Two principal business organizations bestowed their political stamps of approval on the mayoral contenders this week.

The Greater Washington Board of Trade endorsed the re-election of Mayor Adrian Fenty; the D.C. Chamber of Commerce gave its support to Council Chairman Vincent Gray, the challenger.

No great surprises here. But what took place behind closed doors spells more trouble for the incumbent. And these endorsements and others signal more fundamental problems for Fenty as he seeks to dig out of the hole he's dug for himself.

Fenty's appeal to both business groups was similar: He asked to be treated as if he were a chief executive officer with his contract up for renewal. He listed his accomplishments and said he had earned another four years. Sounds reasonable.

Last election season, the Board of Trade endorsed Fenty's opponent, Linda Cropp. It was one of many establishment, old-guard interest groups that feared the unknown young council member. You can't get much more established than the Board of Trade. Why did the corporate types back Fenty this time around?

Process, which Fenty despises, may have saved his cookies. In years past, the Board of Trade's regional political action committees have heard the candidates' pitches and made the endorsement. But this year, for the first time, the board's executive committee passed judgment and gave its stamp of approval.

"If we are a regional organization," Board of Trade chief Jim Dinegar told me, "we have to bring a regional mind-set."

Fair enough. But had the board stuck to the long-standing practice of having the D.C. political action committee endorse, there's a good chance it would have gone for Gray. Which brings me to the Chamber of Commerce.

The chamber's members are much more focused on business within the District. They are the ones who have to deal directly with the government, the mayor's appointees and his bureaucrats. Their endorsement is much more telling. Fenty understands this. That's why he dispatched his political henchmen and top appointees to phone some of the chamber's political committee members.

My sources say John Falcicchio, Fenty's campaign fundraiser and manager, personally called to lobby for the chamber's imprimatur. Can you say strong-arm? No dice. Despite the pressure, the chamber's political committee could not be brought to heel. The members threw their support behind Gray.

The Board of Trade's endorsement is a nice pat on the back, but it's not worth much, really. It doesn't bring cash; most of its members live in the suburbs and don't vote in D.C.

The chamber's stamp packs more punch, in dollars and votes. It also signals a change in the fear factor. Many of the chamber's members had told me they feared Fenty's retribution if they went against him or spoke on the record about what they considered to be his cronyism in contracting.

I guess the fear is gone.

Harry Jaffe's column appears on Tuesday and Friday. He can be contacted at ">