Picks Would Always Be Hardest Part of Celtics Giannis Antetokounmpo Deal

The Celtics would reportedly prefer to trade Jaylen Brown straight-up for Giannis Antetokounmpo if they do a deal. Judging by the fact that the deal isn’t done, despite the singular power of Brown’s presence in a trade, the Bucks, and other potential third teams in a deal, don’t feel the same way about the structure of a trade.

Each additional revelation, despite the head-twisting nature of the reporting around the Antetokounmpo sweepstakes, makes it more understandable why the talks sit at a standstill only four days from the NBA Draft. The Bucks clearly don’t see the Miami Heat’s package as strong enough, and that allows the Celtics to not offer everything they can in a potential deal, hence reporting around the prospect of Boston trying to pull off a deal without Brown. That’s not realistic, Sam Amick noted, as expected, but the amount of draft capital the Celtics should give up in a trade stands as a legitimate argument. One that even gives me pause as someone in favor of an Antetokounmpo trade for Boston.

Previously, I would’ve went as far as to say that the Celtics should give up most if not all of their future firsts in a trade for Antetokounmpo. The risks associated with the trade, Brown’s presence, the limited competition and the changing cap and draft rules have changed that for me. Now more than ever, you need to draft-and-develop to maintain a sustainable franchise as luxury tax hits and apron penalties skyrocket, a particular reality for a Boston team built around two super-max players whether they move forward with Brown or Antetokounmpo. They’ll need picks to make either core work long-term, and they’ve already traded rights to their 2028 and 2029 firsts.

That allows them to currently trade either their 27th overall pick in next week’s draft, or their unprotected first next year, but not both until July. They can also add a 2030 swap, 2031 first, 2032 swap and 3033 first in line with the Stepien Rule. The Bucks need picks, particularly if Brown, their lone player return in a deal directly with Boston, gets re-routed elsewhere. Milwaukee owes the 10th pick in this year’s draft, still owes a 2027 swap to the Pelicans, 2028 and 2030 swaps to the Blazers, and an unprotected 2029 pick that Portland owns in tandem with their own and Boston’s. The Blazers, for that reason, would’ve become a powerful facilitator in helping the Celtics acquire Antetokounmpo.

Those third teams became additional challenges for the Celtics through this saga, not to cast it as a past pursuit at this point, but one that national commentators continue to view as something of a long-shot considering all the factors involved. Boston’s concern about Brown’s name floating in trade talks became clear in recent days through reporting about their pursuit, which stressed that they haven’t included him in any talks. Talks haven’t progressed, period, others said, while Boston’s frustration with the Bucks’ handling of the process appeared in other reports.

That all amounts to the odds stacking against the Celtics currently if they don’t want to pursue Antetokounmpo with an aggressive package of draft picks, further enticing facilitators in the trade. Those teams like the Blazers probably feel like they could simply trade for Antetokounmpo themselves, but one factor working in Boston’s favor remains the reports that Antetokounmpo would only currently commit to extensions with the Celtics and Heat. That could change, either from his standpoint or a team’s increasing appetite for risk, which would allow a mystery suitor to strike. Orlando, Minnesota, Cleveland and the Blazers are those teams to watch, in my opinion.

Then, there’s the agonizing thought that the Bucks could flex their own leverage in all this by retaining Antetokounmpo beyond their self-imposed deadline of Tuesday’s draft for addressing Antetokounmpo’s future. By then, the Celtics probably have to, for multiple reasons, figure out whether they want the superstar, and to do what it takes to acquire him, or move on and float to reporters that they’re no longer focused on an Antetokounmpo pursuit.

The greatest hope for the Celtics, and one that’s perhaps telling about their path forward beyond this saga, will be that a team decides Brown can lead their franchise forward and go all-in either as a facilitator in the Antetokounmpo trade, or directly trading a massive haul for Brown. It’s unclear whether that trade partner exists at the moment, and what role Brown’s value around the league has played in the Celtics’ ability to get the Bucks their desired trade return for Giannis. As mentioned, the Heat haven’t done enough to push Boston.

So we’ll continue to wait into the weekend.