IMHO:

1. Seabrook - I said it at the time, the cap hit was too high and the term way too long. One or the other or both needed to be lower. $6.8m for three years? Fine. $5m for 7 years? Maybe Stan is planning to buy him out when the new CBA kicks in.

2. Anisimov - Stan inked him to an extension a year before he needed to, at a cap hit higher than he deserved, and a term longer than he deserved.

3. Toews & Kane - at the time it seemed like that was where the market was heading and they deserved to be the top two paid players in the league. But it was a risk that the Cap wouldn't rise as he was assuming. Stan was wrong. He owns that.

The ones that weren't, IMHO:
- Kruger - I think he over pay was in return for him playing for $1.5m the year before, he got a premium in return.
- Bickel - he'd probably have gotten more on the open market
- Crawford - His pay is in line with other goaltenders at his level
- Keith - some of the previous years he was a bargain at that cap hit
- matt_ahrens

What is the significance of the timing of Anisimov’s deal? If Stan waited a year to sign Anisimov how much would he have garnered after how well he played with Panarin and Kane? Plus Anisimov would have been a UFA at the end of his first season. $4.55 million is about on par with what players like him would get (ie Brandon Sutter and Alex Killorn).

What is the significance of the timing of Anisimov’s deal? If Stan waited a year to sign Anisimov how much would he have garnered after how well he played with Panarin and Kane? Plus Anisimov would have been a UFA at the end of his first season. $4.55 million is about on par with what players like him would get (ie Brandon Sutter and Alex Killorn).
- DarthKane

The cap squeeze. The 15-16 season it had risen $2.4m from the year before. The previous increase had been $4.7m. Then before the 16-17 season, when his new contract kicked in, it only increased $1.6m. I think they were counting on it increasing more, the same mistake he made with 19 & 88's contract. And then there is his FO%... I think Stan thought he'd improve with the Blackhawks coaching but he didn't. (BTW: this year he's at 54.1%, over 50% for the first time in his career. Probably due to the demotion to 3rd and 4th lines and the tighter FO rule enforcement.)

Edit: good comparable though. You're probably right, he got market value. The problem Stan never seemed to understand is that with $21m of cap being consumed by two contracts, and over market, he needed to get a few other guys under market. He's relied on rookies and free agents from Europe for that but needed to get some hometown discounts or something.