In our modern world, we think that winning is important and winning is always better than loosing. As a result, many people are willing to do just about anything to be winners. People are committing crimes just to get some publicity. Athletes are taking performance enhancement drug that often have dangerous side effects just to be winners at a sport. And who can blame them when a star athlete in a popular sport can earn a lot more than the president or even the CEO of a major corporation. And of course there are the many stories of those who have won millions in state lotteries only to have it destroy their family, indirectly cause them serious injury or illness, or turn them into such spendthrifts that in two or three years, they are broke and filing for bankruptcy. So winning doesn't always produce good in our lives.
    Then there are the contests that nobody wants to win (or almost nobody, some people don't care what they win, as long as they can claim to be a winner). Things like the worst dressed at the Oscars, the most obese state or city, the dumbest guy on campus, etc. are not awards one really wants to win. 
    I particularly feel bad for the poor dogs who have won the ugliest dog contest the last few years. When that contest first started, it went to dogs who were just naturally ugly, though often ugly in a way that made them endearing. Lately though, the winners have been dogs suffering from severe illnesses or birth defects and the poor things usually don't live long.
    But the biggest reason why winning in these material pursuits is often not that good a thing is because it causes many to avoid the development of their spiritual side. After all, you can't do much spiritual development when you are traveling the country to participate in hot dog eating contests. It's as if they were contestants on Let's Make a Deal and were given a choice to keep a car or go for the curtain with eternal life behind it, and they choose the car. Sad.