With Avery Bradley's free agent status looming probably looking for a long term deal this is an interesting question, and when I posed it to myself I found it very difficult to come up with a ranking. Mostly because I don't think there is that much separation from some of these players.
I have left some guys off the list like Kobe who could be out of the league in a couple years, Wade because he always seems to be facing injuries now, and others like Reddick, Kevin Martin, Monta Ellis, and even Afflalo as even though they are better players than Bradley now it seems, they are all around 30 and I worry about a drop off in play within those 5 years. I've also left off very young guys like McLemore who haven't shown much yet in this league.
So here is my list. I've added age and their basic stats.
1. Harden -Age 24, 24.3 PPG, 4.7 RPG, 5.4 APG. Defense might have dropped off but still head and shoulders above the rest.
2. K Thompson -Age 24, 18 PPG, 3.1 RPG, 2.5 APG. Just love this guy's shooting. Nice fit next to Rondo.
3. Beal - Age 20, 16.8 PPG, 3.7 RPG, 3.5 APG. Thought about putting him above Thompson
4. Stephenson -Age 23, 14.2 PPG, 7.3 RPG, 5.2 APG. His around around numbers jump out and maybe you take him over Beal and Thompson if you want that type of player.
5. Hayward -Age 23, 16 PPG, 5.5 RPG, 4.9 APG. Another all around player. Maybe flip a coin between Stephenson and Hayward.
6. DeRozan- Age 24, 22.3 PPG, 4.6 RPG, 3.8 APG. Putting up very good numbers, but maybe not very efficient.
7. Eric Gordon- Age 25, 15.8 PPG, 2.7 RPG, 3.2 APG. Risky pick because of injuries, but if he ever regains his old form a really good player.
8. Oladipo- Age 21, 13.8 PPG, 4.4 RPG, 4.1 APG. Maybe a better version of Bradley. Could move him up based on potential.
9. Bradley- Age 23, 14.3 PPG, 3.9 RPG, 1.4 APG. Love his D and becoming a decent shooter, hate his passing and dribbling ability. Not sure how much more he will improve.
10. Waiters- Age 22, 14.3 PPG, 2.9 RPG, 2.7 APG. Maybe he should be higher. Can't make up my mind on this guy. Seems to pout too much.
11. W Matthews- Age 27, 16.9 PPG, 4 RPG, 2.4 APG. Always forget about him. A little older but should be solid for another 5 years I would think.
12. G Henderson- Age 26, 14.7 PPG, 4.1 RPG, 2.7 APG. Sort of like Matthews. Solid player.
13. Mayo- Age 26, 12.1 PPG, 2.6 RPG, 2.3 APG. Blah. Kind of like the J Green of shooting guards. Has big scoring nights every now and then, but mostly just an average player.
I'm stopping there. How is your list, and would you add anyone else?