Both scenarios are dependent on how the lottery works out...
1. The Celtics win the lottery and are rewarded with a top 3 pick...
On draft night, Joel Embiid is taken as the number one pick in the draft and the Celtics are at the mercy of the team picking second and will either be left with Parker or Wiggins. I believe that the best pick would be Jabari Parker because the Celtics can't afford to waste the rest of Rondo's prime waiting for Andrew Wiggins to reach his full potential. With their second first round pick, the celtics select either Rodney Hood or Nik Stauskas to fill the shooting guard position because they don't plan on resigning Bradley.
The Celtics now enter free agency with four of the five starting lineup spots filled. PG-Rondo, SG-(Hood/Stauskas), SF-(Parker/Wiggins), PF-Sullinger. The Celtics decide that Bradley isn't worth the 6-8 million per year that he has been offered and let him walk. They also release Pressey, Bogans and Babb. They give Humphries a pay cut and pay him 5-7 million per year, while also resigning Bayless for 4 million per year.
The Celtics now must address the odd man out, Jeff Green. Danny finally decides to surrender either the clippers pick, or one of Brooklyn's picks along with Jeff Green and sends them to Houston for Omer Asik.
Should everything go perfectly, the depth chart would look like this...
PF- Sullinger, Bass
C- Asik, Humphries, Anthony
(Should the draft not go our way, replace Hood with Stauskas, and Parker with Wiggins)
2. The Celtics Lose the Lottery and receive the fourth overall Pick in the draft...
Danny Ainge looks at the players he could pick fourth overall and is not convinced that any of them will make a big enough impact on the team. He calls up his old buddy Flip and begins wheeling and dealing. They agree on the following trade that is contingent on Love signing a long term extension with the Celtics...
Celtics receive: Kevin Love.
Flip Saunders has finally come to the realization that Kevin Love is not resigning in minnesota and receives his potential front line of the future, 12 million dollars in cap space, and the ability to pick fourth in one of the most loaded drafts in years.
The Celtics now have two of the five starting line up spots filled, PG-Rondo, PF-Love. Because the Celtics don't believe that Bradley is worth the 6-8 million that he is being offered, they let him walk and decide to draft either Hood or Stauskas with their second first round pick. Now they have three of the five starting line up positions filled, PG-Rondo, SG-Hood/Stauskas, PF-Kevin Love. After drafting Jabari Parker or Andrew Wiggins, the Jazz come to the decision that Gordon Hayward is not worth the 9-10 million being offered to him by the Celtics and let him sign in Boston. Now the Celtics have their small forward. Jeff green again is the odd man out. In the same trade mentioned in scenario one, he is shipped to houston for Omer Asik. The Celtics now enter the 2014-2015 season as one of the best three point shooting teams in the league and a serious threat to Miami and Indiana for the two seed with this lineup...
I personally prefer the first scenario because it better in the long term and is a deeper team. However, the second scenario pairs Rondo and Love together which would be a deadly Pick and Roll/Pop. Can't forget to mention the three point power that this team would have in either scenario.