For decades, Santa Clara has been a city divided between its sunny façade of safe neighborhoods and civic pride, and a darker, entrenched world of political manipulation dominated by one family: the Gillmor’s. Readers have long asked for the full story behind my earlier exposé, and the time has come to connect the dots. What follows is not rumor or resentment but a documented pattern of power, influence, and retaliation that has shaped Santa Clara politics for more than forty years.
The Gillmor playbook is remarkably consistent: recycle old tactics, rename them, and use them to vilify anyone who resists their control. The so-called “49er 5” controversy—used to attack councilmembers Jain, Park, Hardy, Chahal, and Becker—was simply a modernized rerun of the “Stadium Five,” a slogan from a decade ago in which Lisa Gillmor was part of that “Stadium Five”. The script hasn’t changed. A small circle of loyalists stirs conflict, drags others into the drama, and keeps political fires burning for years, ensuring no reformer ever feels safe challenging the family’s dominance.
The roots of this dynasty go back to the late 1990s, when three sitting councilmembers—Dominic Caserta, Kevin Moore, and Jamie Matthews—worked for Gillmor & Associates. Even though Lisa Gillmor’s first time on council ended in 2000, her influence persisted through these loyal proxies till she returned back to the council in 2011. Decades later, her network reached as far as Oregon, funding campaigns like those of Jamie McLeod once a former advisary. Money has always been the Gillmors’ most potent weapon. In 2004, they distributed cash contributions to council candidates—far exceeding the legal $99 limit. When caught, they claimed ignorance and blamed the city clerk, an implausible defense for political veterans. Though Councilmember Karen Hardy filed suit, the issue quietly disappeared once cash was replaced with checks. No accountability, no consequences. Just like today, same story in a different year. Gary Gillmor once called campaign money the “lifeblood” of politics, dismissing donations as “peanuts”—the same language used to downplay financial risks in Measure J and the 49ers stadium deal. Such remarks reveal not naiveté, but mastery of the system.
The Gillmors’ empire was built as much on real estate as on rhetoric. From the late 1970s onward, Gary Gillmor brokered millions in public land sales including surplus from school property. His close ties to developers and city leaders allowed him to profit from deals involving the Santa Clara Unified and Alum Rock districts. In later decades, The Gillmor’s reaped benefits from city projects like the Mercado that financially benefited the Gillmor’s and then Franklin Square, where taxpayer-funded improvements boosted Gillmor-owned properties. The pattern of self-enrichment cloaked in civic language repeated in the Morse Mansion affair, when the city—under Mayor Lisa Gillmor’s leadership in 2016—purchased the historic property after years of neglect by the family itself. Conflict of interest concerns were brushed aside, as usual.
By the 2000s, the Gillmor network had extended its influence into neighboring cities. Campaign funds flowed into Gilroy, where pro-development candidates mysteriously received thousands in cash from undisclosed sources. Countywide, the Gillmor name became synonymous with big money politics, where alliances could be bought and loyalty was expected. Even a 1987 civil grand jury, investigating Santa Clara’s ethics policies and conflicts of interest, proved the troubling influence of then Parks and Rec Chair Lisa Gillmor and Planning Commission Chair Emmy Moore-Minister both were among those interviewed, foreshadowing the political tool that would follow.
From stadium schemes to convention center scandals, the family’s fingerprints are everywhere. In the 1990s, they championed Measure N for a San Francisco Giants stadium and later pushed for the Oakland A’s before embracing the 49ers project. Throughout, Lisa Gillmor’s message remained constant: defend financial interests under the guise of fiscal responsibility. When critics or competitors emerged, she turned to familiar tactics—audits, accusations of stonewalling, and media leaks—to shift the narrative. During the early 1990s, Gillmor and Mayor Eddie Souza accused the Chamber of Commerce of embezzlement at the Convention Center. After six-hour council interrogations produced no evidence and a non-Gillmor aligned Civil Grand Jury in 1994 agreed. City Manager Jennifer Sparacino warned that rumor-driven politics were “damaging the city.” The warning went unheeded, and similar tactics continue today.
Fast forward to the present, and the machinery remains intact. Under Mayor Lisa Gillmor’s leadership, leaks about Super Bowl costs, 49ers negotiations, grand jury reports and FIFA discussions have been weaponized to damage political rivals. Councilmembers Suds Jain, Kevin Park and Raj Chahal have publicly called out these breaches, while Gillmor herself has harassed officials such as former School Board President Vicki Fairchild for daring to question her when Gillmor pressured her for closed session information. This is not governance—it is vendetta politics. Those who stand up to her—find themselves isolated, attacked, or politically erased. Loyalty is transactional; dissent is unforgivable.
The parallels across decades are eerie. In 1993, Lisa Gillmor accused the Chamber of hiding documents and demanded performance audits of the Convention Center. In 2023, she made the same accusations—word for word—about the 49ers’ financial disclosures. In my previous letter to the editor I mentioned these same quotes, “I am not getting the documents.” “We are losing money.” “I want an audit.” “This issue is not going away.” Thirty years apart, the script remains unchanged. What might appear as passion for fiscal oversight is, in truth, a method of control—a political cudgel disguised as accountability.
Behind these tactics lies a deeper truth: the Gillmor machine thrives on division. By constantly reigniting old conflicts, it ensures that reformers never consolidate power long enough to enact systemic change. When political allies outlive their usefulness, they are discarded. When opponents emerge, they are smeared. This is not democracy—it is dynastic politics. The Gillmor’s have effectively privatized Santa Clara’s public narrative, transforming city hall into a stage for personal power plays.
The current council faces a choice: continue managing the chaos inherited from this dynasty, or confront it head-on. A united front of independent Councilmembers could finally end decades of manipulation. But if the upcoming elections restore the Gillmor faction—through a mayoral bid by Kathy Watanabe or any of Lisa’s loyalists—Santa Clara risks sliding backward into another cycle of secrecy and retaliation. The stakes are not just political; they are civic and moral.
The evidence across four decades is overwhelming. Campaign cash violations, land deals, phantom audits, influences over grand juries in 1987, 1991, 2016, 2022, 2024 and intimidation of critics form a pattern too consistent to dismiss as coincidence. From Gary’s real estate maneuvers to Lisa’s long campaign of control, the Gillmor family has turned Santa Clara into its private fiefdom. It is a legacy of power preserved through fear, not service.
The time has come for voters, watchdogs, and civic leaders to confront this reality. Santa Clara deserves transparency, ethics, and leadership unshackled from a single family’s ambitions. The Gillmor empire has thrived because residents looked away, believing stability was worth the price of silence. But silence is complicity. The unmasking of the Gillmor machine will not be complete until the city reclaims its politics from those who have treated public office as private inheritance. Only then can Santa Clara finally close this chapter of control and open one of accountability and renewal.