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The completion of the Panama Canal in 1914 inspired two wealthy men—Flagler on the East Coast and Spreckels on the West Coast—to build railroads to deep-sea ports on opposite sides of the continent.
Because of my interest in both of these railroads, I asked Grok (the new google) to write a comparison of their histories and impacts. As follows.
The tale of ambitious railroads connecting major shipping ports to the wider world often reads like epic adventures of vision, engineering triumph, and eventual fate. Two standout examples are the San Diego region's quest for direct eastern rail access via the San Diego and Arizona Railway (linking to Arizona/California desert lines), paired with the bustling Port of San Diego, versus the Florida East Coast Railway's legendary Overseas Railroad extension to Key West and its deep-water shipping port.
Imagine two dreamers in the early 20th century: one in sunny Southern California, the other in balmy Florida. Both sought to unlock their ports' potential by forging iron paths across impossible terrain—one through rugged mountains and desert gorges, the other across open ocean and fragile keys.
1906-1919: The Western Saga: San Diego's "Impossible Railroad" and the Port's Enduring Link
In the early 1900s, San Diego dreamed of becoming a major Pacific gateway, rivaling San Francisco or Los Angeles. Its natural harbor—the Port of San Diego—was excellent, but the city lacked a direct rail route east. Goods from the Midwest or East had to detour north via Los Angeles, costing time and money. Enter John D. Spreckels, a wealthy entrepreneur who, with quiet backing from railroad titan E.H. Harriman (of Southern Pacific fame), launched the San Diego and Arizona Railway in 1906.
Dubbed "The Impossible Railroad" by skeptical engineers, it carved 148 miles through treacherous territory: crossing into Mexico near Tijuana, climbing the Coast Range, and plunging through the dramatic Carrizo Gorge with its 17 tunnels, endless trestles, and brutal desert conditions. Construction cost a fortune—around $18 million (far over estimates)—and took over a decade amid floods, sabotage, and landslides. Finally, in 1919, the line opened, connecting San Diego directly to El Centro, where it met Southern Pacific's transcontinental routes (effectively tying into Arizona-area networks via Imperial Valley lines and Southern Pacific's Overland Route extensions).
The payoff? The Port of San Diego gained better access for freight—agricultural goods from the Imperial Valley, imports/exports, and military cargo (San Diego's naval importance grew). Though the original SD&A faced repeated washouts and was sold to Southern Pacific in 1932 (becoming the San Diego and Arizona Eastern), pieces survived. Today, freight rail persists through short lines like the San Diego and Imperial Valley Railroad, interchanging with BNSF Railway in downtown San Diego. The Port remains rail-served (on-dock options near BNSF yards), supporting billions in goods movement along the LOSSAN Corridor (the vital coastal line to the national network). The dream evolved but endured—San Diego's port thrives with modern rail ties to the continent.
1905 -1912: The Eastern Epic: Flagler's Folly and the Key West Port Dream
Far across the continent, Henry Flagler—Standard Oil co-founder turned Florida developer—had already built the Florida East Coast Railway down the east coast to Miami. But his boldest vision came in 1905: extend rails 156 miles (including 128 beyond the mainland) to Key West, America's southernmost point. Why? Key West's deep-water harbor promised to become a vital Atlantic/Panama Canal gateway for trade with Cuba, Latin America, and beyond—ships could coal there, goods could flow rail-to-sea seamlessly.
Construction was monumental: over open water, building viaducts (like the famous Seven Mile Bridge and Long Key Viaduct), filling causeways, and battling hurricanes, mosquitoes, and storms. Crews numbered thousands; materials came from afar. Flagler, in his 80s, rode the first train into Key West in 1912, declaring it the "Eighth Wonder of the World." For a time, it worked—passenger trains rolled, freight moved, and Key West's port briefly boomed with Caribbean connections.
But nature had the final say. In 1935, the catastrophic Labor Day Hurricane—a Category 5 monster—smashed the Overseas Railroad, destroying miles of track, viaducts, and a rescue train. Over 400 died (including many WWI veterans working on road projects). The financially strained FEC couldn't rebuild. The line was abandoned; remnants were repurposed for the Overseas Highway (US 1 today). Key West's port never became the grand hub Flagler envisioned—no rail connection remains. Modern Florida East Coast Railway stops at Miami, serving eastern ports like PortMiami and Port Everglades, but Key West relies solely on trucks, ships, and ferries.
The Comparison: Triumph of Endurance vs. Romantic Ruin
Both railroads were born of bold vision to elevate their ports: San Diego's to break isolation and feed its harbor from the east (via Arizona/California links), Key West's to make it a hemispheric trade pivot.
- Engineering Feats: San Diego's battled mountains, deserts, and international borders; Key West's conquered the sea itself with pioneering marine viaducts.
- Lifespan and Fate: San Diego's line, though battered and shortened, adapted—today's BNSF-connected freight rail keeps the Port viable. Key West's lasted only 23 years before total destruction, leaving the port rail-less.
- Legacy: San Diego's story is one of persistence—the port remains a key player with rail access for military, commercial, and cross-border trade. Key West's is poetic tragedy—a magnificent "railroad that went to sea," now echoed in the highway bridges where trains once ran.
In the end, the San Diego-Arizona route and Port story endures as a gritty success of adaptation, while Flagler's Key West extension lives on as a legendary "what if"—a dream washed away by the very ocean it sought to tame. Both remind us: railroads can conquer nature for a time, but nature often has the last word.
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