When Scrooge milked everyone and pinched and hoarded every penny, and even though he delighted in the thrill of taking advantage, was it really winning?  

How about when Bernie Madoff thought he could fool everyone with his Ponzi schemes, was that winning?

What about when Voldemort delighted in getting his way in murder, torture and other heinous crimes against muggles, was that really winning?

Depending upon the character of the person trying to get their way, their idea of winning may simply mean miser, fraudster or terrorist. 

Each believes that them are winning, but are not winners, but scrooges, fraudsters and terrorists to everyone else.

In other words, "stupid is as stupid does"*, or genius is as genius does; we do what is in our nature and intellectual capability.

Though able to achieve their goals and thus believing themselves to be winners, the miser, fraudulent and power tripping character traits caused outcomes not in line with the Lord's teachings and commandments.

Thus, no salvation or any kind of winning accomplishments which serves humanity in life. 

*From the movie, Forrest Gump.