Before 1999, football fans really had no reason to know who Daniel Snyder was. He was just a businessman that owned a communications conglomerate. There are a lot of people like that out there. Of course, 1999 was the year that Snyder decided to invest in the NFL, specifically by buying Washington's football team.
He purchased the team and what was then Jack Kent Cooke Stadium for $800 million after Cooke's death, and has been slowly torturing the team's fanbase ever since. Things got started pretty early, too.
A few months after he bought the team, Snyder was invited to give a talk at the University of Chicago Booth School of Business. The discussion was moderated by renowned economist Richard Thaler, who was recently awarded the Nobel Prize in economics. He relayed the following story about his interaction with Snyder, which is just a perfect encapsulation of the owner:
The paper Thaler is referring to is "The Loser's Curse: Overconfidence vs. Market Efficiency in the National Football League Draft," which he co-authored with Cade Massey. (Hence the term Massey-Thaler Surplus Value, which is used often in football analytics circles.) In the paper, Massey and Thaler argue that most NFL teams are over-confident in their ability to evaluate prospects and thus, the best course of action is to trade down and amass more picks, giving your team more rolls of the dice.
According to the timeline Thaler laid out, he had this conversation with Snyder sometime between when he bought the team in May of 1999 and the first draft for which he owned the team in April of 2000, and Snyder was receptive to his ideas... and then Washington went out and traded third-, fourth-, fifth-, sixth- and seventh-round selections in 1999, and first- and third-round selections in 2000 to the New Orleans Saints for the No. 2 overall pick in the 2000 draft, which they used on LaVar Arrington.
Note: This is incorrect. The Saints traded all those selections to Washington for Ricky Williams, not the other way around. We regret the error.
Now, LaVar Arrington wound up being an awesome player, so it turned out the staff in Washington was right in its evaluation. But he also only lasted six seasons in Washington and seven seasons in the NFL before injuries knocked him out of the league. The team also didn't make the playoffs for another five years after drafting him.
We should also note that Snyder didn't learn his lesson after the Arrington trade resulted in getting a good player but not much in the way of team success. Washington did the same thing in 2012, dealing first-round picks in 2012, 2013, and 2014, and a 2012 second-round pick in 2012 to the Rams for the No. 2 overall pick in the draft, which they used on Robert Griffin III. Griffin had a magical rookie season and led Washington to the playoffs, but he tore his ACL and was never the same.
Washington has been back to the playoffs once in four seasons since that injury, and has made it there just four times in the 17 seasons Snyder has owned the team. So maybe Snyder should've listened to the guy who wrote the book on how to game the draft.