On first reading Yudhisthira seems to be one of the simplest characters in the Mahabharata. Always truthful, honest, a model statesman and yet a closer reading of the epic brings out the contradictions that plague him.
All the other Pandavas are well etched out and consistent in their actions. They have recognizable vignettes and their actions make sense in hindsight. Yudhisthira is different.
Despite him being the son of Dharma, the god of justice he is an incorrigible alcoholic and an inveterate gambler. He conspired to lose his kingdom not once but twice and in the same manner. Has a grander fool ever been seen? He also placed upon the betting table his brothers and his wife thus effectively enslaving them. No man with even a vestige of decency would do such a thing and yet we are supposed to believe that he is honest, forthright, infinitely wise and knows what the right thing to do at any point of time is. One can also sense at times his envy of his brothers abilities and their martial prowess. He knows that the kingdom that he holds is not his own doing but the result of his brothers' effort. Even Draupadi is wed to him owing to Arjuna's archery, Bhima's strength and Kunti's stupid promise to have everything shared. Perhaps this is why he places the bets in the first place because he never really feels that the kingdom of Indraprastha and Draupadi are his in the first place.