My whole philosophy with the Celtics rebuild has been a dichotomy: trade rondo while rebuilding with a high draft pick or trade the pick to bring in a second Allstar to win with Rondo.
However, lets consider the third option: Draft a franchise player in Wiggins AND try to win next year with Rondo.
Consider the scenario where the Celtics land the first overall pick (to their surprise) and select a franchise player in Andrew Wiggins. However, instead of finding a trade parter for Rondo, they find a trade parter for some of their future picks in order to bring in talent around Rondo for 2015 in order to contend in the playoffs.
Lets say Afflalo becomes available out of Orlando and you're able to pull together an offer of Bass, Bogans, 2015 Clippers 1st and the 2015 Philly 1st. This makes sense for Orlando who is undergoing full rebuild. They can gain future assets while opening up playing time for their current young guys (2 rookies in the upcoming draft, Oladipo, Harkless, Lamb, Moore, and Harris) while dumping some salary and bringing in a good locker room guy like Bass who then becomes a very tradable asset at the deadline for future 2nd round picks.
Lets say Memphis misses the playoffs (could still happen) and that disappointment brings sweeping changes through that organization. Instead of holding out hope for one final year of Zbo and Gasol, they decide its in the best interest of the small market franchise to cash in now and execute a quick rebuild around Conley, Lee, Calates and Davis.
Ainge could pull together an insane offer for Marc Gasol. In a realistic trade the Celtics would give up Olynyk or Sullinger as one of the key assets, likely Sully. However, lets pretend that a trade could be made with multiple future first round picks. Ainge sells the following deal: Gerald Wallace, 2014 BKN 1st, 2016 BKN 1st and 2018 BKN 1st for Marc Gasol. Perhaps a protected 2016 Celtics pick is included.
To round out the offseason, the Celtics make a couple of minor additions. They pay AB 4years $20M. They bring back either Bayless or sign Fredette on a 3 year $9M contract. They use part of their MLE to sign a back-up big (Hump, Mohammed, Diaw, Hawes, Steamer, Aldridge, Lopez, Gray, Smith) or bring back Colton Iverson from abroad.
At the end of the day, all of the extra picks from Pierce, Garnett and Doc are gone. But we've turned our big 3 into the following roster:
Rondo / Pressey / Bayless
Afflalo / Bradley / Johnson
Green / Wiggins
Sullinger / Olynyk
Gasol / Hump / Faverani / Iverson
Retooling the team and keeping Wiggins will help develop his professionalism, his sense of urgency and will make him into a winner. Afflalo and Green are each fringe Allstars and therefore appropriately split a star's money (15M total). This becomes the Gasol and Rondo show. Both will need to adapt, but their combined passing and court vision on offense could become a thing of beauty being surrounded by shooters (Afflalo is a top10 3pt catch and shoot guy this year).
I would start the year with Pressey, Bradley, Wiggins and Olynyk coming off the bench and those three guards could absolutely rip games apart using their defense to create offense.
In 2015 you re-sign Rondo and Gasol and bring back the same team. This team is easily a top-4 contender in the East. It has all the tools to beat the Heat.
In 2016, either Afflalo and Green are let go in free agency and Wiggins takes the torch and leads us into the future with Sully and Olynyk...