What does “sittin’ in the catbird seat” mean?

Popularized by baseball announcer Red Barber, “sittin’ in the catbird seat” means sitting pretty or being in an enviable position.

The Mississippi-born Barber used this 19th-century Southern expression while announcing games for the Brooklyn Dodgers in the 1940s and 1950s, and in the 1950s and 1960s for the New York Yankees.

A catbird is the common name for the North American thrush (Dumetella carolinensis), whose cry resembles a cat’s meow.