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Steve (or someone close to him) spotted a loophole in the California vehicle laws. Anyone with a brand new car had a maximum of six months to affix the issued number plate to the vehicle.
So Jobs made an arrangement with the leasing company; he would always change cars during the sixth month of the lease, exchanging one silver Mercedes SL55 AMG for another identical one. At no time would he ever be in a car as old as six months; and thus there was no legal requirement to have the number plates fitted.
One might also assume that the leasing company was happy — they had an endless supply of luxury cars to on-sell with the previous driver being none-other that Steve Jobs. That would be a win-win-win situation for Steve, the leasing company and for the subsequent buyer.