8. Hank and Hal Steinbrenner – New York Yankees
Things might be starting to come together for the Yankees finally, but it’s been a long slog of a decade. After George Steinbrenner passed away, his bumbling sons Hank and Hal took over the ownership. They’ve presided over one of the worst decades in the history of the franchise.
They’ve spent most of the time throwing money at problems without any real idea how to fix them. Obviously, this isn’t a recipe for success. They’ve lost the American League Championship four times in the past decade. The Steinbrenners just haven’t had a strong plan.