You are very much either over valuing Joe Milton, or under valuing pick 2.
Realistically the minimum would be 2 for 4,28,39 and Milton. And Cleveland would be dumb to even do that, because they would be passing up one of the only two Blue Chips in the draft and hoping he is there are #4..
Nevermind we would be dumb for doing that because we aren't one player away, we need all those picks to try and have at least a couple contributors come out of the draft...and it would create a need for a backup QB.