Podcast Summary: The Dollop with Dave Anthony and Gareth Reynolds

Episode: 687 - Larry Sullivan - Live
Release Date: June 10, 2025

Introduction

In this episode of The Dollop, comedians Dave Anthony and Gareth Reynolds delve into the intriguing and tumultuous life of Larry Sullivan, a notorious figure from American history. From humble beginnings in St. Louis to becoming a pivotal player in Portland’s underworld and beyond, Sullivan's story is a blend of ambition, criminal ingenuity, and eventual downfall.

Early Life and Boxing Career

Larry Sullivan's early life remains largely undocumented, primarily due to his impoverished background in St. Louis. At the age of 20, seeking a fresh start, Sullivan relocates to Oregon. Initially settling in the tough, working-class port town of Astoria, Sullivan channels his physical prowess into boxing.

Dave Anthony [02:04]: "Larry was very tough himself and he had no skills. So he decided to become a boxer."

Under the brutal London rules of the time—characterized by bare-knuckle fighting and no time limits—Sullivan quickly rises to prominence, becoming Astoria’s top prizefighter. His undefeated streak, though exaggerated in local lore, cements his reputation as a formidable force in the ring.

Gareth Reynolds [06:25]: "72 rounds, everyone's like, well, that's crazy."

Despite his success in Astoria, Sullivan faces challenges when he steps onto the bigger stage in Portland, where his fighting skills are put to the ultimate test, resulting in his eventual decline in the boxing world.

Transition to Shanghaiing and Crimping

Unable to sustain his boxing career in Portland, Sullivan turns to shanghaiing—the practice of kidnapping individuals to serve as sailors on ships under false pretenses. Leveraging his connections with the local sailor's boarding house owners, Sullivan masters the art of coercing unsuspecting bar patrons into forced labor.

Dave Anthony [12:31]: "Shanghaiing means kidnapping or coercing a random guy into forced labor on his ship."

Sullivan's strategic approach involves various deceptive methods, including drugging victims or using physical force, ensuring a steady supply of labor for maritime ventures. His boarding house becomes a hub for recruiting sailors, solidifying his status in Portland's underworld.

Sullivan's Political Influence

Recognizing the power of political manipulation, Sullivan utilizes his boarding house to influence local elections. By importing transient sailors who can vote multiple times without detection, he sways electoral outcomes to favor his interests. This savvy move integrates him into the political machinery of Portland, granting him protection and expansion opportunities.

Dave Anthony [28:01]: "Larry was the first crimp to figure out the true value of owning a sailor's boarding house."

Sullivan’s alliances extend to local law enforcement and other powerful crimps, creating a cartel-like structure that dominates Portland’s criminal landscape. His influence ensures minimal legal repercussions for his activities and establishes a robust network for his illicit operations.

Robbing the Robbers Scheme

Sullivan devises an ingenious scheme known as "robbing the robbers," where he manipulates ship captains into hiring new, more expensive crews. By orchestrating petty crimes among sailors, he ensures a constant flow of crew members who are entangled in legal troubles. When captains inevitably face crew shortages due to these distractions, Sullivan forces them to pay exorbitant fees for replacement sailors.

Dave Anthony [31:07]: "Instead, Larry and his gang forced the captains to hire a brand new crew at a higher cost."

This method not only maximizes Sullivan’s profits but also ensures that ship captains remain dependent on his services, further entrenching his control over Portland’s maritime industry.

Legal Challenges and Downfall in Portland

Sullivan's operations eventually draw legal scrutiny. A pivotal lawsuit, Robertson vs. Baldwin, challenges the legality of shanghaiing under the 13th Amendment's prohibition of slavery. Despite the apparent link, the Supreme Court rules in favor of the captains, as sailors are not exempt from the amendment's reach.

Dave Anthony [25:03]: "Nor should we. But at 20 years old, he ventured off."

This setback, coupled with increased public outcry and international condemnation—particularly from British and German consulates—forces Sullivan to reassess his position in Portland. The impending Lewis and Clark Centennial Exposition further complicates his efforts to maintain control, as an influx of tourists disrupts his established networks.

Move to Goldfield, Nevada and Partnership with George Graham Rice

Seeking new opportunities, Sullivan relocates to Goldfield, Nevada, a burgeoning boomtown characterized by lawlessness and rapid economic growth. There, he partners with George Graham Rice, a charismatic gambler and advertising genius, to launch the Sullivan Trust Company. Their venture focuses on mining stock fraud, leveraging Rice's expertise in crafting compelling human interest stories to entice investors.

Dave Anthony [51:06]: "They all featured George's clients as heroes."

Their collaboration epitomizes the speculative bubbles of the early 20th century, where misinformation and deception drive financial gains. By salting mines—planting valuable minerals to fake productivity—Sullivan and Rice mislead investors into believing in the profitability of their mining ventures.

The Sullivan Trust Company and Mining Fraud

The Sullivan Trust Company experiences rapid growth, fueled by deceptive advertising and speculative investments. Sullivan's political savvy and Rice's persuasive campaigns create a facade of legitimacy, allowing them to amass significant wealth. However, the lack of actual mining productivity means that their success is built on shaky foundations.

Dave Anthony [52:12]: "And split it into a million shares."

Their fraudulent activities go unchecked until financial discrepancies and growing skepticism lead to the company's collapse in 1907. The fallout includes international scandals, further damaging their reputations and contributing to the eventual demise of their schemes.

Final Years and Death

Following the collapse of his ventures, Sullivan's influence wanes. He attempts to diversify his criminal activities, including private detective work in Los Angeles, where he collaborates with renowned lawyer Clarence Darrow. However, legal troubles persist, and Sullivan becomes increasingly entangled with law enforcement allegations, such as the unproven bribery in the McNamara brothers' case.

By the onset of World War I, Sullivan secures a more mundane position as a security man at a shipyard, reflecting the decline of his once-dominant criminal empire. His life concludes in 1918 due to kidney disease, likely exacerbated by years of hard living and substance abuse.

Dave Anthony [66:23]: "Larry died in 1918 of kidney disease, probably from drinking."

Larry Sullivan's legacy is a testament to the complexities of American underworld history, illustrating how ambition and cunning can both build and destroy a man.

Conclusion

Larry Sullivan's story, as recounted in this episode of The Dollop, offers a fascinating glimpse into the darker aspects of American history. From his rise as a celebrated boxer to his role as a master manipulator in Portland and Nevada, Sullivan embodies the relentless pursuit of power and wealth. His eventual downfall serves as a cautionary tale about the limits of criminal ingenuity and the inevitable consequences of unchecked ambition.

Notable Quotes:

• Dave Anthony [06:33]: "So back then it's like eight."

• Gareth Reynolds [35:20]: "Yeah, he's got the piece of shit collector's kit."

• Gareth Reynolds [44:35]: "Wake up on a ship. Ah, well, I heard you liked exploring."

• Dave Anthony [58:44]: "No, what we love about podcasting is it's a space where you can talk."

Sources:

• Sullivan, Larry Boxer Connor Shanghai baller Riverboat party turned out to be the shanghaiing trick.
• Portland's seeding Seafaring past by Dale Bays and tunnels get to underbelly of Portland's Lava's pass by Joseph Fraser.
• My adventures with your money by George Graham Rice.
• The Evening Star and the Tillamook Headlight Herald.