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In his first year atop Prosper Portland, the new executive director of the city’s economic development agency has signed three no-bid contracts totaling $456,000 with two out-of-state college friends. The agency will not disclose even a scope of work for two of the three contracts, citing attorney-client privilege.
Cornell Wesley took the reins at Prosper Portland in August 2025. Hailing from Birmingham, Ala., where he served as the city’s chief economic development officer for nearly five years, Wesley moved cross-country and took the helm of Prosper as the agency sought to regain public confidence.
“I am confident that he brings the expertise and insight that Portland needs in this moment,” Mayor Keith Wilson said when he announced Wesley’s hiring. “Working together, we can revitalize our economy and realize an economic renaissance for Portland.”
But WW has learned through public records requests that since joining Prosper, Wesley has awarded three no-bid contracts to two of his college friends, both of whom live thousands of miles from Oregon. The three contracts, two of which remain active, are collectively worth $456,000. As of late September, the agency had paid out roughly $264,000.
The contracts raise two problems. The first is who got them: Wesley steered public money to longtime friends without competition, using an exemption he himself approved for one of them. The second is what Prosper won’t say. An agency still recovering from a botched $7 million loan and a reckoning over urban renewal hired Wesley, who promised more accountability. Yet it has refused to tell taxpayers what they’re buying, invoking attorney-client privilege to shield even a basic description of work.
Prosper has repeatedly declined to provide even a high-level summary or scope of the work conducted under two of the contracts, citing attorney-client privilege. Wesley signed a $132,000 contract with an Indianapolis law firm called Ice Miller in December 2025; a now-$165,000 contract with Synergy Credit Union Consulting, a Chicago-based LLC this March; and a $132,000 contract with a Cincinnati-based law firm called Taft in June.
Wesley signed all three contracts without seeking board approval, which Prosper says is within the executive director’s authority. And although one of the contracts would normally be subject to the agency’s competitive procurement process, records obtained by WW show that Wesley approved an exemption that allowed the agency to bypass that process.
Prosper maintains that Wesley acted aboveboard and followed all procurement and contract policies laid out under state law and Prosper policy. The agency and Wesley have maintained that the contracts pose no ethical issues.
“Part of the mandate I was given was to review our programs and procedures and if improvements were needed, make the required changes to ensure this agency serves the city and its residents,” Wesley said in response to questions from WW. “Once I started my review, I shared with [board chair Gustavo] Cruz, board members, and Prosper Portland staff that, from previous roles I had held, I knew individuals or firms that could provide a fresh perspective, bring in best practices and understandings from other states and nationally, and make the recommendations on system improvements necessary.”
But two city councilors say Wesley’s conduct is concerning and warrants greater scrutiny.
“On its face these facts are concerning,” said Council President Jamie Dunphy. “And even if the contracts are technically ethically all aboveboard, it contributes towards a narrative that’s deeply unhelpful. Prosper should do everything in their power to lean into public accountability, and not just follow the strict letter of the rules.”
When Wesley joined Prosper Portland last fall, the city of Portland touted his leadership for bringing in $1.2 billion in new growth investments to Birmingham.
Prosper was under scrutiny when Wesley arrived. The agency was dealing with a $7 million loan gone wrong to a shoe manufacturing startup. Its former executive director had just lost his job after publicly battling with two city councilors who tried to strip the agency of $11 million annually in general fund dollars.
Perhaps more importantly, the agency was years deep into an identity crisis. Urban renewal had fallen out of favor due to the gentrification to which it contributed—most acutely in historically Black neighborhoods.
For those reasons and more, the new Portland City Council turned a critical eye on Prosper. Unlike most city agencies, Prosper does not fit neatly under the administrative structure. An independent board of commissioners appointed by the City Council sets Prosper’s annual budget and takes votes on loans, grants and other major policy decisions. That arm’s-length relationship bothers some city councilors who want tighter city supervision.
At the council’s Finance and Government Committee of the Whole on July 23, Wesley told city councilors he had quickly realized the agency needed greater accountability. He described how he had sprung into action. “Immediately, I audited every programmatic lane in Prosper. Every grant, every loan, every policy and procedure have been audited,” Wesley said.
But soon after, Prosper would decline to provide any information about the contracts Wesley had described to WW, citing attorney-client privilege. Now, documents obtained through a public records request shed light on those very contracts—and Wesley’s unusual procurement decisions.
The first contract Wesley awarded was to Ice Miller, a Indianapolis, Ind., law firm. A heavily redacted copy of the signed contract, dated Dec. 3, 2025, in an amount up to $132,000, shows the principal lawyer on the project is Jarrod Loadholt, whose hourly rate is listed at $880. Loadholt attended Morehouse College with Wesley in Atlanta; they both graduated in 2005, according to their LinkedIn profiles.
Prosper Portland employs its own in-house legal team, which makes the hiring of outside counsel notable in itself.
Prosper redacted all details of the nature of the work included in the contract. Prosper spokesman Shawn Uhlman, prior to the agency releasing the contracts to WW, said that “several attorneys and support personnel worked on the project” when asked if there was a primary lawyer on the project. But the contract makes it clear that Loadholt is the lead attorney. “I will be the primary contact as to this relationship with Ice Miller LLP,” the contract, signed by Loadholt, states. “Any questions or concerns that may arise in this regard may always be directed to me.”
Then, in March, Wesley brought on another of his friends. Wesley awarded a contract to Chicago-based Synergy Credit Union Consulting. The principal and founder is a man named Ancin Cooley. Wesley and Cooley had three years of overlap at Morehouse College and were in the same fraternity, according to their LinkedIn profiles and social media accounts.
The original contract signed by Cooley and Wesley on March 16 is for $85,000 for “lending infrastructure and credit risk management consulting services.” (One of Prosper’s lines of business is lending money to companies that have struggled to obtain commercial financing.)
It was set to expire on Sept. 1. But two extensions made the total contract worth $165,000 through December 2026. Wesley signed the first extension. The second extension is signed by Lisa Pettinati, Prosper’s director of real estate and community development, under the “delegated authority” of Wesley.
Cooley wrote in a letter attached to the contract that Synergy would provide a “comprehensive four-phase engagement—from diagnostic assessment through design, implementation, and ongoing advisory—to build a lending operation that is disciplined, compliant, scalable, and aligned with Prosper Portland’s community impact goals.” In a document titled “understanding of needs” attached to the contract, Cooley wrote that Prosper is “deploying significant public capital without the institutional lending controls that any regulated financial institution would consider foundational,” a weakness that poses “reputational risks to the City of Portland.”
Synergy was listed as “not in good standing” with the Illinois Secretary of State’s Office as of early October, but on Oct. 12—the same day WW reached out to Cooley with questions about the company’s status—records show that Cooley submitted the LLC’s annual filing, restoring its active status. He did not respond to WW’s questions.
Because Prosper hired Synergy for nonlegal work and the contract amount exceeded the procurement threshold of $25,000, the contract would normally be subject to Prosper’s procurement rules. But, it turns out, Wesley approved an exemption that allowed Synergy to bypass that process.
The exemption form, a copy of which WW obtained through a public records request, says, “Synergy’s unique background and experience reduce the practical availability of comparable providers.” (Synergy’s website states that it is “singularly focused on serving credit unions.” Yet a business filing with the Illinois Secretary of State’s Office shows that Cooley petitioned to change the name of the business to Synergy Economic Development Consulting on March 2—just two weeks prior to receiving the Prosper contract.)
The exemption form states that if anyone who signs it “has an actual or potential conflict of interest with the Consultant, as defined in Prosper Portland’s policy on Conflict of Interest, they must confer with Prosper Portland’s Chief Conflicts Officer before acting on this request.”
Uhlman says no conflict of interest exists for Wesley, so Wesley did not have to disclose any conflict of interest. Indeed, there is no indication that Wesley stood to financially gain from the contracts or has family ties to the recipients. However, Uhlman says, although Wesley did not disclose his friendship to the two men formally in writing, “at multiple points throughout the process executive director Wesley mentioned and acknowledged having worked with the firms/individuals.”
Wesley says Cooley has visited Portland three times and billed Prosper $1,882 for travel costs.
Prosper did not respond to a question about Wesley’s friendship with Loadholt and Cooley, but has confirmed that Wesley “worked with” them “in previous roles.” (Law professor and political commentator Jack Bogdanski first noted Loadholt’s connection with Wesley after reading WW’s Aug. 9 story about the reviews.)
Prosper signed a contract with another law firm, Taft, in June. Taft has offices in 14 cities. None is on the West Coast.
Similar to the Ice Miller contract signed five months prior, the contract was for 12 months for an amount up to $132,000. The contract is also heavily redacted. The lead attorney under the contract, documents show, is Loadholt, who had left Ice Miller earlier that month and joined Taft.
Loadholt signed the contract, and so did Wesley, on June 12. Ice Miller’s work had informally ended less than two weeks prior, on May 31. Although both contracts with law firms involve the same lawyer, Prosper initially claimed they are not connected. “Ice Miller completed its scope,” Uhlman said in a Sept. 29 email. “Taft is working under a different contract and scope.”
But Uhlman would later say that the Ice Miller contract extension “guarantees a smooth transition and sharing of information” between the two law firms.
“As the work with Ice Miller wound down and we looked at an additional scope, it made sense to continue the working relationship with Jarrod and his team, despite their move to a new firm,” Wesley said. “I believe their familiarity with the agency enabled them to immediately focus on the work at hand with almost no time needed to get up to speed.”
Prosper has repeatedly declined to share any of the work product from the contracts to describe their value to Portland taxpayers, citing attorney-client privilege—even though Prosper early on explicitly said the law firms were performing “programmatic reviews.” (Wesley would later write that programmatic reviews are legal work.)
Alan Kessler, a Portland lawyer who specializes in public records, says that Prosper’s claim of attorney-client exemption may be improper.
“Unless this was either prepared by or for a lawyer in anticipation of litigation or was a ‘confidential communications made for the purpose of facilitating the rendition of professional legal services,’ the exemptions they are claiming are probably inapplicable,” Kessler says.
Neither the Taft or the Ice Miller contract went in front of the Prosper Board of Commissioners for approval. That’s because the agency as of a 2024 policy change gives the executive director the authority to approve contracts without board approval under $500,000.
Neither of the law firm contracts went through Prosper’s competitive bid process, either. That process mandates that Prosper invite at least three vendors to respond to a solicitation for any contract in excess of $25,000. Prosper says that’s because “contracts with attorneys are exempt per state law and existing Prosper Portland policy.”
Prosper board chair Gustavo Cruz said in a statement that the “engagements were all handled in accordance with Prosper’s policies and procedures” and that the board has “received updates from Cornell and staff regarding the work performed.” He did not respond to a question about whether or not the board was made aware that Wesley was friends with the consultants.
Other board members WW contacted did not respond substantively to questions about the contracts, but did not appear to be aware of Wesley’s friendship with the two men.
City Councilor Olivia Clark says that details of the contracts are concerning, and provides yet another reason for why the city should have greater oversight over Prosper.
“On the surface, it doesn’t look good,” Clark says. “I think this is another reason we should bring them under the wing of the city for greater scrutiny.”
