He is also a bit of a foodie. Though his Pirates have had 18 losing seasons in a row, Terry remains hopeful they'll raise the Jolly Roger more often than the white flag in 2011.
i don't know the actually meaning of "Pirates " and i feel this line "He is also a bit of a foodie" which means his a hobbyist of food,having no transition to the following line. why he used Though? maybe i am wrong.
He likes food. The sports team (Pirates) that he cheers for (or plays on) has lost more games than they have won for 18 seasons in a row. Terry hopes that they will win more games (Jolly Roger is a pirate flag of conquest) then they will lose (white flag means to surrender) in 2011.
yeah,you're right. thank you.