Do the Penske-Rattner Dots Connect?

Just asking: Is it odd that deposed car czar Steve Rattner poured $35 million into Jay Penske's dubious internet adventure Mail.com in October, and then arranged for Jay's father Roger Penske to buy Saturn from General Motors nine months later?

To be clear, we don't know if the two deals are connected, and certainly don't have any info to suggest there was anything untoward about them. But given Rattner's history of greasing deals—recall that he bought Chooch, a low-budget film by the brother of the chief investment officer of New York state's pension fund, shortly after the fund invested $100 million in Rattner's Quadrangle Group—we thought we'd throw it out there.

Here's what we know:

In September 2008, Quadrangle Capital Partners—part of Quadrangle Group—invested $35 million in Mail.com, Jay Penske's would-be online empire. The money was for "selective acquisitions and new management hires," which means hiring Nikki Finke and Bonnie Fuller. Two of Quadrangle's partners got seats on Mail.com's board. Mail.com had little to recommend it at the time as a hot pick for internet supremacy, and the investment came shortly before Quadrangle would wind down its media-focused hedge fund amid 25% losses, but who knows? Maybe it'll turn out to be a rocket.

Four months later, in January, Rattner's name started getting bandied about as Obama's pick for "car czar," and six weeks after that Rattner left Quadrangle to join the Treasury Department with the goal of saving the auto industry.

One way to do that is to keep Saturn, with its 13,000 employees, alive. General Motors made clear that it couldn't keep Saturn going, so it went on the block. And in June, none other than Roger Penske, the billionaire car mogul who happens to be Jay's father—and perhaps the provider of seed capital to Mail.com?—emerged as a buyer. The terms of the deal haven't been disclosed, but the Wall Street Journal says Saturn's service and parts operation alone has been valued at $100 million.

And then last month, Rattner stepped down amid chatter that Quadrangle, and perhaps Rattner himself, was getting drawn further into the pay-to-play pension scandal that gave us Chooch.

Here's what we don't know:

Was Penske doing Rattner a favor in swooping in as Saturn's savior, or did Rattner hand it to Penske on a platter? Without knowing the terms of the deal, it's impossible to know. But the news of the deal sure made Rattner look like a hyper-competent technocrat calmly steering an industry in crisis. If Saturn had simply been liquidated, it would have been seen as a disastrous signal. On the other hand, according to the New York Times, the brand had attracted "16 potential bidders," so maybe Penske was the one looking for an edge, and maybe Rattner helped him find it. Or maybe Penske was the most rational buyer for Saturn, and it's a coincidence that the guy who was essentially running GM when it was sold happened to own a piece of Penske's son's business.

Given the timeline, it's virtually impossible that the Mail.com deal itself was some kind of sweetener—coming as it did in September, Rattner would have to have had the foresight to know that Congress would bail out the auto industry, and that Obama would win, and that Obama would hire a car czar, and that Rattner himself could land the gig, and that Saturn would need to be off-loaded from G.M. Only under those circumstances would a relationship with Penske's son be something worth having in your back pocket, and Rattner would be a much richer man if he had that sort of vision. (Cf. Maxim.)

So is there any more connective tissue out there that might make render the above datapoints more sensible? Let us know.