Richard Parsons is the new face of the struggling, bailout-needy Citigroup. The former CEO of Time Warner Inc. (TIME’s parent company) became Citi’s Chairman just days after the company announced an $8.3 billion fourth-quarter loss — its fifth quarterly loss in a row — and revealed that it would separate its retail banking business from the risky assets dragging it down. Citi may be taking on water faster than it can dump it out, but Parsons is no stranger to financial struggle. When he took over AOL Time Warner in 2003, the media conglomerate was $27 billion in debt and the Securities & Exchange Commission had taken a keen interest in America Online’s premerger accounting practices — basically, the company was the Wall Street equivalent of the dorky kid whom nobody sat next to at lunch. Parsons had some success at Time Warner — he removed ‘AOL’ from the company’s name and streamlined its business practices — but by the time he stepped down in 2008 the media behemoth was still saddled with underperforming departments and a stagnant share price. The question now is, what can he do for Citi?