For the purpose of this discussion, I'm going to assume that the AD trade doesn't work out if Kyrie leaves. In this case I wouldn't be against a trade for Jrue Holiday under a few conditions.
- Horford would need to sign a new deal at somewhere between $18-20 Million Per Year. This would free up enough cap space to make the deal without sending much in outgoing salary.
- Celtics would need to be able to acquire Holiday using mostly draft picks and young prospects. No core players would be moved in the deal. Incentive for New Orleans would be to get the contract off their books and commit 100% to a rebuild.
I've already mentioned potential cap concerns involved with Holidays contract. It really limits the Celtics cap flexibility for the 2020 and 2021 off-season. Either way, the salaries of Hayward, Horford, Smart, Jaylen (RFA max contract), and Tatum would prevent the Celtics from affording a max free agent next summer.
Realistically I don't think Ainge would be willing to take on Holidays contract. That said, I really like the idea of Holiday as a starting PG for next years team.