Because it couldnt be any more true. I mean seriously Gary left Pallet Town driving a corvette while being 10 years old, and with 6 unknown hot chicks which cheered for him, as well as getting a hero's departure from all the high-medium classed citizen of Pallet.
All Ash had was his mom and band of beggars, and poor looking people.
At the indigo plateu gary had the advantage over Ash with his blastoise. Seriously, always had the pokemon of type advantage against Ash. Miracle it was a tie at all.
You kno what else sucks? You battling someone with a pokemon (that maybe almost dead) and you got the gym leaders pokemon down to one HP, And when you use a move to win, the gym leaer uses FREAKIN HYPER POTION! Happened to me ll the time!