CRESTON, Iowa—As a 25-year-old, Pete Buttigieg knocked on doors here in Union County as a volunteer for a Democratic presidential candidate with a relatively thin political resume and an uncommon name.

Twelve years after he played that small role in helping Barack Obama win the 2008 Iowa caucuses—a victory that launched the then-junior senator from Illinois on a path to the White House—Mr. Buttigieg is back, drawing parallels between himself and the former two-term president.

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