Quoting: MitchJr
Sharks have been awful for 5 years; I hope the prospect pool looks good. Not sure we can say Grier has done a good job with rebuild - he’s retaining massive $ for crazy number of years and returns on those trades were underwhelming. Book is still firmly out on Grier imo.
The $ retained is actually pretty minimal, it's just the term and the amount of them making it so they can't retain on any more. 1.5M on Karl, 1.3875M on Hertl, and the expensive one is $2.72M on Burns which ends after next season.
As for the trade returns looking underwhelming:
Karlsson was seen as one of, if not the, worst contracts in the league prior to his 101 point season and was a very injury prone 33 year old and he managed to get out of most of the last 2 seasons by taking on a couple of bad deals that had 1-2 years left on them (Hoffman was horrible but just 1 year, Granlund had been moved for a 2nd at the prior TDL and had underperformed in that short stint, but he's played well here, Rutta was meh but he's not THAT expensive). In addition to that he got a 1st that's looking like it'll be right around 11-13 but could become an unprotected pick next year.
On the Meier deal I was initially underwhelmed but Zetterlund's been great and he's still fairly young, Musty who we got with the 26th pick is looking fantastic, Mukhamadullin looks like he could be at least a top 4, maybe even reach top pair, and we still have a 2nd round pick looking like it'll be around 40-45.
I'll agree I'm not happy with the return on the Burns deal but he had a 3 team trade list and not many teams he'd accept a trade to had space for him. It sounded like from what was said at the time the deal was mostly doing him a favor.
Hertl the part I'm least happy about is the team he went to. It's not Grier's fault Joe Will signed him to that contract when it was clear to pretty much everyone outside of the org that the team should rebuild, from the sounds of it Hertl wanted out and was misled to believe the team would do a short retool, not a full rebuild, and he still got 2 1sts back. Hertl is unlikely to be worth anywhere near his deal at the tail end when the Sharks are looking to compete so it was ideal to get rid of him when he could get a decent return and not wait too long. It'd be nice if the 3rds weren't included and even nicer if they were coming to San Jose, but I'm willing to wait and see. Hopefully Vegas does terribly next season and the Sharks somehow end up with a lottery pick from them (not likely but a guy can dream).
The most valuable thing is what he does with the cap space the deals freed up. I know there's no retention slots next year, but generally retention slots get mid round picks back while taking on bad deals is how teams get the big returns. They have around 39M in available cap space with 11 players under contract for next season and they have some RFAs they'll likely sign who will be making around 1-2M to take more of those slots, so they'll have plenty of space to take on bad deals.
As to the team being awful for 5 years, they'd traded away their 1st rounder in 2020 (ended up being 3rd overall and arguably the best player in the draft in Stutzle) and their 2021 2nd rounder in the Karlsson trade. They did acquire a 2020 1st trading away Goodrow but since Tampa won the cup it ended as pick 31, and Ozzy's not completely done but strong chance he's a bust. They've had 2 top 10 picks, 26, 27, 31, 34, 36, 38, and 45. While 9 top 50 picks in 4 drafts is good it takes time to build up from one of the worst prospect pools in the league which is where they were around that time. Prior to that they'd traded away their 2019 1st for Kane, in 2018 they gambled on a high risk, high reward player in Merkley and he busted, the player they picked with the 2017 1st (Norris) was included in the Karlsson trade, and they traded away their 2016 1st.