My assessment of Decker Advertising, Inc. v. Delaware County, No. 3:23-cv-01531 (N.D.N.Y.), has changed dramatically.
I must confess that I was initially suckered in by the glamour and publicity surrounding this lawsuit, particularly the involvement of such formidable names as The New York Times, Cornell Law School's First Amendment Clinic, and Greenberg Traurig.
As a journalist and legal scholar specializing in First Amendment issues, who has personally experienced governmental retaliation for investigative journalism and criticism of public officials, I was naturally sympathetic to what appeared to be an underdog fighting governmental suppression of the press.
I thought I was rooting for the underdog.
Apparently, there was no underdog in the first place.
Recent discussions in Delaware County community groups prompted me to reconsider information that had been publicly available for years, but whose legal significance I had not previously examined in connection with this litigation.
And now the November 3, 2026 election has added an entirely new dimension.
The Prodigal Son Returns
According to the election-night results, Wayne L. Shepard has defeated Jonathan Kilday in the race for Hamden Town Supervisor.
With all precincts reporting, Shepard received 375 votes, or 61.48%, against Kilday's 231 votes, or 37.87%.
Shepard is therefore poised to return to the Delaware County Board of Supervisors.
Why is this relevant to Decker Advertising?
Because Wayne Shepard is the brother of Randy Shepard, owner of The Reporter, the newspaper whose official designation and resulting publicly funded business relationship with Delaware County are at the center of the federal litigation.
Wayne Shepard is hardly a newcomer to Delaware County government.
He spent decades in County employment, as he reported himself, since at least 1992, including senior management positions, notably as Director of the Delaware County Office for the Aging.
During those years, the County maintained business relationships with his brother's newspaper and publishing enterprise.
Indeed, Wayne Shepard's own deposition testimony addressed expenditures by his department for printing services through his brother's business.
The familial relationship, the governmental positions, and the public expenditures are not recent discoveries.
What has changed is their immediate significance to the prospective judicial relief being sought in federal court.
The prodigal son is returning to the County's governing body, while his brother's business is asking a federal judge to order the County to restore a publicly funded relationship with that business.
This raises a rather interesting question of New York municipal law.
Is This Really a First Amendment Case?
Decker Advertising has presented its dispute with Delaware County as a First Amendment retaliation controversy.
But the First Amendment does not confer an entitlement to receive municipal business.
Nor does the constitutional protection of freedom of the press automatically create a right to a particular publicly funded governmental designation.
In my revised assessment, the fundamental issue is whether the County was legally authorized to maintain the disputed business relationship in the first place, given the longstanding familial relationship between the newspaper's ownership and a senior County official.
I believe Delaware County should have addressed that question at the outset.
Instead, the litigation has proceeded for years, generating legal expenses while the controversy has been framed predominantly as a dispute over freedom of the press.
Now, with Wayne Shepard's return to the Board of Supervisors, the conflict-of-interest question becomes prospective as well as historical - and front and center of that litigation.
The federal court is being asked to grant relief that would operate upon the County's future governmental and financial arrangements.
That makes the legality of the requested relief an independent question.
Enter the Delaware County Taxpayer
New York General Municipal Law Article 18 regulates municipal conflicts of interest, while General Municipal Law § 51 provides a statutory mechanism for certain taxpayer challenges to unlawful municipal conduct and expenditures.
The official newspaper designation is expressly addressed within New York's municipal conflict-of-interest statutory framework, including the definition of municipal contracts and the specific exception for authorized newspaper designations.
Those provisions require careful statutory analysis, particularly concerning the distinction between an official's financial interest, a familial relationship, participation in governmental decisions, and the validity of the resulting municipal arrangement.
But there is another question, and it is procedural.
Could a Delaware County taxpayer (including yours truly) seek to intervene in Decker Advertising v. Delaware County on the side of the defendant County itself?
Federal Rule of Civil Procedure 24 permits intervention under specified circumstances, including where an applicant claims an interest relating to the subject of the action that may be impaired by its disposition and is not adequately represented by existing parties.
A taxpayer seeking to prevent potentially unlawful future expenditures could examine whether the requested reinstatement implicates such an interest.
The proposed intervention would not necessarily concern whether Decker Advertising suffered First Amendment retaliation.
It could instead concern whether the federal court should grant prospective injunctive relief compelling a municipality to resume a publicly funded arrangement affected by a renewed conflict-of-interest question.
That is a distinct legal issue.
An Unexpected Procedural Alliance
And here comes the particularly interesting part.
The defendant Delaware County is represented by attorney Frank W. Miller.
I have litigated against Miller in several proceedings and have publicly criticized his litigation conduct, or rather, his constant procedural sloppiness, lack of readiness and constant attempts to substitute the law for claims of privileges from various judges - which sounds really dirty when you consider that Miller's managing partner at his present law firm Hancock Estabrook LLP is brother to the Chief Administrative judge of Upstate New York - who is obviously in charge of assigning those same judges to our cases.
And, I am suing his client Delaware County for a variety of constitutional violations.
Nevertheless, the possibility of intervention on the side of his client, that same Delaware County, deserves serious consideration here.
Not that I am particularly looking foward to any alliances with Mr. Miller or his client - brrr, no.
But, after all, the legality of prospective public expenditures takes priority over my personal feelings as to how VERY sloppy is the attorney chosen by the current County government to represent them in court.
Nor must a taxpayer (yours truly) share every position taken by the County's counsel to oppose a particular form of judicial relief.
I am therefore examining whether Delaware County taxpayers could qualify for intervention under Rule 24, including whether the existing parties adequately represent their interests in the legality of future municipal expenditures.
As a Delaware County property owner and taxpayer, I know I qualify for that role, too.
Whether I or any other taxpayer will actually pursue intervention remains an open question.
For now, I find the legal possibility sufficiently interesting to warrant examination.
And I find the prospect of a taxpayer intervening on the side of Delaware County, represented by Frank Miller, particularly ... amusing.
The Question Before the Federal Court
The November 3 election results have brought the familial relationship between the newspaper's ownership and County government into renewed focus. Not counting the fact that the Town of Hamden happens to also employ Wayne Shepard's sister as the Town Clerk and gives business to his same brother Randy Shepard's newspaper as publisher of the Town's legal notices. A family-owned town... the local cuteness overload.
So, now the $3,999,999,999.00 Decker Advertising question is no longer confined to what occurred years ago.
It concerns what the County may lawfully be compelled to do in the future.
Can a federal court order prospective restoration of a publicly funded municipal designation without addressing a substantial question concerning the legality of that FAMILY arrangement under New York municipal law?
Can a County taxpayer seek to participate in the proceedings to raise that issue?
And if the existing parties have not adequately addressed the taxpayers' interests, might Rule 24 provide a procedural avenue for doing so?
These are questions worth exploring.
Sometimes the most unexpected ally of a municipal defendant is a taxpayer who has spent years litigating against that very municipality.
And sometimes a lawsuit promoted as a grand First Amendment controversy, so advertised with great fanfare across the nation by New York Times, Cornell Law School's 1st Amendment Clinic and Greenberg Traurig (who used the opportunity, at Delaware County taxpayers' expense, to teach their new recruits in battle how to do electronic discovery) deserves a second look through the considerably less glamorous lens of municipal contracts, conflicts of interest, and us, the taxpayers who finance them.
To be continued, perhaps. After a conference with Mr. Miller. Not likely.
Had he agreed to such a conference, I would have asked the $5,000,000,000,000.00 question: WHY DIDN'T YOU RAISE THAT CONFLICT IMMEDIATELY? YOU COULD HAVE SAVED DELAWARE COUNTY TAXPAYERS ZILLIONS OF DOLLARS!!!!! MILKIN' THE CASE MUCH, HUH?




