He's not giving up 3 1sts, no way

No way is Yzerman giving up 3 1st just not happening.

Callahan is a bit overpaid but you just valued him way, way lower than Bolland. Since he got picked for the World Cup this year, there are some people who would disagree with you on his value.

There are, but I would have to respectfully disagree with them. First, even if you think Callahan is still a top six talent in the league, power to you, but with Hedmans extension kicking in, and Drouin ELC expiring next season, not too mention Kucherov still needs to be signed ... you're going to run into some cap issues and end up having too get rid of top flight young players, instead of your older vets who aren't contributing as much as they have in the past, just look to Chicago and see what happened to them. If Yzerman wants to keep Callahan great, but something's going to give and you're not going to like it when it does. In regards too him being on team USA that's a BS argument in my opinion. The USA selection committee did a terrible job with picking their roster, taking (in comparison to their options) unproductive players like Callahan and Abdelkader, over top talents in the league like Kessel and Johnson. Not to mention USA's talent to select from isn't as deep as Canada's for example, so of course they'll have some weak links.

They way i Look at this Trade is this, Vanriemsdyk is worth a 1st and a second, taking back Callahans contract will get you a 1st and a second, those two second plus the two Toronto give up are worth a 1st and two 3rds.

My point was that Bolland was moved for one top prospect and Callahan is way more valuable than Bolland. Yes, if SY keeps him it will cost a forward, probably Killorn, but the difference between Killorn and Callahan is not 3 1st round picks for any sane person.