A remarkably untimely cloud hangs over Governor David Paterson's apparent selection of Congresswoman Kirsten Gillibrand to replace Hillary Clinton as junior senator of New York.

Federal prosecutors, according to numerous news accounts, are poised to indict former Senate Majority Leader Joe Bruno and no one knows if that possible indictment will contain allegations about a real estate deal that involved Bruno and Gillibrand's father, Albany lobbyist and power broker Doug Rutnik.

What we do know is that prosecutors subpoenaed all the records of this complex transaction which, at the very least, raise stark ethical questions about Rutnik's awkward business relationship with a powerful public official he lobbied. No one familiar with Gillibrand's rapid political ascent would question the pivotal role that Rutnik has played in it, milking his wide-ranging political connections for his daughter.

The governor's office has made it clear that Caroline Kennedy was submarined by questions she couldn't answer in the vetting process, ostensibly involving taxes and a nanny. But it's unclear if Paterson has even considered the possibility that as he and Gillibrand prepare for their 2010 campaigns, her family could be dogged by conflict of interest allegations. The Bruno probe has been so far-flung and well chronicled -- particularly by the Albany Times Union -- that it is impossible to tell what elements of any case against him might consist of, but the deal with Rutnik is certainly an inviting target.

No one disputes the fact that Rutnik was a 25 percent partner with Bruno, Bruno's brother, and another lobbyist in First Grafton Corporation, a development firm that was planning to build luxury homes in Grafton, where the senator lived. The wife of a wealthy businessman, Jared Abbruzzese, whose myriad connections to Bruno have the continuing focus of the probe, wind up buying a 12 acre plot from the Bruno/Rutnik partnership. Bruno's son Ken also bought a plot and built his own home there. Ken Bruno, then the District Attorney for Rensselaer County, subsequently became a lobbyist and had at least one of the same clients as Rutnik, Madison Square Garden.

It was Ken Bruno who brought the Abbruzzeses into the project and it is no doubt their ties to Bruno, who steered state funding to an Abbruzzese business, that's made these land purchases part of a criminal investigation. But Rutnik's partnership evinces a blindness on his and Bruno's part to the arm's length distance that a lobbyist and a powerful public official should have. Rutnik's ties to Bruno, former Senator Al D'Amato and Governor George Pataki helped pave the way for Gillibrand's stunning win in 2006, taking a majority Republican seat away from an incumbent, John Sweeney, disliked by GOP insiders.