Jerry spent a lot of his wealth acquiring the Cowboys, that is true. but he did it by taking on an incredible amount of debt.

He serviced that debt by doing everything he could to turn every fan interaction into a turnstile charging admission. Also he was a leader in naming rights and sponsorships.

He violated League dictates about local sponsorships that competed with national ones (League was sponsored by Coke, Cowboys Stadium by Pepsi). One of young lackey Roger Goodall's first jobs was to negotiate with Jerry over this conflict of sponsorships. In a sign of future hand kowtowing, Goodell convinced the League to go along with the local deals.

Everything you can think of Dan Snyder doing to charge his pubic and fans (and the Packers are headed this way too), Jerry was doing first. Danny excels at it giving his marketing background and Robert Kraft probably has executed the best, but Jerry got there first.

And given the cash windfall he was now reaping, he and the 49ers spent a LOT of money in the new cap era (early to mid 90s). They were the teams that everyone thought would break the rest of the League. But eventually the cap accountants caught up to them and extracted a pound of flesh. Jerry went nearly cap broke trying to keep the triplets together with Deion, but he never was not shy on spending cash for players.