Can Celtics Trade for Jrue Holiday After Damian Lillard Deal?

The Bucks traded Jrue Holiday in a three-team deal for Damian Lillard in a blockbuster days before media day kicks off training camp. Lillard’s arrival drastically changes the east landscape that the Celtics appeared as prohibitive favorites in following reports that Malcolm Brogdon and Kristaps Porziņģis begin the preseason healthy along with their teammates. Holiday landing in the east could alter that quickly, as Bobby Marks reported the Lillard trade won’t go through until the teams involved find a new home for the star guard.

Shams Charania noted the Celtics could join a group of teams, including the Heat and Raptors, as suitors for Holiday ahead of his potential free agency next summer. Holiday makes $36.9-million with likely bonuses this season, before he can decline a $39.4-million player option. That’s a tall task for Boston to match, with Brogdon only making $22.5-million as the potential largest salary that could go out in such a deal. Stacking smaller available contracts like Payton Pritchard, Sam Hauser, Jordan Walsh and Luke Kornet doesn’t work either, and the Boston Globe reported that the Celtics have no plans to trade Brogdon again ahead of camp after speaking to the guard for several weeks addressing his anger over his near trade to the Clippers.

Adding Holiday without moving Brogdon effectively doesn’t work, since such a trade would ideally keep Derrick White ($18.4M) on the roster. Holiday brings a defensive dynamic Brogdon didn’t, while also averaging 19.3 points, 5.1 rebounds and 7.4 assists per game as a 38.4% three-point shooter who helped Giannis Antetokounmpo pivot on-and-off the ball. He scored 40 points against the Celtics in a February win and 51 late in the season at Indiana, but he typically scored between 15-25 points in Milwaukee.

His game compares favorably to Marcus Smart’s, with greater shot-making ability and slightly less strength against opposing fives. Holiday turns 33 next season, his 15th in the NBA. An extension could net him more than $50-million per season over four years, totaling around $230-million. That’s a significantly larger contract than the one White ($27.4M) and Brogdon ($31.5) can sign, even together, not to mention Payton Pritchard’s rookie extension potentially settling around the mid-level ($13M).

Holiday’s agent Jason Glushon successfully negotiated the largest contract in NBA history for Jaylen Brown this summer, and since Porziņģis signing an extension that pays him $30-million annually for the next two years, Boston probably isn’t in position to expand its salary base significantly long-term — particularly if it would cost a projected starter in White or one of the team’s bargain contracts in Robert Williams III (3yr, $37.3M). It’s hard to believe the Celtics would trade long-time leader Al Horford for a guard after extending him two-years, $19.5 million last year.

An argument exists that Holiday would solidify the Celtics’ core as prohibitive championship favorites if the team wants to regain its defensive identity. Holiday finished last season with the 12th-best RAPTOR score thanks to his top-32 finish in both the offensive and defensive category. Opponents shot 45.5% against Holiday on over 13 attempts per game, and he deflected, recovered and contested more loose balls than Smart did last year. Holiday produced 1.00 points per possession running pick-and-rolls, better than White, but worse than Smart and Brogdon.

For anyone concerned the Celtics lost something in Smart physically and intangibly, they’d gain something comparable in Holiday, who Smart respected as one of his fiercest rivals. Antetokounmpo’s bully game could pack a bigger punch playing next to Lillard, with Grant Williams and Smart gone, and Horford possibly heading to the bench. Who better to oppose the Bucks than a former teammate in Holiday?

The Celtics can’t stack smaller contracts until Svi Mykhailiuk becomes trade-eligible later this winter, given that trades must match within 110% this year, so something Boston likes would need to go. That includes multiple first-round picks, with multiple a fair assumption given the number of teams that could contend for Holiday.

The Heat will emerge as favorites to land Holiday, given their ability to match his contract with Kyle Lowry’s, them losing Gabe Vincent and falling short in the Lillard sweepstakes. He makes perfect sense playing alongside Jimmy Butler, and fits Miami’s hard-nosed identity. They’d become a far bigger threat to the Celtics in that case — another consideration in pursuing him. Though Miami could turn around and acquire Brogdon from Portland after.

An argument exists to believe in what Boston imagined this summer, regardless of what the field does. A fully healthy Brogdon returns as a formidable offensive force, a greater one than Holiday one year ago. The Bucks and Heat would forfeit their future assets with such trades, while Boston remains flexible into the future alongside its two stars.

Yet watching anything that happens outside the windows of Auerbach Center that could prevent a championship entering a critical becomes difficult to watch. Especially ones that could lead Boston to not reaching the Finals like one year ago.