Jessie Street: The Rocket’s Shadow

To the untrained eye, Jessie Street is nothing more than an alley—a spillover from San Francisco’s relentless churn of progress and decay. But for those who know where to look, it’s a place alive with ghosts, a site where the city’s ambitions have repeatedly faltered, unable to escape the absurdity of modernity, leaving behind a palimpsest of unfinished dreams and unresolved histories.

Into this frayed tableau steps Daniel Lurie, the city’s freshly minted mayor, flanked by a team of administrators plucked from corporate boardrooms and tech startups. The former executive of the San Francisco Giants, a man whose tenure oversaw a dynasty of championships and the economic revitalization of Mission Bay, is now tasked with a different kind of legacy. His role here, like the rest of Lurie’s team, is to find a way to reimagine San Francisco—to make its streets feel safe, its housing crisis less acute, and its residents less estranged from the glittering promise of the city they call home.

But Jessie Street isn’t Mission Bay, and it doesn’t bend to clean narratives or sharp marketing campaigns. Where the baseball park rose, displacing shipyards and industrial debris, Jessie Street resists. Its walls, patched with graffiti and tarps, seem to push back against renewal, holding fast to the weight of history: the rooming houses of the early 20th century, the waves of migrant workers who once called the South of Market home, the first whispers of the gay liberation movement that germinated here, and the long, slow descent into its current state—a corridor of violence, addiction, and mental illness.

On April 13, 2024, as Lurie’s team drafted its transition strategies in a boardroom overlooking the city, Jessie Street reminded everyone that its crises are not abstract. Five gunshots shattered the fragile quiet of the morning. A black Prius became collateral damage, its glass a sharp confetti on the ground. A man, clutching his side, ran toward the corner liquor store, leaving a thin trail of blood that marked his passage.

By the time the police arrived, the alley was a crime scene again, its daily rhythm interrupted by the flashing lights of patrol cars and the methodical gathering of evidence. Reports would later describe it as an “isolated incident,” but nothing about the alley feels isolated. Each act of violence here is part of a larger system, a cycle fed by addiction, desperation, and the city’s inability to address the root causes of its decay.

Months later, on September 13, gunfire echoed again, this time spilling beyond the alley. A man with a firearm fled from officers into the chaos of downtown, the chase ending in an officer-involved shooting near the Powell Street BART station. These moments, sharp and loud, seemed to punctuate a truth that everyone already knows but struggles to articulate: Jessie Street is a pressure valve for a city on the brink.

For Lurie and his administration, the alley is a crucible, a place where the tension between ambition and reality crystallizes. The former Giants executive, now tasked with untangling the mess of city politics, sees potential in data and efficiency, in applying the logic of wins and losses to governance. His team’s confidence is palpable, buoyed by their pedigrees and past successes, but the alley has little patience for theory.

To walk Jessie Street is to feel the weight of what cannot be solved by metrics alone. It is not just a site of urban failure but a living, breathing indictment of decades of policy choices. The systemic neglect of mental health care, the criminalization of poverty, the endless push toward development without regard for those left behind—all of it converges here.

The new administration may draft plans and hold press conferences, but the alley demands more than just policy; it demands reckoning. This is not a place where solutions can be rolled out in tidy timelines or where success can be measured in quarterly reports. It is a place that requires sustained attention, resources, and a willingness to face uncomfortable truths about what San Francisco has become.

There’s a rumor (or maybe a social media post) that Lurie and his team visited the alley early in their tenure, not as a public gesture but as part of their internal strategy sessions. They walked its length, past the tents and broken bottles, the faint scent of ammonia clinging to the air. They paused at the corner where the shootings had occurred, their presence a reminder of the city’s unspoken hope that new leadership might finally bring change.

In my last essay I made parallels to David Foster Wallace's book Infinite Jest. This morning as I read new articles in the paper about Lurie's administration I thought about another book Gravity's Rainbow, by Thomas Pynchon (I'm only making these parallells because both books are super long and I'm trying to seem smart; I'm not; this is all AI; I'll probably reference Joyce in the future). In Gravity’s Rainbow, Thomas Pynchon’s world is governed by entropy, where the illusion of control dissolves in the face of chaos. The characters move through war-torn landscapes marked by the impenetrable logic of the V-2 rocket—its path calculated, its impact inevitable, its meaning always just out of reach. Tyrone Slothrop, the novel’s wandering antihero, stumbles from one premonition to another, his journey as much about what he cannot see as what he cannot escape.

Enter Daniel Lurie, freshly elected mayor of San Francisco, stepping into the city’s fractured narrative as a character Pynchon might have written himself. He carries the weight of inherited ambition and carefully polished optimism, surrounded by a team that speaks the language of progress and innovation. But their first visit to Jessie Street (maybe because they heard about me), a shadowed alley barely noticed in the city’s sweeping plans, feels less like a step toward renewal and more like the beginning of a parable.

Jessie Street is no ordinary place. It holds the kind of gravity that Pynchon writes about—a weight of history and neglect, of lives lived at the margins of control. Lurie’s walk down its uneven pavement, past tents sagging against brick walls and shards of broken glass reflecting the weak sunlight, might as well be a journey into his own uncertainty.

Pynchon’s Slothrop doesn’t understand the forces shaping his life; the rocket looms in the distance, its trajectory unavoidable, its endpoint unknown. Lurie, too, might not yet grasp the full implications of his role. Jessie Street has seen the weight of the city’s failures, from housing policy to addiction to the criminalization of mental illness. It is not a site that can be easily controlled or transformed, but one that absorbs and resists. The tent cities that return days after sweeps, the violence that punctuates the silence with sudden gunfire—these are the alley’s entropy, its resistance to order.

When Lurie stood at the corner, flanked by aides and advisors, what did he see? Was it a site for renewal, a challenge to be met with the tools of governance and innovation? Or was it something else, something more ominous—a premonition of rupture, of a future that even his administration might not be able to contain?

In Gravity’s Rainbow, the rocket does not just destroy; it signifies. Its descent marks a point of no return, a moment where what has been suppressed or ignored becomes unavoidable. Jessie Street feels like such a place, not yet exploded but weighted with the inevitability of conflict. It is not hard to imagine this alley, already the site of so much chaos, becoming the focus of something larger, sharper, and more devastating.

Lurie’s administration, like Pynchon’s war-struck characters, is trying to navigate a system that defies clear boundaries. His team of corporate and tech executives speaks in the language of solutions, their plans precise and actionable. But Jessie Street is not a problem to be solved; it is a point of convergence where the city’s competing narratives of progress and failure collide.

The alley resists the logic of renewal. It absorbs plans and initiatives the way its cracked pavement absorbs rain, leaving behind a residue of good intentions and unmet expectations. Lurie’s visit may have been meant to mark the beginning of a new chapter for San Francisco, but like Slothrop wandering through Europe’s wreckage, he may find himself chasing a story whose ending is already written.

In Pynchon’s world, the rocket always falls. Whether Jessie Street becomes a symbol of renewal or a site of rupture may depend less on policy and more on the forces already set in motion. For now, the alley holds its ground, a heavy shadow stretching across the city’s ambitions. Lurie may hope to rewrite its narrative, but the weight of the rocket’s descent—and the city’s own entropy—remains.