If that's the case why wasn't it making money when Jerry bought it?
The economy was in shambles from the savings and loan scandals and the tax reform act of 1986 (TRA86)
Real estate and vanity investments (like the Cowboys) took a direct hit to their value because their values had been pumped up artificially by their tax benefits. In a nut shell, prior to the TRA86, passive losses generated from real estate could be offset against active income reducing the taxes due for people like doctors etc.
So what happened was people were buying real estate that were showing losses after depreciation and then using those losses to offset their primary income tax obligation.
Keep in mind that the highest tax rate was 50% in 1985, so some savvy folks discovered they could create real estate partnerships that bought real estate that generated losses with the primary benefit to investors being that they could reduce the taxes due on their primary business activities and obtain ownership in a hard asset in the process.
1989 was probably the bottom of the market after the devastating effects of the TRA86 and the Savings and loan scandals.
Jerri steps in and buys the most valuable franchise/best brand on the planet at a hugely discounted price without any of the previous investment rationale burdening his investment. He had no where to go but up from that point. He deserves credit for having the balls and wherewithal to buy the team but from that point forward all it took was business 101 to get the ship back on course.
You always make money on the buy and that's what jerri did so well.
Here's an article that describes what was happening at that time:
MODERN HISTORY THE GREAT DALLAS BUST WHAT THE HELL HAPPENED?
Pro-tip: Never buy real estate or any investment when its primary value is derived from a tax benefit that could change overnight and bankrupt you in the process