Former four-time heavyweight champion, Evander Holyfield may be one of Alex's toughest challenges yet. Larger than life in the ring, with a heart of gold, this heavyweight has definitely had some missteps and his 250-million-dollar fortune is dwindling fast. Now, it's up to Alex to help the champ rebuild his brand before he's down for the count.

Ever since he foolishly walked away from a lucrative job as co-host of American Idol, Brian Dunkleman has been struggling and is now a full time Uber driver trying to support his young son. Can Alex Rodriguez help revitalize the career of this infamous Hollywood flame out?