They need to move Mo Williams, Antawn Jamison and Daniel Gibson. Those players are over-paid and have no future with the team.
The rest is patience. Be bad for a few years and build up their talent base through the draft. Then when they have their core together, or the beginnings of a core, make further additions via free agency and the draft.
Jamison and Williams are clearly overpaid relative to their current production and have no future in Cleveland, but how to move them without giving up young talent and draft picks that they should be trying to keep?
Gibson makes just over $4 million this year, right around what Nate makes. Not over the top, but he has 3 years left. Can he be a start-worthy 2-guard next to Sessions? Hickson may have some potential in him, too, but that's really all I see. Sideshow Bob is a role player only worth having on a contender. Trade him, even though he's one of their better guys?
Sessions/Gibson/Small Forward/Hickson/Sideshow Bob.
Not great, but if the right SF gets plugged in, they might be okay in fairly short order? Despite being overpaid, Mo Williams, Moon, and Jamison might be a strong bench.
Are they only one player away?
Mo Williams, Jamison and GibsonMo Williams should have solid value. He earns about $8-$9 million. A fine contract for a 17ppg scorer at the point. Someone that needs an upgrade at the point would at least give up an expiring contract for him. Probably a bit more.
Maybe someone like Sacramento in exchange for cap flexibility and possibly a Donte Greene or Omri Casspi. Or a pair of future second round picks or maybe even a late first rounder instead of a young player. Plug Mo Williams in as a starter alongside Tyreke Evans. Something along those lines.
A contender with an expiring contract would probably be willing to take on Antawn Jamison and the extra year on his deal in an effort to put them over the hump. If they can't find that offer ... wait another year, try to trade him as an expiring contract then.
Daniel Gibson has negative trade value. Very difficult to move him. Maybe they get lucky and someone desperate wants a shooter. Or someone is willing to take on his deal instead of giving up a young player or draft pick for Mo Williams. Or the Cavs find a suitable trade for a superior role player with an equally bad or worse contract.
Or they could just be stuck with Gibson ... but it's only a small contract, so as long as they move Mo and Jamison, that will be fine.
Cleveland's GoalThe Cavaliers goal should be to build another contender. Not on okay team, a borderline playoff team, or a playoff team that loses in the first or second round every year. A contender.
The worst place to be in the NBA is stuck in mediocrity because the opportunities to improve your team are limited. You either want to be a top team, on the road to being a top team or rebuilding with the goal of building a top team in the future.
The Cavaliers do not have enough positive assets
(trade assets + draft picks + young prospects + cap flexibility + quality established talent) to improve their squad on the run and realistically expect to field a Championship contender down the road.
They need to be patient and build up their assets and the best way to do that is through the draft. So accept losing and rebuild properly. Add a few top young prospects through high draft picks and build a new team around them.
In summary ... blow it up and build through the draft.