EXCLUSIVE — A Rhode Island federal judge who blocked the Trump administration’s freeze on federal assistance is under renewed scrutiny for his long-running ties to a taxpayer-backed nonprofit organization that has received millions of dollars in government grants and was flagged for serious financial irregularities.
U.S. District Judge John McConnell Jr., appointed by former President Barack Obama in 2010, issued a temporary injunction in January halting President Donald Trump’s freeze on some federal discretionary funds. The move drew praise from left-leaning legal groups — and criticism from Trump allies — because the judge served as board chairman of Crossroads Rhode Island, a 501(c)3 nonprofit organization that receives millions of dollars in public funding from the very federal agencies affected by the administration’s freeze plan.
McConnell served on the Crossroads board from 2006 to at least 2023, including a decade as chairman. During his tenure, the organization expanded its network of homeless shelters and housing programs while taking in tens of millions of dollars from federal, state, and local government sources. America First Legal, which filed a judicial misconduct complaint in May at the U.S. Court of Appeals for the 1st Circuit, shared a compilation of supporting documents exclusively with the Washington Examiner this week.
AFL’s complaint centers on what it calls a pattern of financial mismanagement and undisclosed conflicts of interest during McConnell’s long tenure on the Crossroads board. Among the most striking examples are two real estate deals in which McConnell’s nonprofit organization purchased properties from a fellow board member for far more money than the properties appeared to be worth.
According to property deeds, Crossroads purchased a building at 371 Pine St. in Providence in December 2020 for $700,000.
At the time, the property’s assessed value was roughly $410,800. The seller, Hotel Associates LLC owner Matthew Marcello, is a member of Crossroads’ board of directors. Despite that connection, the purchase was not reported as a related-party transaction on Crossroads’s 2020 Form 990, raising transparency concerns.
The organization also purchased a separate property, 94 Summer St., in January 2022 for $850,000, despite its then-assessed value of $557,400. The AFL complaint flagged both transactions as potentially problematic due to the high purchase prices and connections to one of the nonprofit organization’s board members.
The 371 Pine St. location was also tied to Rhode Island’s notorious “bribes-for-leases” scandal of the 1990s, in which former Republican Gov. Edward DiPrete and political allies were accused of steering lucrative state leases in exchange for kickbacks. The complaint pointed to overlapping ownership entities and archived news coverage linking the building to that scandal.
Meanwhile, Crossroads’s 2020 independent audit identified a “material weakness” in internal financial controls — the most serious category of deficiency, short of fraud.
Andrew Block, senior counsel for AFL, told the Washington Examiner the documents reveal that the complaint against McConnell is “well sourced in contemporary news reports, property filings, and Crossroads’ own tax filings and audits.”
“There can be no question as to the facts underlying the complaint, and it is up to the appropriate authorities to take action,” Block added.
AFL noted that the audit, coupled with the questionable property transactions, suggests systemic problems may have occurred under McConnell’s board leadership that were never disclosed in court filings.
“Despite his long-time entanglement with this federally funded organization, Judge McConnell did not recuse himself” from the case involving whether the Trump administration can cut off federal payments to nonprofits, the complaint said. “His failure to do so may violate federal law and judicial canons of ethics, raises profound concerns about Judge McConnell’s judgment as an officer of the court, and his fitness for the bench.”
Crossroads has received at least $15.4 million in federal funding from the Department of Housing and Urban Development since 2010, including over $2 million in 2025 alone, according to records cited in the complaint. Its most recent IRS filing showed that about 65% of its $28.7 million revenue came from government sources.
In New York v. Trump, McConnell ruled that the administration’s freeze of certain discretionary grants, initiated through a January memorandum by the Office of Personnel Management, lacked legal authority and threatened states’ ability to fund social services. In March, he issued a preliminary injunction that remains in effect while the case proceeds.
“The executive’s categorical freeze of appropriated and obligated funds fundamentally undermines the distinct constitutional roles of each branch of our government,” McConnell wrote in his order.
The Trump administration has since appealed. In separate litigation, the Supreme Court has already heard arguments over whether federal district courts should retain the power to issue nationwide injunctions, a legal tool McConnell used in his ruling, and the justices expect a decision soon.
The judge, who rejected a 2024 lawsuit seeking to remove Trump from the Rhode Island ballot, has now ruled against the Trump administration in three major cases. In May, McConnell blocked cuts to agencies created by Congress, including the Institute of Museum and Library Services and the Minority Business Development Agency.
He is also presiding over California v. U.S. Department of Transportation, a case brought by 20 Democratic state attorneys general challenging the administration’s threat to withhold federal transportation funds from so-called sanctuary jurisdictions. Last week, he blocked the administration’s efforts in that case.
McConnell’s long-standing ties to Democratic politics have raised additional concerns among Trump-aligned critics. Prior to his nomination to the federal bench, McConnell contributed nearly $500,000 to Democratic campaigns and causes, including $28,500 to the Democratic Congressional Campaign Committee.
His wife, Sara Shea McConnell, has also donated extensively to Democratic candidates and committees, contributing an additional $250,000, including thousands of dollars to the Rhode Island and Washington state Democratic parties. Their daughter, Catherine McConnell, worked as a senior policy adviser for the Biden administration’s Department of Education.
McConnell once chaired then-Providence Mayor David Cicilline’s campaign and previously served as treasurer of the Rhode Island Democratic Committee. He was confirmed to the federal bench by a narrow 50–44 Senate vote.
In March, Rep. Andy Clyde (R-GA) filed a resolution calling for McConnell’s impeachment, citing his board ties to Crossroads as a conflict of interest in cases affecting federal aid.
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The 1st Circuit has not indicated whether it will seek McConnell’s response or launch an inquiry.
Spokespersons for both McConnell and Crossroads did not respond to a request for comment from the Washington Examiner.
