If he was perfect Toews wouldn't be on that terrible contract either.

Yeah thats an obvious one too, but I was looking what they could keep from the past if toews was at say 8.5 or 9 mil and there was nothing else... the team is still under next years cap projection at 10.5 so I figured I would leave it but in an ideal world they sign matching 8x$9 mil contracts and save $3 mil a year.

6M is way too much for thorton

Probably, but on a 1 year deal if you are trying to win a cup... that's market value, he fits perfectly on that line they would dominate.

The Toews contract isn't as terrible as some make it seem.

It's great to imagine a "perfect" GM, and it's easy (plus fair) to point out Bowman's missteps. I don't think you're looking at the right ones, nor are you remembering a lot of decisions were based on the cap. I thought the Bickell contract was bad, but they had the room, and his Multiple Sclerosis was just beginning to onset so it wasn't known until after the trade. They needed to move him, and the price was Tuevo.
I disliked seeing Versteeg go after the 1st Cup, but you do realize he's been oft injured and hasn't scored 20 goals in a season since 2011-2012, right?
I also think you're forgetting that Q didn't want to play Leddy. I know Leddy is talented, got a big contract from NYI and I don't understand why, but Leddy was firmly a bottom pair-preferably 7th defenceman for Q. Look at the average TOI in the playoffs his last two season with the Blackhawks.

The moves I'm more critical of are the trades. He needed to trade Sharp to get under the cap, but Garbutt & Daley in return? And then he flipped Daley for Scuderi's cap hit? Yeesh. Q disliked Leddy and he was about to get more expensive, but Pokka hasn't panned out. Did they really need Vermette? I know he scored a few winners, but was he worth the picks they traded for him? Idk.

But at least Bowman made moves to win Cups. Look at Yzerman in Tampa. Built this great young team, widely lauded for convincing a few stars to sign below market contracts & remain w/the team, stared down a pouty young player...how many Cups? Did they make the playoffs last year? What deadline moves have been made that put them over the top?

When Toews signed that contract he was scoring at almost a point a game pace, so how was Bowman supposed to know the he would slow down. If it were up to me I would rather have Toews at 10.5 than not have Toews at all.

For me it is more of a negotiation thing... it seems like whoever walks into Bowman's office gets whatever they want... I think Toews and Kane could've easily gotten 9 or 9.5 instead, Panik pretty much said there wasn't negotiation that Bowman's first offer was more than he even expected to negotiate for, Bryan Bickell never even averaged 0.5 points a game and nothing stood out about his game, I don't think one playoff run warrants a 4x4 contract. It seems like Bowman tries to compensate too much, while that is admirable and I'm sure players love it, it is detrimental to the long term success of a franchise that could still be in the conference or Stanley Cup finals each and every year. If Bowman only takes back three of his moves this is a completely different team... 1.) Trade Sharp for someone on an ELC to keep Saad 2.) Handle the Bickell situation better to keep Teuvo and 3.) Don't trade Danault for two rentals that your coach is gonna healthy scratch the whole time. Honorable mention: obviously a little more wiggle room on the awful Seabrook contract gives them an extra middle 6 forward on the roster, or helps sign a decent D-man for a struggling core.