I've wondered this exact thing. How can a bozo like this make billions in the pharma world. It doesn't make sense, he doesn't seem to have any gages of anything.
It's sadly very simple IMO: Katz lacks the ability to judge what an executive in the hockey world has actually accomplished versus what their subordinates have contributed. In the pharma/business world, he has the benefit of market performance along with a litany of public metrics like CAGR, COGS, and inventory turns to evaluate if someone is a good businessperson. I'm sure he is great at drilling down into the details when interviewing a CFO or COO because he knows that world so well.
However, hockey has no such golden KPI outside of the Stanley Cup, and the infrastructure needed to win one is often put together over a much longer period of time than a traditional business. A great scout can unearth a draft class full of great players, but it will often be 5-7 years before that is known. By then, that scout may have moved on or retired, and the GM in charge at the time will reap all the rewards and thus praise. The same goes for a great coaching hire, who can pre-date the management team that hired them.
It is no coincidence all three GMs who snowed Katz in the McDrai era were/are smooth talkers who came armed with a bunch of cool stories and at least one championship each. However, that has nothing to do with their record in terms of trades, scouting, coaching staff hires, and so on. To evaluate those things, you need to look at the complete picture, and discern who was in what role when and how they helped shape the team as it was when it actually began contending.
That is of course not something a pharma turned real estate tycoon would instinctively know how to do, and to be fair I think Katz did try to install "hockey people" who could help make those determinations for him. However, he let Kevin Lowe talk him into hiring a Hockey Canada lifer with zero professional success as his North Star. As it turned out, Nicholson had no idea what criteria to use either, so he relied on the same shallow analysis. This is how we ended up with Chiarelli.
When that failed, Nicholson (and Lowe) just went back to the Hockey Canada well, and hired Holland. Again, no real critical analysis was done, and we overlooked both McCrimmon and Zito x2 in favour of the more "accomplished" person. We've seen how that worked out, and in a fit of desperation, Katz turned to his franchise player's agent- someone whose job it is to literally convince others of their or their clients' greatness regardless of the facts- who himself had less than four years of front office experience.
We are now seemingly back at Square -1 with a GM who reaped the rewards of a prior hockey operations staff and then-fresh cap world to construct a consistent Cup winner, but had little experience building the pieces needed to get there. Our scouting staff remains pitifully small, our analytics personnel are either not trusted to do their jobs or are just not very good, and all key decisions seem to involve low-effort solutions that do not address the cause of the problem.
There is no easy fix for this. At best we can hope Bowman and Jackson prioritize a goalie this summer, figure out what error(s) in logic led them to striking out so badly in FA, and determine whether the coaching staff needs a tweak or another full-on purge. But there is no guarantee any of that happens, and until then, Katz will continue to build a very unflattering legacy that will swallow any success he had before.