Packaging two or three firsts to "move up" to one better pick seems to be the approach that most people are advocating. I would actually be disappointed if that is how it works out. Drafting is so inexact that to give up on one or two hard earned (traded) firsts, just to move up from say 7 to 4 or 11 to 7 or whatever seems like a waste. You just don't know how good either player is going to be.
I think you can trade current picks for future picks. Teams are going to put more value on a mid range pick now than a mid range pick in a couple of years. I think we can trade a mid range pick in the current year (say 2016) for a pick in 2019 plus maybe a second or something like that. The other team is going to think they are getting better and that the future pick will not be that good, which may be the case but we still keep the picks to use in trades or to have multiple picks in future years.
I like having two firsts in a given year. That way you double your chance of getting lucking and picking someone who will exceed the value of the draft slot. With two, chances are (on average) one pick will be a bust and one will be a surprise. Alone the way, maybe one in 5 becomes a really big surprise and that one pick may make all the trades worth it. Drafting is not the game to put all your eggs in one basket in my opinion.
Using multiple picks for players is a safer bet in my opinion. Actual players have a much better track record that you can assess. There is still risk, but less than drafting so that is another part of why I don't want to see Ainge just roll up 2 or 3 picks for 1 pick.
vg, good point and i agree. just to add to that, the philly 2nd rounders actually have real value, more than the tail end of the 1st round does in some cases. the reason is that the 2nd rounders are not guaranteed contracts, so they are easier to jettison if they dont work out. the first pick in the 2nd round may have more value to some GMs than the last pick in the first round.
ainge has lined up value on many levels.
next, your post made me think (which is good). having extra picks in a year gives a GM a chance to wheel and deal, make trades, facilitate other trades for others, lots of options. ainge is a guy who loves to wheel and deal and does well in these situations.
the typical draw back is that such scenarios (multiple picks) do not come along very often.
but look at the celtics. they are staring at multiple picks for years to come, and if they roll some over through trades as you suggest, then that window of opportunities will continue for more years.
i expect the next 4-6 years to be like this for the celtics. ainge will be working hard and have assets to make deals. expect a LOT of changes and tinkering even when they get good players.