Jay Penske: The Hard-Partying Si Newhouse Wannabe of Bel Air

As the L.A. media otherwise disappers, Jay Penske is in empire-building mode. His hitherto low-profile Mail.com Media Corporation acquired Nikki Finke's showbiz blog and he backed Movieline in April. From what we've gleaned, the guy's a true Tinseltown dreamer.

Age: 30

Residence: The tony Los Angeles neighborhood of Bel Air.

Childhood: Born in New York, Penske went to high school in the Detroit suburbs, where he made the All-American Lacrosse team.

Family wealth: Father Roger Penske, a race car driver, owns Penske Corporation, which owns auto dealerships, leases trucks and makes various auto parts.

Jay Penske: The Hard-Partying Si Newhouse Wannabe of Bel Air

Love life: Has dated actresses Lara Flynn Boyle, Gina Gershon, Jordana Brewster (left) and Devon Aoki (with Penske, top of this post)

Personality: Says an associate, "He comes across as hugely elegant, massively sophisticated then as you get to know him, you see this slightly skeevy side, heavy drinker likes to party."

Business: Penske's Mail.com Media Corporation took a $35 million investment from Steve Rattner's Quadrangle Group in September; but we hear he's been having trouble finding properties to buy.

Sites: MMC runs Mail.com, an also-ran email portal whose heyday was in the 1990s; OnCars.com; our former Defamer colleagues' Movieline.com, celebrity news site HollywoodLife (he shut down HollywoodLife the magazine earlier this year) and now Finke's Deadline Hollywood Daily. It also provides private-label sites to large organizations like sports teams and universities.

Jay Penske: The Hard-Partying Si Newhouse Wannabe of Bel Air

Dragon fetish: Penske also runs Dragon Books, a vanity boutique book store he runs a little Bel Air shopping center. Its placeholder website has been under "redesign" for more than two years. Then there's the Luczo Dragon Racing team, which he co-owns with the chairman of hard-drive maker Seagate Technologies.

Flops: Started Firefly Mobile, selling cell phones for kids, in 2002; by 2006 the company needed a restart.

So how much did he pay for Nikki Finke's Deadline Hollywood?: Seven figures, supposedly. PaidContent's Rafat Ali reports that his company had been in talks with Finke at a lower number. We heard from Finke's editor at the LA Weekly, Jill Stewart, that Finke was talking as if she was looking at "so much money" while she pondered the deal. Seven-figures sounds mighty high for DHD, but if Penske was having trouble making deals, maybe he was willing to overpay.

Aspirations: Penske is said desperately seeking entree to the fashion world, part of a broader quest for elegance. The same associate:

He wants to be a modern day Si Newhouse, he wants to have a glamourous publishing company.

We hope, then, he reconsiders the name Mail.com Media Corp. as the name of his flagship.