Besides Madonna, Oseary keeps a small stable of entertainment clients, including Kravtiz, David Blaine and the show "Last Call With Carson Daly." In addition, he's a partner in Untitled Entertainment, whose clients include Ashton Kutcher, Hilary Swank, Penelope Cruz and Naomi Watts. Oseary also has a handful of film and TV credits to his name, including producer titles for "Agent Cody Banks" and "Material Girls" and on-screen roles in "You Don't Mess With the Zohan" and the "Charlie's Angels" movies.
When he added A-Rod to his roster, Oseary fueled speculation that the Yankees hitter may transition out of baseball and into the entertainment biz.
"He's focusing on baseball and needs someone whose interests are aligned," Oseary told Daily Variety in December. "This is to help him have more control of his image and brand. ... Obviously, there are a tremendous amount of opportunities for Alex."
Including, perhaps, a closer bond with The Material Girl. If Rodriguez wants to get in with the entertainment world's elite, he picked the right man. Oseary's relationship with Madonna is more than just business — he's the godfather of Madonna and Guy Ritchie's son, Rocco. When she adopted Kabbalah, so did he. He tagged along with her to that Yankees game she attended in June. He's been romantically linked to Gwyneth Paltrow, Renee Zellweger and Eva Herzigova, no doubt in part because of his connection to the pop music queen.
But right now, Oseary's probably more concerned about staying on good terms with Madonna than doing any of his own wining and dining, or for that matter, doing any other business deals. It doesn't look good that her name's been splattered throughout the press and linked with those of his other clients, and Oseary needs to keep the Rock and Roll Hall-of-Famer happy to stay on top.
"He's very good at putting up a wall around her, at keeping people away, and that's what he's going to do now," Drew said. "As long as he's in Madonna's good graces, he doesn't really have to worry about much else. He knows where his bread is buttered."
Hear that, Lenny and A-Rod? Know where your manager's loyalties (probably) lie.