Incidentally, it is quite possible that there will be no lies told in this entire situation. Because their parents are most likely wealthy and influential (not an absolute, but in New Canaan it's pretty likely), they won't have to worry much about 'wins' and 'losses' throughout their lives and learning all that 'get what you earn' stuff. This might be exactly what the real world looks like for them. Get third place - here's your trophy, be mediocre at high school - get your legacy entrance to an Ivy, party hard and do poorly there - go to work in your parent's firm or their connection's firm, make terrible gambles at your job and bring down an economy - connections get a bailout and a million dollar retention bonus.
If I have a complaint it isn't that these kids won't learn the lessons about hard work, wins, and losses and therefore will fail in the real world, it's that it will completely prepare them for their real world life in the aristocracy. Win or lose? baby, they won the day they were born.