With LeBron James possibly leaving Cleveland next year, this will be GM Danny Ferry's last chance to get him a championship squad before the big 2010 spending spree.
With that said, here are five burning questions facing the Wine and Gold this offseason.
1. Will Ben Wallace's contract be used as a trading weapon?
In the past few days, numerous rumors have been flying around about the Cavs acquiring anyone from Shaq to the Wizards' Antawn Jamison, among others.
What gives the Cavs these options is F Ben Wallace's $14 million expiring contract, basically a huge trading weapon.
Whether Ferry decides to make a trade involving Wallace or not is up to the team on the other end of the deal. The only complication is the potential retirement question that Wallace has contemplated.
He doesn't have the athleticism that made him a defensive star in Detroit and may hang it up, if not after this season, then after next season.
2. How tight is the no-trade grip on Delonte West?
Going back to the Shaq rumors, one of the turn-off points for Ferry is including G Delonte West in the deal.
A former benchwarmer, West broke out this past season alongside PG Mo Williams. West is a terrific shooter with slashing ability, and he is an excellent defender.
His youth is what makes him so valuable, along with his presence in the locker room.
This might sway Ferry to make the price for getting West much higher than some GMs want to pay.
3. What is the future of Mike Brown?
A report out of New York, which was proven false, stated that Cleveland's front office was torn towards firing NBA coach of the year Mike Brown in favor of Pat Riley and Jeff Van Gundy.
Granted, Brown is not the best coach in the league, but he is easily a top 10 coach, if not top five.
He has drawn great criticism, charging that he lacks halftime adjustments and leaves his offense to his assistants.
But his last playoff series, where he got outcoached by Stan Van Gundy, who was labeled by Shaq as the master of panic, has many fans frustrated, as so many expected a championship.
Brown may be a scapegoat, but he still needs to find a way to consistently get the best out of all his players outside LeBron, or he may be coaching elsewhere.
4. Is Anderson Varejao worth letting go?
Forward Anderson Varejao is a free agent, but he has a very high asking price of around $9-10 million, which the Cavaliers might not be able to afford.
They need frontcourt help desperately, but Varejao provides little outside of hustle, drawing charges, and the occasional putback off the miss.
For what he brings to the table, he is asking for a large amount of money, which has the front office frustrated.
The best option for Cleveland would be to re-sign him and then deal him, although Varejao is unrestricted, which makes the deal very hard to pull off.
In this negotiation, be prepared for a lot of hardball from both sides, but many fans feel that at this stage of his career, and with where the team is at, Varejao is expendable.
5. Can Danny Ferry make yet another great trade?
If nothing else, Ferry is a master at swinging good deals while giving up very little.
Starting with giving up a slew of worthless players for Wallace and West, and getting Williams from Milwaukee for practically nothing, Ferry knows how to make steals.
But the roster situation he is faced with may be forcing his hand somewhat. Everyone knows that the Cavs are looking to improve the frontcourt.
This will make it harder for the Cavs to swing another lopsided trade before the season.
Don't underestimate him, though, as he was able to land Williams under everyone's nose while people were caught on Baron Davis and Vince Carter.
If any GM can give LeBron some pieces to play with, it will be Ferry, although his tactics could be aimed more at freeing salary space to be a player in the great 2010 free agency chase.
No doubt he has his work cut out for him. With the draft in a week, look for Ferry to make a deal to add talent but also find a way to get younger in all positions.