The Maroon Tiger connection

Wesley, Loadholt.

I read with interest about Willamette Weed's public records beef with the city's economic development agency, "Prosper Portland" (formerly the Portland Development Commission). In dispute is the agency's refusal to make public a report prepared by one or more out-of-town attorneys about Prosper's investment policies and procedures.

Late last year, Prosper’s newly hired executive director, Cornell Wesley, commissioned a law firm to conduct a review of Prosper’s loans, grants, policies and procedures. But the city’s economic development agency now declines to provide those reviews to WW, citing attorney-client privilege.

That’s notable because the loans by Prosper—which include smaller loans and grants but also large loans of up to $5 million for new construction, renovations and building acquisition—are taxpayer-funded. And members of the Portland City Council have repeatedly worried that Prosper, which is governed by its own board and has a separate budget process, doesn’t have the oversight to ensure it’s using money wisely and in line with the public’s desires.

The story got me to thinking, is this report really privileged? Just because a lawyer says something to a client doesn't mean it's privileged. Only communications relating to legal advice are covered by the privilege. As the American Bar Association explains:

Communications will only be privileged if the party sought, and the attorney rendered, legal advice. Because the privilege is contrary to the judicial goal of bringing relevant evidence to light, it is construed narrowly and protects only those disclosures necessary to obtain informed legal advice which might not have been made absent the privilege.

For attorneys who may counsel their clients on business matters as well as legal matters, this requirement is not always easy to meet. If the work could have been performed by an individual with no legal training, the attorney has not been consulted in a professional capacity. Thus, the privilege does not protect communications where the attorney serves the client solely as a business advisor. Under the totality of the circumstances, the attorney’s guidance must have been sought because of a need for legal advice.

As I ruminated about the Propser Portland report, wondering how the entire thing could be legal advice – surely parts of it don't contain advice of any kind – I looked a little further into the facts and stumbled upon what might be the more interesting aspect of this story.

According to the Weed, Prosper has paid two different law firms a total of $102,000 so far, with more to come for "follow-up," for this review. The firms, says the paper, are Ice Miller and Taft. Ice Miller is an East Coast firm, headquartered in Indianapolis, and Taft, based in Cincinnati, has offices all over, but none on the West Coast. It would be odd to have two law firms working on the same matter at the same time, much less two law firms so far away, but there's a simple explanation of the dual representation.

His name is Jarrod Loadholt. He and Wesley (the head of Prosper) were classmates at Morehouse College, the famed all-male historically Black college in Atlanta. Both of them got bachelor's degrees in economics from Morehouse in 2005. Wesley and Loadholt both have close ties to the young-ish mayor of Birmingham, Randall Woodfin, another Morehouse grad a couple of years ahead of them. Loadholt has been identified as a key political adviser to Woodfin, and Woodfin brought Wesley back to Birmingham, where Wesley is originally from, to run economic development there.

 Loadholt was an attorney at Ice Miller for years until last month, when he moved to Taft.

If you look at Wesley's calendar since he's gotten to Portland, you'll see that there are at least five meetings shown between him and Loadholt through the month of June 2026. One of the meetings took place just over a week after Wesley started work at Prosper, in August of last year. There seems little doubt that the reason Ice Miller and Taft were hired by Prosper is because of the connection between the two men. I can find no sign of those firms doing work in Portland at any earlier time.

To circle back to the question whether the Ice/Taft report is a public document, rather than privileged, you have to wonder how much of it was really legal advice, especially if Loadholt was the author. According to his bio on his new law firm's website, a lot of what he does seems to be about policy, lobbying, and public relations, rather than law:

He advises corporate, governmental, and nonprofit clients regarding complex legislative, regulatory, and compliance matters and collaborating with corporate, civic, and governmental executives on public affairs and political strategy across federal, state, and local policy environments. He brings nearly two decades of experience in policy development and legislative and regulatory at the federal, state, and local levels, representing clients across a range of highly-regulated industries.

But to me, the most important angle of this story is the very existence of the report. For all we know, Loadholt or his lawyer colleagues may have given Prosper some excellent guidance that will help the agency stop making atrocious policy decisions. But unless Wesley gives up the report, we'll never know.

What we do know is that the minute he took over the agency, Wesley wheeled in one of his college classmates and gave the guy's law firm a six-figure no-bid contract to do work that Wesley now claims is secret. It's not a good look.