Growing up as the youngest of three, I was the last to learn how to ride a bike, roller skate (which I gave up altogether since I was so klutzy), play checkers, backgammon, KerPlunk and most other games. Although I loved playing with my older siblings and while sometimes they showed mercy on me, I pretty much got creamed every time. To be on the losing side most of the time wasn't very fun. You can see why I loved playing with Barbies. No one lost. No one ended up in the emergency room. (You remember the klutzy part, right?)
My parents, however, showed me a great deal of compassion. When I was too young to understand the concept of Monopoly, with their help, they let me be the banker. (FYI, I still like being in charge of the money and to this day play a wickedly good game). Whenever we arm-wrestled, played checkers or Go Fish, they let me win most of the time. I still remember that incredible feeling when I won, because it was so rare. It felt good.
The desire to win never goes away, but it does take a certain personality to let go of always having to win. A close friend, with children of his own, confided in me that when he was a boy, his father never let him win at any game. Not. Once. It was a memory that he still carried.
Victories, real or imagined, mean so much to a child, and can help build their confidence to continue playing the game. So, when our kids were very young, we let them win... a lot. Their squeals of delight and the smiles on their faces were better than our winning any day.
Of course, when there is a winner there is also a loser, so we always made sure to model good behavior and accept our fate graciously, which they in turn adopted-because no one likes a sore winner or loser. Even some adults need to work on that. (You know who you are.)
As our kids got older we didn't let them win as often. We slowly began to challenge them and their skills grew, as did their love of the game and good sportsmanship. By the time they were teens, we could play without holding anything back. Our checkers, backgammon, gym-rummy, ping-pong, and tennis games are legendary. Now they cream us fair and square. And it feels good.