Take the word "bondage". Add a vowel somewhere and separate the eight letters into two common words without changing the order. Replace each word with a synonym and you will name something that Ronald Reagan experienced twice while governor and twice while president.
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A:
The title and image both refer to "leap". "Look before you leap" and the US Navy Leap Frogs. Add a U to bondage to get BOUND and AGE. Every four years (almost) we all experience the phrase made up of the synonyms to bound and age.
Leap Day