Last month, the Association of Fundraising Professionals announced that T. Boone Pickens of Dallas, Texas, would receive the 2008 Paschal Murray Award for Outstanding Philanthropist at the AFP’s annual conference which is wrapping up today in San Diego.

Based on size of contributions, Pickens would certainly qualify for an award. In 2007, he ranked 8th nationally in total individual giving, behind George Soros, Sandy Weill, and Michael Bloomberg, and ahead of Eli Broad, David Koch, and Pierre Omidyar, among others, according to the Chronicle of Philanthropy . His new eponymous foundation ranks as the 5th largest single donor “hedge fund foundation,” trailing those of George Soros, Julian Robertson, Jim Simons, and Robert Wilson (and it is also smaller than the multi-donor Robin Hood Foundation founded by hedge fund magnate Paul Tudor Jones).

With billions in disposal income and a fertile mind for financial innovation, Pickens casts an increasingly large shadow over personal and corporate philanthropy. But is the impressive Pickens largesse matched with an equally impressive approach to innovative or ethical practice?

Pickens has long been an enterprising philanthropist. He attracted some notable attention in the days following Hurricane Katrina for his non-Katrina charitable generosity. At the time, the Katrina Emergency Tax Relief Act (KETRA) provided a one-time allowance for unlimited charitable giving, exceeding the usual limitation of deductions to no more than one half of a taxpayer’s adjusted gross income. Although prompted by fears of a run on charitable donations to respond to Katrina-related needs, the law did not mandate a specific Katrina connection to the incentivized giving.

Like his friends Dick and Lynne Cheney who also made some Katrina-timed donations, Pickens took advantage of KETRA to take some massive charitable deductions that didn’t have a whit of connection to Katrina assistance. He gave the golf program at his alma mater, Oklahoma State University, a cool $165 million, reportedly qualifying for the Katrina charitable giving incentive. Within minutes after receiving the donation, the OSU golf program reinvested the gift in Pickens’ own hedge fund (the golf program managers said that Pickens didn’t require that investment, it just seemed like a good idea to them). The idea must have come quickly, as the Pickens gift didn’t last an hour in the accounts of OSU Cowboy Golf, Inc. before landing in his BP Capital Management fund.

Despite Pickens’ contention that he didn’t require the golf program to invest in his hedge fund, thus ensuring that the donation was legal, he came in for strident criticism from otherwise cautious and circumspect charitable giving experts. Former IRS tax exempt unit head Marcus Owens described the OSU gift as “another case of a rich man manipulating charity for his own benefit,”, and legal expert Bruce Hopkins called it “obviously right up to the edge of what’s permissible .” Owens and Hopkins appeared concerned not only with the investment structure,