Draft for “Bridles and Bootleggers” - May 21

Dan Forbush

Last updated May 5, 2026 6:37pm

After-Dinner Remarks

Bridles and Bootleggers: Saratoga at the Edge of Respectability

Greg:

I can improve on this substantially if you decide you'd like to include more on Finley in your remarks.

Dan

Good evening, everyone—and thank you. After a dinner like that, I promise not to keep you too long, but I do want to take you back for a little while to a Saratoga that may feel both familiar and slightly unsettling. Because if there is one place in America where elegance, sport, money, and something a bit more shadowy came together in a uniquely visible way, it was right here in Saratoga Springs in the 1920s. This is a story about that intersection—and about the moment when a city had to decide what it was willing to be known for.

To understand Saratoga in 1926, you have to hold two images in your mind at the same time. On the surface, everything looked exactly as it should. The racing season was in full swing. The grandstand was filled with well-dressed crowds. Visitors arrived in motorcars, and increasingly by airplane, bringing with them wealth, expectation, and a sense that Saratoga was still one of the great resort destinations in the country. There was a rhythm to it all—the races in the afternoon, dinners in the evening, the social whirl that gave the place its enduring charm. This was the Saratoga that people came to see and to be part of, and it was very real.

But alongside that Saratoga—sometimes just beneath it, sometimes not beneath it at all—was another reality that was just as real and far less discussed in polite company. Gambling was not merely present; it was thriving. Bookmaking, pool selling, card games, roulette—these were not hidden in remote corners or carefully concealed from view. They operated with a degree of openness that, even at the time, struck observers as remarkable. One account from the investigation that followed would note that these activities were so widely known that “even the children on the streets knew” where they were taking place. That line has a way of staying with you, because it captures the essential truth: this was not a secret system. It was a visible one.

And that raises the obvious question—how does something like that continue? The answer is not mystery; it is accommodation. Saratoga’s economy depended on the racing season, and the racing season drew people who were interested not only in horses, but in risk, excitement, and the chance to wager. The money flowed, businesses benefited, and over time a kind of understanding took hold. It was never formally declared, but it was widely recognized: certain things would be allowed to continue, so long as they did not create too much disruption. Laws existed, of course, but enforcement could be… selective. It was, as people sometimes describe such arrangements, a matter of looking the other way. A wink, more than a confrontation.

For a time, that arrangement worked. Saratoga prospered. Its reputation held. Visitors continued to come, and the city maintained its place as a premier destination. But arrangements like that carry within them a kind of instability. They depend on discretion, on shared silence, on the idea that what everyone knows does not have to be openly acknowledged. And eventually, someone decides to break that silence.

In Saratoga’s case, that someone was a man named Peter A. Finley. He was not a figure of great political power. He was not a headline name. He was, instead, the president of the Saratoga Taxpayers’ Association—hardly the sort of position that typically reshapes a city’s trajectory. But Finley did something that, in its simplicity, proved enormously consequential. He wrote a letter.

He wrote to Governor Alfred E. Smith, and in that letter he did not hedge or soften his language. He described what was happening in Saratoga in terms that made it impossible to dismiss as rumor or exaggeration. Gambling was open. The laws of the State of New York were not being enforced as they should be. And if nothing were done—if the situation were allowed to continue—it would reflect not only on Saratoga, but on the State itself. There was an implicit challenge in that letter, and it was a powerful one: Would the laws of New York be applied consistently, or would Saratoga remain an exception?

That letter changed everything, because it moved the issue from local understanding into public accountability. Once the question had been put to the Governor in that way, it could not easily be ignored. It was no longer a matter of local custom or economic convenience. It was a test of whether the State would act.

Governor Smith understood that. He also understood that how he responded would matter as much as whether he responded. Rather than issuing statements or making immediate accusations, he took a different approach—one that shifted the entire conversation. He appointed a judge, Christopher J. Heffernan, to conduct a formal investigation. That decision transformed the situation overnight. What had been talk became testimony. What had been widely known became formally examined. And what had been tolerated was now subject to legal scrutiny.

The investigation that followed confirmed what many already understood, but had not been required to prove. Gambling operations were widespread and visible. They functioned with a degree of openness that suggested not merely occasional lapses in enforcement, but a consistent failure to act. The officials responsible for upholding the law—those with the authority to intervene—had not done so in any meaningful way. And when the moment came for them to respond, to explain, to defend their actions, they largely declined. That silence became, in its own way, part of the record. Because in a setting like that, silence does not go unnoticed. It raises its own set of questions.

The conclusions of the investigation were clear and difficult to dispute. The failure to enforce the law had not been incidental. It had been sustained. And it had allowed a system of illegal activity to operate openly within the city. At that point, Governor Smith had before him not speculation, but evidence. The actions that followed were decisive, and they marked a turning point in Saratoga’s relationship with the law. The idea that the city could operate indefinitely under a separate set of expectations—that it could remain “wide open” without consequence—was no longer tenable.

Now, it would be easy to tell this as a story with a clean ending—a moment of exposure, followed by reform, followed by a permanent return to order. But history rarely cooperates with that kind of simplicity. What makes the Saratoga story so compelling is what happened next—or, more precisely, what happened not long after. Only a few years later, the very Commissioner of Public Safety whose failure to enforce the law had been laid bare by the Heffernan investigation was elected once again by the people of Saratoga Springs.

That detail has a way of complicating the narrative, and in the best possible way. Because it reminds us that communities are not static, and they are not always consistent. The same city that demanded accountability in one moment may, in another, choose familiarity over reform. Public memory fades. Priorities shift. Relationships endure. And the balance between principle and practicality is renegotiated, again and again.

What that tells us is not that the events of 1926 were meaningless. On the contrary, they were profoundly important. But they were not final. They were part of an ongoing process—a cycle of recognition, action, adjustment, and, sometimes, reversal. The people of Saratoga in that era were not simply right or wrong, virtuous or compromised. They were navigating a set of realities that included economic dependence, social ties, and differing views of what mattered most. In that sense, they were not so different from us.

And that is why this story still resonates. Because at its heart, it is not really about gambling. It is about the choices that communities face when their values and their interests come into tension. It is about the moment when something that has been

By 1926, Saratoga had reached that threshold.

The city’s economy depended heavily on the racing season. Hotels filled, restaurants thrived, and the flow of money—legal and otherwise—sustained livelihoods. To disrupt that system risked economic backlash. Yet to ignore it invited a deeper erosion: the perception that the rule of law itself was negotiable.

The tension between those realities created a jurisdictional fault line. Local authorities had incentives to maintain the status quo. The state, by contrast, had a mandate to enforce its laws uniformly. Saratoga became the testing ground for that conflict.

At the center of it stood Governor Alfred E. Smith.

The Finley Letter: Forcing the Governor’s Hand

The immediate catalyst for state intervention did not come from Albany. It came from Saratoga itself.

Peter A. Finley, president of the Saratoga Taxpayers’ Association, understood both the power of public accusation and the vulnerability of political leaders to implication. His letter to Governor Smith was not simply a complaint. It was a strategic document—crafted to compel action by framing inaction as complicity.

Finley’s approach was direct, even provocative. He alleged not just the existence of illegal gambling, but the expectation that the Governor would delay any meaningful response until the racing season had run its course. The implication was clear: that Smith would prioritize political relationships and economic convenience over enforcement.

The letter advanced three interlocking claims.

First, that any investigation would be deliberately postponed—allowing gambling interests to profit uninterrupted through the summer months.

Second, that the Governor’s relationship with Saratoga’s Commissioner of Public Safety, Arthur J. Leonard, constituted a conflict of interest. By invoking “friendship,” Finley suggested that enforcement decisions might be shaped by personal loyalty.

Third, that Smith would actively protect local officials and associates involved in or benefiting from the gambling economy.

These were not subtle insinuations. They were designed to corner the Governor publicly.

If Smith did nothing, the accusation would stand: that he had chosen political convenience over legal duty. If he acted, he would have to do so in a way that disproved not only the charges themselves, but the broader narrative of complicity.

The letter transformed a local issue into a test of executive integrity.

Smith’s response would define his governorship.

III. The Governor’s Calculus: Politics, Law, and Credibility

Governor Smith faced a complex decision environment.

He was not an outsider to New York’s political realities. As a product of Tammany Hall, Smith understood the mechanics of political alliances, the importance of relationships, and the delicate balance between enforcement and pragmatism. Saratoga’s situation would not have surprised him.

What made the moment different was visibility.

The allegations were now public. The narrative was being shaped in real time. And the stakes extended beyond Saratoga. Smith’s credibility as Governor—and as a national political figure—was on the line.

He needed a response that would accomplish several objectives simultaneously:

Establish that the state would enforce its laws, even against entrenched local practices
Demonstrate independence from political allies or perceived allies
Ensure that any findings would withstand scrutiny, both legal and political
Avoid the appearance of arbitrary or politically motivated intervention

The solution Smith chose was procedural rather than rhetorical.

He would not argue the case publicly. He would investigate it.

And crucially, he would do so through a figure whose authority derived not from politics, but from law.

The Appointment of Christopher J. Heffernan

Smith’s selection of Justice Christopher J. Heffernan was a calculated move. Heffernan was known as a jurist of independence and rigor—“aggressive and fearless,” in contemporary descriptions. By appointing a sitting judge rather than a political operative, Smith shifted the frame of the investigation from politics to jurisprudence.

The legal foundation for this action rested in the Governor’s authority under New York law, including the Moreland Act and provisions allowing for the removal of public officials for dereliction of duty. These statutes gave Smith broad investigative power, but their legitimacy depended on how they were used.

Heffernan’s role was not symbolic. He was tasked with gathering evidence, conducting hearings, and establishing a factual record. In effect, he functioned as a one-man commission—an extension of the Governor’s authority, but insulated by judicial credibility.

The structure mattered. Rather than issuing accusations, the state would build a case. Rather than relying on rumor or press accounts, it would rely on testimony and evidence. And rather than rendering a political judgment, it would produce findings that could justify formal action.

The investigation began with urgency.

V. The Inquiry: Evidence, Silence, and Exposure

As Heffernan began his work, one fact quickly became undeniable: the existence of open gambling in Saratoga was not in dispute.

Witnesses described operations that functioned in plain view. Gambling houses operated openly. Betting occurred with little concealment. The scale and visibility of these activities suggested not occasional enforcement failures, but systemic non-enforcement.

The question, therefore, was not whether illegal activity existed.

The question was why those responsible for enforcing the law had failed to act.

Three officials came under particular scrutiny:

District Attorney Andrus
Sheriff Wilmot
Commissioner of Public Safety Arthur J. Leonard

Each held a position that carried clear statutory responsibilities. Each had the authority—or at minimum the obligation—to intervene.

And yet, during the investigation, a striking pattern emerged.

They did not testify.

Heffernan noted this absence with pointed clarity. Despite the established evidence of gambling operations, not one of the officials offered a substantive defense or explanation. Their silence became, in effect, part of the evidentiary record.

This was not a procedural technicality. It was central to the inquiry’s conclusions. In legal contexts, silence can be interpreted in multiple ways. But in this instance—where public officials faced documented failures to enforce the law—it took on a particular significance. Heffernan framed it as an implicit admission: that the officials could not defend their actions without exposing further dereliction.

The investigation thus moved from exposure to judgment.

VI. The Heffernan Report: Findings and Consequences

On September 15, 1926, Heffernan released his report.

Its conclusions were direct and unequivocal.

The officials in question had failed to perform their duties. Illegal gambling had operated openly and persistently. The responsible authorities had not intervened in any meaningful way.

The report characterized this failure as more than negligence. It was dereliction of duty—“wilful and criminal” in its implications.

The recommendations were clear:

Removal of District Attorney Andrus
Removal of Sheriff Wilmot
Removal of Commissioner Leonard

Heffernan’s reasoning rested not only on the existence of illegal activity, but on the officials’ failure to respond to it. Their inaction, combined with their refusal to testify, created a compelling case for removal.

The report transformed the investigation from inquiry to action.

It now fell to Governor Smith to decide.

VII. The Governor’s Decision: Authority Asserted

Smith’s response was swift.

He made the findings public and issued an ultimatum: the officials had until September 20 to respond before he would take action.

This deadline was more than administrative. It was strategic.

By setting a fixed timeline, Smith signaled decisiveness. By making the process public, he reinforced transparency. And by grounding his actions in Heffernan’s findings, he anchored his decision in evidence rather than politics.

The framing was deliberate.

Smith was not acting against individuals. He was acting on behalf of the law.

The narrative that Finley had attempted to construct—that of a Governor protecting friends—collapsed under the weight of the process Smith had chosen. Instead, Smith emerged as an executive willing to confront local power structures when they conflicted with state law.

The balance of authority shifted.

VIII. Saratoga Reconsidered: Local Autonomy vs. State Power

The implications of the investigation extended beyond the individuals involved. At its core, the episode redefined the relationship between local governance and state authority in New York.

Saratoga had long operated under an informal understanding: that certain activities, while technically illegal, would be tolerated if they sustained the local economy. This arrangement depended on discretion, selective enforcement, and mutual accommodation between officials and operators.

The Heffernan investigation disrupted that equilibrium.

It established that:

Visibility matters: Open violations of the law invite intervention
Responsibility is enforceable: Officials can be removed for inaction
State authority is not symbolic: It can override local practices when necessary

The “Monte Carlo” model of Saratoga—its reputation as a place where rules were relaxed—could no longer operate without risk.

IX. The Broader Political Context

Smith’s actions also resonated beyond Saratoga.

In the 1920s, debates over law enforcement, morality, and governance were intensifying across the United States. Prohibition, in particular, had exposed tensions between federal law and local compliance. In many places, enforcement was inconsistent, selective, or openly resisted.

Saratoga’s situation mirrored those dynamics.

By intervening decisively, Smith positioned himself within a broader national conversation about the role of government in enforcing law. His actions suggested that tolerance had limits—and that those limits would be enforced when crossed.

For Smith personally, the episode strengthened his image as a capable executive. It demonstrated that he could navigate complex political terrain while maintaining legal integrity.

X. Conclusion: A Turning Point in Executive Governance

The 1926 Saratoga investigation stands as a defining moment in New York’s political history.

Governor Alfred E. Smith entered the episode under suspicion—accused of potential inaction and compromised by association. He emerged from it as a decisive enforcer of state authority.

By appointing Justice Heffernan, Smith transformed a political challenge into a legal process. By acting on the findings, he reaffirmed the principle that public office carries enforceable obligations.

The legacy of the investigation lies in its clarity.

It demonstrated that:

The rule of law cannot coexist indefinitely with visible, tolerated violations
Public officials are accountable not only for their actions, but for their failures to act
Executive authority, when exercised with discipline and transparency, can reset entrenched systems

Saratoga did not cease to be a place of leisure, wealth, and spectacle. But after 1926, it could no longer claim exemption from the authority of the state.

And in that shift—from tolerated disorder to enforced accountability—Governor Smith secured his place as the ultimate arbiter of law in the “Spa City.”