But on the other end of the spectrum, when it comes to National Football League ownership, are the following five names.
Whether by cheapness, overspending or just plain dumb decisions when running their franchises, these owners have made many of their fans wonder how they became so wealthy in the first place.
Dan Snyder was smart enough in the business world to become the youngest CEO for a listed New York Stock Exchange company, at the tender age of 32.
In the football world, Snyder's decisions have not reaped the same benefits.
Snyder has time and time again been considered the most overspending owner in the National Football League. His ill-conceived signings of big-name free agents have been known to backfire more than once in a while.
His signing of washed-up, non-inspired veterans Bruce Smith and Deion Sanders in the late 90s cost a load of money for little production.
Although he may be one of the most active owners when it comes to decisions on what players to sign, those signings, such as the unsightly contract given to Albert Haynesworth (how did that turn out?), have long earned him the strong criticism he deserves.
Ever since taking over complete control of the Miami Dolphins, he has quickly tanked the once-proud franchise.
Over last year, and again this season, several reports have surfaced about Ross going behind current head coach Tony Sparano's back in his attempt to find a replacement for him.
But as his fantasies of grabbing a Jon Gruden or Bill Cowher have yet to come anywhere close to reality, Ross has created tension inside the organization, with a team that has been atrocious this season thus far.
You could describe Ross' ownership qualities the same way. He has turned a revered franchise into a joke in his short time with full control.
Ross has brought in many-a-celebrity to have an ownership stake with the franchise, including Emilio and Gloria Estefan, Venus and Serena Williams and Jimmy Buffett.
Now that the Dolphins have actually won a game this season, the only bright light that the team could have had, aside from the warm Florida sun, could be gone. And that's the possibility of drafting Andrew Luck.
So unless the Colts arise from the grave for a couple of weeks, Ross and the Dolphins are stuck in misery. He may not even notice, though, while he's sipping something fruity with the celebs. Now only if they could get some stars on the field.
Though many of the ownership duties have been handed over to his sons, William Clay Ford, Sr. has always been one of the most dysfunctional owners in the league.
The one thing that keeps him from possibly topping this list is the recent emergence of the Lions, and the young players (Ndamukong Suh, Calvin Johnson, Matthew Stafford) that they have to build around.
A couple of years ago the only thing you could find worse in Detroit than the Lions was most likely the auto company that Ford owns. The Lions finished an horrendous 0-16 season in 2008 and looked to be as far in the cellar as one could imagine.
Much of that blame could be credited to injuries and other aspects, but after decades of embarrassing teams, shouldn't we know there's something behind all of that? Or better yet, someone?
Don't let this Colonel Sanders look-a-like fool you; the only thing Bill Bidwell has fried over the years is his own football franchise.
The word "cheap" might as well be next to Bill Bidwell's picture in Webster's dictionary, with all the scrimp-and-save tactics he's put the Arizona (or Phoenix or St.Louis, whatever floats your boat) Cardinals through since becoming sole owner of the them in 1972.
In no way, shape or form will Bidwell be remembered for Arizona's Super Bowl run in 2009, but rather will always be known for his losing ways and willingness to do so.
And with all his stubbornness and ignorance over the years, it's easy to see why the Cardinals haven't been a lasting success and why Bidwell is on this list.
If Dan Snyder looks at the NFL's free-agency period as a shopping trip to NYC's Giorgio Armani's, then Mike Brown looks at it like a stop at the local Goodwill.
The deal that sent Carson Palmer to the Raiders practically fell in Brown's lap. Otherwise, he probably would have Palmer stay "retired" for the whole season.
Brown is as stubborn as they come, and his lack of want to spend comes close to, dare I say it, the Clippers' Donald Sterling.
We won't go quite that far, but at least he drafted a potential franchise quarterback. But Brown has without a doubt failed to carry on the pure football blood that his father had being on the sidelines as the Browns coach all those years.
In the end, the basic facts are, Mike Brown has owned the team for 21 seasons. And in the first 20 seasons, he had only two above .500 seasons. And that is why he is still the league's worst owner.