Immediately after acquiring Jrue Holiday from the Milwaukee Bucks as part of the lucrative package for their seven-time All-NBA point guard Damian Lillard, the Blazers have announced that he’ll be on the move again before ever putting on a Portland jersey. Headed into a complete rebuild around two young guards, Anfernee Simons, 24, and Scoot Henderson, 19, there’s no need for the 33-year-old Holiday’s services. They’ll likely seek young talent and draft capital in exchange for the five-time All-Defensive Team guard coming off his second All-Star game nod. Can Chicago put their best offer forward or entice multiple teams to engage in a multi-team deal to land the star point guard?
Before scoffing at the idea of shipping off Zach LaVine for Jrue Holiday, this would not be a direct two-team deal. While Portland has little value in Holiday, they’d have even less value in LaVine’s scoring prowess and on-ball offensive skills. This trade would require including a third team with young assets or draft capital and shipping LaVine there while Holiday comes to Chicago, and the young assets or draft selections head northwest to the Blazers.
This could include any teams who, like the Bulls, missed out on the Lillard sweepstakes and are looking for a consolation prize of LaVine or DeRozan. For example, the Miami Heat was Lillard’s heavy favorite and now returns to the same roster that was only six games above .500 a season ago.
Jrue Holiday would be a legitimate contending move for Chicago, adding an All-NBA level defender, a former NBA Champion, a reigning NBA All-Star, and a career of 16.4 points, 6.5 assists, and 46% from the field player. His play style of primarily distributing and ball-handling, spot-up three-point shooting, and elite defending would fit the mold of the Bulls roster much better than LaVine’s game. This would allow Nikola Vucevic and DeMar DeRozan to be the features of the offense, with a lockdown perimeter defender to limit the opposition’s best guard, the type of defender the Bulls haven’t had in the starting lineup since Jimmy Butler.
If they’re not shipped off in part of the deal, Coby White and Ayo Dosunmu would assume bench roles with this acquisition. One or both would likely be gone with their youth and potential. A team like the Blazers would possibly even welcome either 23-year-old guard as part of their rebuilding process in the hypothetical trade. If it helps Chicago’s case, Holiday’s running mate and backup, Jevon Carter, also recently inked with the Windy City and could likely help persuade Holiday to pursue a deal with Chicago. A backcourt of Carter and Holiday would be significantly more efficient and better defensively than any the Bulls have deployed in recent history. It would shift the scoring duties to DeRozan, 39th all-time in scoring, and Vucevic, a career 17-points-per-contest scorer.
Can the Bulls strike while the iron is hot and still come out of the Lillard sweepstakes with some profit? Would you be willing to part ways with LaVine and his lucrative contract in exchange for the former champion?
