The answer to this question is subjective. It is left up to individual readers to decide if Santiago is a winner or loser, and you then have to defend that stance. If a reader determines winning and losing only by the amount of physical items obtained, then Santiago is a loser and has been a loser for quite some time. He is a fisherman, and he has been very unlucky lately. In this story, he lands the catch of a lifetime. However, he is unable to bring it back with him. He has absolutely nothing to show for all of his heroic efforts. He cannot feed himself with a story, and no one is going to pay him for a catch that exists in story format only. He battled the fish and the sea, and Santiago lost; therefore, he is a loser. On the other hand, the book does end on a slightly positive note. He dreams of the lions, and these dreams show that Santiago's internal drive and spirit to persevere have not been beaten. He still has life in him, and he still plans to do battle. This is the attitude of a winner in many people's opinion.