Might it hurt Rajat Gupta to get sentencing support letters from the 1%?

The question in the title of this post is prompted by this notable new article in the Wall Street Journal headlined "Dear Judge, Gupta Is a Good Man: Bill Gates, Kofi Annan Among Those Writing in Support of Inside Tipster Ahead of His Sentencing." Here are the story basics:

Rajat Gupta, the former Goldman Sachs Group Inc. director convicted of insider trading, has lost his powerful spots on corporate boards, his reputation and likely his freedom when a judge sentences him later this month. But Mr. Gupta, 63 years old, still has plenty of powerful backers, including Bill Gates and Kofi Annan, and they are lining up to support him with letters to the judge.

Mr. Gates, co-founder of Microsoft Corp., and Mr. Annan, former secretary-general of the United Nations, are among those who have written letters to U.S. District Judge Jed Rakoff on Mr. Gupta's behalf. More than 200 letters have been sent to the judge through Mr. Gupta's lawyers ahead of the Oct. 24 sentencing, according to the submissions, which were examined by The Wall Street Journal....

Mr. Gupta was convicted in June of giving hedge-fund manager Raj Rajaratnam, his friend and business associate, inside information about Goldman's financial results and an investment by Berkshire Hathaway Inc.'s Warren Buffett during the financial crisis. Prosecutors said Mr. Rajaratnam's hedge fund made millions based on Mr. Gupta's tips, while Mr. Gupta, also a former director at Procter & Gamble Co., benefited from the leaks because of their friendship and mutual business interests.

Prosecutors are likely to argue that federal sentencing guidelines dictate a term for Mr. Gupta that could exceed 10 years, based on the illicit trading gains by Mr. Rajaratnam's fund. But the guidelines are advisory, and Judge Rakoff usually hands down less than they suggest....

Mr. Gupta, the former head of McKinsey & Co., the global corporate consulting firm, was active in the philanthropic and charitable communities in the U.S., in his native India and other countries. Letters from his supporters include those from leaders of companies, academics and Wall Street figures. His family also wrote to the judge, including his wife, four daughters and an 84-year-old aunt in India....

It is common for defendants to ask friends, family and prominent figures they may have encountered in their lives to write letters on their behalf to the court ahead of sentencing. Defense lawyers routinely cite such letters at sentencing in hopes of providing a fuller picture of a defendant beyond the crime they've been convicted of committing, particularly when it comes to a defendant's charitable works....

Mr. Gupta's submissions include letters from a class of luminaries not often seen at sentencing, but reflective of those he associated with as a top executive at McKinsey and through the philanthropic causes he supported.

In prior posts and comments, there has been an interesting and robust discussion about whether and how character letters from family, friends, and colleagues can play a role in post-Booker federal sentencing decision-making.  In this case, as the question in the title to this post suggests, I cannot help but wonder if the very high-profile nature of the folks writing on Gupta's behalf could, directly or indirectly, risk creating the impression that Gupta's extraordinary prominence and connections provide a special reason not to give him any kind of special break at his federal sentencing.

Related posts on upcoming Gupta sentencing:

• Any early federal sentencing predictions after quick conviction in Gupta insider trading case?
• Interesting commentary on upcoming Gupta sentencing for insider trading
• Rajat Gupta hoping to get by (federal sentencing) with a little help from his friends
• Gearing up for high-profile sentencing of high-profile insider trading defendant