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, but with the fact that Pickens served on the board of OSU Cowboy Golf.

While the recipient account may read “golf,” it services other OSU athletic issues. The Pickens gift was apparently intended for improvements to OSU’s Boone Pickens Stadium and construction of housing for athletes as well.

Some of us also remember other aspects of the Boone Pickens philanthropy, including his $3 million to the Swift Boat Veterans and POWs for Truth 527 plus a $1 million pledge to anyone who could disprove any element of the Swift Boat charges. After Kerry accepted the challenge, apparently Pickens changed some of the terms, likening his modifications of the challenge to betting in poker, making it doubtful that Pickens ever paid up.

Along with builder Bob Perry who was a major funder of the Swift Boat 527, Pickens has also been charitably generous to another 527 called “Stop Her Now”, aimed at the “radical leftist agenda” of candidate Hillary Clinton (according to the organization’s website banner). The octogenarian investor king generally makes profitable economic moves, maintaining him among the top 500 richest people in the world, but his political choices don’t always pay off, notably banking on Rudy Giuliani to win the Republican presidential nomination this year.

In 2006, Pickens announced the formation of the T. Boone Pickens Foundation, started with a $135 million capital infusion. The president of the foundation, Ronald D. Bassett, and the vice president, Robert L. Stillwell, are two thirds of the management team of BP Capital Management, Pickens himself completing the investment triumvirate. Designed to close by the time he dies, the Foundation adheres to the investor’s concept of “performance-based philanthropy,” reportedly an idea shared by his friend, right wing oilman and philanthropist Charles Koch, part of Pickens’ strategy of “changing the face of philanthropy.” Blending corporate and philanthropic identities may be part of that changing face: the Foundation’s 2006 990PF showed an end-of-the-year investment of $110 million in Suncor Energy, not much different than BP Capital Management’s holdings of $197.4 million worth of Suncor stock as of the end of the 4th quarter of 2007.

The Foundation’s 2006 990PF listed $26.3 million in grants, including $5 million to the University of Texas, $5 million to the Texas Woman’s University (toward the construction of the T. Boone Pickens Institute of Health Sciences), $6 million to Johns Hopkins Hospital, and $8 million to Big Brothers and Big Sisters in Dallas. The Foundation’s website lists other organizations that have received grants, though without specific grant information, including the Center for Missing and Exploited Children, Meals on Wheels, and the Special Olympics of Texas.

Joining Pickens on the AFP honor roll will be Wal-Mart and Sam’s Club receiving the Freeman Philanthropic Services Award for Outstanding Corporation, like Pickens exceptionally generous with charitable check-writing (Wal-Mart usually ranks as the nation’s largest corporate philanthropist in terms of cash giving). There are people, particularly in rural and small town America, who will swear by the local charitable giving of their regional Wal-Mart, but the timing of the AFP award coincides with the roll-out of Wal-Mart’s new strategic giving strategy—a shift from largely local grants to community-based organizations such as boy scouts and girl scouts to a more national, strategic approach keyed to the issues of healthcare, environmental sustainability, and education and training for 12- to 30-year-olds, the first two obvious themes in Wal-Mart’s recent politically sensitive rebranding efforts.

As an organization devoted to fundraising and fundraisers, AFP has strong incentive to honor individual and corporate donors with active charitable checkbooks. But charitable giving and philanthropic grantmaking, when practiced by the likes of Boone Pickens no less than Wal-Mart, have political and ideological dimensions that may not always warrant nonprofit sector accolades.