That kind of thinking is more defendable when you think you're in Cup contention. However, as executed by Doug Wilson, I felt that he was giving up way too many draft picks in that pursuit to the point where he completely decimated his prospect pool, which is something I don't think any hockey franchise should ever ever do. When a team like the Red Wings was still on top back in the Sharks heyday, they still always had young and upcoming talent being added to the mix. And I didn't think much of his cap management.
Personally, I always thought Wilson's never ending chase of the offensive defenseman that would put the Sharks over the top was wrongheaded and that the bigger problem was that they needed more forward talent to augment Marleau and Thornton on both the first and second lines. Despite the fact that the Sharks did finish as the 1 seed in the conference a few times and even made the Cup once, I don't think they were ever really as close as Doug Wilson thought they were and that bore itself out in a lot of playoff series where other teams would just dominate the Sharks.
In the situation the Sharks are in now, they need to keep buying lottery tickets. Hopefully a few of them end up being stars. The ones that don't, hopefully most of them end up being genuine NHL players. That way you build real sustainable depth in your organization and then down the line when the team just needs to fill a hole or two with an impact player, you make a trade or go after a free agent. Right now, the Sharks still need to add a lot of high first round and second round picks. There's no rush for them to be marginally better right now.
It's kind of funny, but Doug was all about taking big swings. The problem was, when you only target big fish, and those are easy targets, like Boyle, Burns, Heatley, Karlsson, Thornton, you don't need anyone of note in your professional scouting department. Everyone knew those guys were good at the time. On top of that, you are constantly throwing all your picks and prospects at teams to get those big fish, so your amateur scouting department doesn't actually have to be good either. You're not relying on them for anything of consequence anyway. Doug was able to ride the core of Marleau, Thornton, Pavs, Boyle, Burns, Karlsson, Couture, Hertl until they all got old, but when the moment came where, if he wanted to extend that window again by swinging big, he chickened out. That would've been Eichel acquired using the Eklund pick and whatever else was left. I fully expected to see a top 6 of Eichel, Couture, Meier, Hertl, Kane, Labanc/whoever with Karlsson and Burns still on the back end in 2021. When he didn't make the trade for Eichel, and sacrifice the future again, there was no one in the building who had any idea what to do next. With the new regime, I'd prefer they keep one eye on the present, and one on the future. Take the big swings at the right times, but keep the plenty of assets within the organization.