He was once the mayor of Waterbury who ran unsuccessfully for the U.S. Senate and had his eye on a presidential appointment.

Instead, Philip Giordano has been sitting in federal prison for the past decade, serving a 37-year term for forcing the 8-year-old and 10-year-old female relatives of a crack-addicted prostitute to perform oral sex on him in various places, including a police car, his law office and City Hall.

Now, after two unsuccessful bids to overturn his conviction, vacate or reduce his sentence that went all the way to the U.S. Supreme Court, Giordano is once again trying to reverse his fate by claiming ineffective assistance at trial by his then-lawyer Andrew Bowman of Westport.

On Monday, U.S. District Judge Stefan R. Underhill will hear legal arguments on that matter before determining if an evidentiary hearing, in which Bowman and others would be required to testify, is necessary.

Such a hearing would be similar to the one recently conducted in state court for Michael Skakel.

Skakel, a Kennedy cousin from Greenwich, claimed ineffective assistance by his lawyer, Mickey Sherman, during his 2002 trial for a murder that occurred 27 years earlier.

In that hearing, Michael Fitzpatrick, a Bridgeport lawyer and past president of the Connecticut Criminal Defense Lawyers Association, was a key witness for Skakel.

But in Giordano's case, Fitzpatrick believes the former politician faces "an incredibly difficult" battle "because Andrew Bowman is a pre-eminent lawyer."

Fitzpatrick said any notion "that Phil Giordano is sitting in prison because of anything Andy Bowman did or didn't do is utterly ridiculous."

Giordano was arrested July 25, 2001, after FBI agents investigating possible municipal corruption in Waterbury heard wiretap conversations involving the prostitution of the two young girls.

At the time, Giordano was cooperating with the federal probe, which included investigating mob ties to Waterbury City Hall.