Miley’s use of her celebrity status to win a "normal" school contest highlights the unfair advantage her secret identity provides.
Miley and Lilly dress as Hannah and Lola to give the money to Sarah so she can win. However, Amber and Ashley ultimately win by getting money from their parents. Miley "spoils" their victory by publicly volunteering them for soup kitchen duty.
As suggested by the title, "free" money or success often comes with an emotional cost—guilt—when it is unearned or achieved through shortcuts. Cultural References
The episode's title directly references the Dire Straits hit
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Miley’s use of her celebrity status to win
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