When has he ever done that? Ever?
He does that when he's picking 25th or later and by that point in most drafts there isn't much difference between that and the guy taken 35th.
Since 2002, the Wings traded a first for 2 seconds or a second and a third in 2011 (picking 24th, forgoing Matt Puempel), 2009 (picking 29th, forgoing Carter Ashton), 2006 (forgoing Chris Summers, a Michigan boy, picking 29th), 2002 (picking 30th, forgoing Jim Slater).
Holland has NEVER traded a pick for multiple later picks unless he was at the absolute tail end of the first round and frankly, you might be better off with two bites at the apple at that point instead of the one late 1st.
When has he ever traded a top ten pick to move back into the second round? The answer is never.
When has he truly reached on a guy with a higher pick? Kindl was supposed to be a damn good player when he was taken 19th. Brendan Smith was a Hobey Baker finalist when he was taken in the first round. Sheahan was a solid defensive center and as recently as two years ago had a 36 point year... in Detroit, no less.
Stop talking out of your ass. Holland messes up enough and has enough actual warts on his resume that you don't have to resort to making them up.