By all American Metrics of Success, Dan Snyder won.
In 1999, he purchased the Washington Redskins (and their stadium,) for $800 Million.
This week, he is on the verge of selling the team for $6 BILLION. Despite being the worst owner in the NFL, and his tenure being riddled with multiple scandals, he avoided prison and is about to cash in. So he didn't win the Super Bowl, who cares? For Snyder, not raising the Lombardi Trophy would be like owning a Taco Bell, but not winning Franchisee of the Year before being sold at an incredible profit.
By all American Metrics of Success, Avram and Joel Glazer won.
In 2003, the Glazers bought a minority share in Manchester United and then took majority control of the Premier League team in 2005 for £800 Million. Despite being the worst owners in the Premier league, and their tenure being rocked by multiple fan protests, the Glazers are about to cash in.
Manchester United may not have won at their traditional clip, but the Glazers won hardware in every Domestic Competition since they assumed majority ownership. They also won both the Champions League and the Europa League.
According to CNN, the Glazers are entertaining offers of $5-6 Billion. Today, United share prices dropped on rumors that the Glazers may want to keep the team. Don't believe those rumors, the Greedy Glazers are trying push the sale price to $7-9 Billion. They want to shatter the record for the most expensive sports franchise sale in the world.
What are they going to do with all that money? Re-invest in Washington D.C. or Manchester, England?
You're funny, they plan on lining their coffins with $10,000 bills.
If there was any justice at all, part of the sales contract for both franchises would include a provision that would put the selling owners in stocks for the day and allow the fans to pelt them with rotten fruit.