New York Yankees
The Yankees have more money than anybody else but this doesn’t stop them from disappointing their fans. They indeed have a record 27 World Series titles, but the last one came in 2009. Since then, they’ve endured a drought that is an embarrassment to the franchise.
They’ve continuously slumped in the postseason and allowed great opportunities to pass by. Meanwhile, the upstart Mets are threatening the Yankees’ traditional dominance in the city. Their fans have a sense of entitlement but they should take nothing for granted (via The Athletic).