The Boston Red Sox have finished in last place in the AL East twice in the past four seasons, and though they stand to make the playoffs this year, it's still hard to justify throwing stones from a glass house.
That being said, the Baltimore Orioles are having a disastrous season as they watch their once-promising core fall apart while limping to a last-place finish in 2025. They sold some valuable pieces at the deadline, including longtime center fielder Cedric Mullins, as well as Ryan O'Hearn and Ramón Laureano in a package deal to the San Diego Padres.