First, your points about prior offenders reintegrating themselves and such are both well-said and correct.  But, Asher is not one of the folks who just looks to keep a regular job after paying their debt to society.  And, IMHO a cursory or dismissive treatment of the Asher-Giuliani relationship may well overlook both character and judgment flaws in Rudy, and insights into the pay-to-play world he promises his wealthy contributors.  Which, I suppose, is a reason for bringing F. Lee Bailey (whose last appearance the vast majority of people will remember was in "OJ, The First Trial") into the story - pure irrelevancy.

The Vanity Fair article linked to earlier today devotes a good chunk of its pages 2 and 3 (of 7) to Giuliani and Asher.  Excerpted from the article:

Giuliani also failed to disclose his consulting contract with a Florida entrepreneur named Hank Asher when in 2004 he talked about him to a magazine writer who was profiling Asher. In fact, the writer was this writer, and the magazine was Vanity Fair.

Asher was, and remains, a complicated, fascinating character. ...

[He was the guy who first put together "Matrix" (remember that privacy-destroying system?) and later "Accurint". ]

After 9/11, Asher had interested the Bush administration and numerous state law-enforcement agencies in acquiring Matrix. He had a problem, though: in his youth, he'd been a cocaine smuggler. Asher had come clean, and gone so far as to help the D.E.A. stop other traffickers. But if he was going to interest the government in his system, he needed some very heavy character references. Who better than Rudy Giuliani? (my emphasis)

"The first time I met him, he did a demonstration for us at my office," Giuliani told Vanity Fair after Asher casually suggested the ex-mayor might talk about him. "When I saw it I immediately realized that this was a technology that would have been very helpful to us even when I was the mayor and putting together programs for reducing crime to help us find serial killers, abductors of children, and of course terrorists." Giuliani knew all about Asher's sketchy past, but he was all right with it.

No mention was made, either by Giuliani or by Asher, of the contract Giuliani Partners had signed with Asher to promote Asher's company, Seisint.

...

According to an affidavit filed by an outraged Seisint shareholder and reported by The Washington Post, the contract that Asher basically rammed through his board of directors in December 2002 called for Seisint to employ Giuliani Partners for two years at a fee of $2 million a year. Giuliani Partners also received 800,000 warrants with an exercise price of $10. The shareholder's affidavit declared that Seisint had received no financial benefit from the contract. (Both sides later agreed to settle the suit.)

[(Ultimately) Reed Elsevier, the global information company that owns LexisNexis, bought Seisint in July 2004 for a reported $775 million.]

The Seisint story demonstrated another Giuliani approach: working for warrants, which allow the holder to buy stock at a specified price any time before a specified date. The ex-mayor knew better than anyone the value of his name to companies trying to raise money or go public or score a big sale. Some of the publicly traded companies were penny stocks, trading for less than five dollars a share. ... Working for warrants had its downside, though. It put Giuliani in business with typical denizens of the penny-stock world--dreamers and the occasional scam artist--flogging long shots. It also put the ex-mayor in the position of appearing to sell his name and endorsement for cash.