard, and Portland is looking to cash in holiday for further young assets and draft picks. The Celtics could make themselves a factor in Holiday discussions, but only if they can get the Clippers to take on Malcolm Brogdon, which was the original crux of the trade that eventually sent Kristaps Porzingis to Boston.

Now, the Celtics again need the Clippers in the pursuit of a top-level upgrade. Only problem is, it would cost Boston the remainder of the team’s fabric to make it happen.

To be able to reroute some of the Clippers’ young talent—players like Terance Mann, Brandon Boston and/or Kobe Brown—to Portland, the Celtics would have to send Brogdon to L.A. They’d also have to send some draft picks to the Blazers. But to make the money work, Boston would also be required to add Al Horford, likely to the Clippers. That would be a tough pill to swallow. If Smart was the team’s heart, Horford is its soul, and following the trade of one by dealing away the other would do serious damage to the Celtics’ culture.

Team president Brad Stevens has shown he is not afraid to make that choice, not afraid to make what he thinks is the right basketball move and worry about the chemistry issues later. It was something he had to deal with plenty as a coach, as when Danny Ainge dealt away Isaiah Thomas for clubhouse headache Kyrie Irving, or let veterans like Al Horford and Gordon Hayward walk in free agency.

The Celtics came into the offseason with Brogdon, Horford and Smart on board, and if they come out of the offseason with Holiday and Porzingis in their place, Stevens will have to look at that as a win. It would be a serious talent upgrade, and if it comes with the added bonus of keeping Holiday from going to Miami or Philadelphia, all the better.

Either way, the Eastern Conference has undergone something of a shakeup here. But whether with Brogdon and Horford, or with Holiday, the addition of Lillard should not scare Boston too much.