But he hasn't experienced a playoff win. Now that Ross has decided to assign general manager Chris Grier and Dolphins legend Dan Marino with a new attempt to shake the Miami Dolphins Etch-a-Sketch and start from scratch, he should come to this realization: if this reset produces the same results, he's not cut out to be an NFL owner. It's time to sell the team.
Because just being rich and spending money isn't enough. The Miami Dolphins may be a great investment for Ross, but they'll be here long after he and all of us are gone. It should not just be about money. It should be about the fans.
If he can't get the job done this time, Ross should fire himself.
From terrible choices in regards to management (see: Jeff Ireland and Mike Tannenbaum) to declaring every new coach he eventually fires the next greatest hall of fame coach, Ross has a proven track record of not being to identify what the heck a good front office looks or feels like.
The Dolphins have been bad and embarrassing under Ross, both on the field and off.
On Ross's watch, the Dolphins have been a part of multiple scandals that reached TMZ and Good Morning America levels of media coverage. That's never a good sign for a football team. From the Richie Incognito-Jonathan Martin fueled Bullygate scandal that blew a hole through the Dolphins organization in 2013 to offensive line coach Chris Foerster blowing lines of cocaine on video taken in the Dolphins facilities, the team has been an embarrassment since Ross bought it from Wayne Huizenga.
Really, all Ross has done well since buying the Dolphins is to pour half a billion dollars into a renovation of Hard Rock Stadium. So the real estate guy has proven he's good at real estate.
That's not enoug. Ross has one more chance to get this right. He and the Dolphins new brass should take their time and make sure this one counts.
Because Dolphins fans don't want to be in the same spot in three years.