On April 29, 1999, the WWF made its return to terrestrial television , airing a special program known as SmackDown! on the fledgling UPN network. The Thursday night show became a weekly series on August 26, 1999—competing directly with WCW's Thursday night program Thunder on TBS . In 2000, the WWF, in collaboration with television network NBC , announced the creation of the XFL , a new professional football league that debuted in 2001.  The league had high ratings for the first few weeks, but initial interest waned and its ratings plunged to dismally low levels (one of its games was the lowest-rated prime-time show in the history of American television). NBC walked out on the venture after only one season, but McMahon intended to continue alone. However, after being unable to reach a deal with UPN, McMahon shut down the XFL. 
And that seemed to be the plan, up until Thanksgiving of 1990, when the Gulf War suddenly became a thing and Iraqi turncoat Sgt. Slaughter was thrust into the role of top heel in the company because Vince apparently thought he could just take anyone and put pointy boots on them and draw millions of dollars. Warrior was unceremoniously dumped as champion, dropping the title to Slaughter at "Royal Rumble" and moving onto a feud with Randy Savage instead, and the world never got that Warrior vs. Hogan rematch for the WWF title. Of course, the backlash from the Iraq exploitation was so severe that they had to move "WrestleMania" to the 15,000-seat Sports Arena instead of the LA Coliseum, so perhaps they should have stuck with their first instincts on that one.
In the mid 1970s, before any of the successes, Vince McMahon, Jr. declared bankruptcy. He blames his first financial failure on a combination of bad advice and bad investments, and gradually regained his wealth through the wrestling business. Unfortunately for the McMahons, it hasn’t been completely smooth sailing since then either. Near the end of 1997, WWE was taking a severe beating from WCW, and there was genuine talk of the company going out of business because they were unable to compete. Although that quickly turned around, the story went quite differently when McMahon tried to compete with the NFL, and lost millions on his own XFL. The market investors we mentioned earlier really did a number on McMahon, too, causing him to lose $350 million in a single day in May of 2014.