Do some research in the threads around here. As a Chairman, many of us routinely miss upgrades, especially on hub-hub flights and on flights with a large amount of paid F traffic (PHL-LAX, PHL-SFO, etc). Think the other airlines are better??? Try flying UA or DL during peak times on flights between their hubs. Take a look at how long the upgrade waitlist is. Even the top tiers can be number 20 or higher on the list.

Your complaint holds no water and you won't be getting your money back. US did nothing to deceive you as they make it quite clear that upgrades are capacity controlled and never guaranteed, and that Chairman's status only comes with free lounge access after you've flown 125,000 miles in a calendar year. The benefits US affords its preferred fliers are generally in line with all the other legacies.