World championships. Scientific breakthroughs. Pillars of higher education. Titans of culture, music, literature, and the arts. (Oh, and that whoopie-pie cupcake at Lulu’s.) Boston, as we are well aware, is no slouch in the triumph department.

Just ask any Bostonian, and we’ll tell you that even when we fail, we fail better. (And we won’t even apologize to Samuel Beckett for the shoddy paraphrase.) Parallel to Boston’s proud legacy lies another, less inspiring track — one prone to derailments, blunders, and fiascoes.


Look, nobody wants to dwell on our failures — which is why we’re just gonna move through them real quick. Some of these are major catastrophes, others are minor flubs — but all of them have in common a healthy helping of human error, failed judgment, or plain bad luck. In looking back on some of our worst moments (for this is no comprehensive survey of our city’s many travails), perhaps we can better predict or prevent those disasters that await us in the future — like when a rising waterfront becomes the aquarium’s de facto seal pond, or when the MBTA’s pilot hover-bus program somehow ends up in the harbor.

(Oh, and I’d be failing the manners my mother taught me not to thank local historians and Boston experts Bill Fowler, James Healy, Bob Allison, Gail Mazur, and Merry White for their help in keeping this list off this list.)

1630: ROADS TO RUIN

Blame the Puritans, more accustomed to shires than cities, who couldn’t see past the brims of their silly hats. Blame the cow snouts that lore tells us blazed the tangle of trails that became the streets that overtax our map apps. Blame the deleted deltas, the redrawn shorelines, and the fickle contours of the cityscape. Or better yet, blame Mother Nature for bestowing Boston with such inhospitable hills, marshes, forests, and other features that make a sensible grid impossible. All of these factors (except the cows) conspired to make Boston’s roadways look like my earbuds when they come out of my pocket. This organic seat-of-the-pantaloon approach to city planning set the stage for centuries of tension, anger, and inconvenience.


1670: BURIED HATCHETS

When the Saugus Iron Works first fired up in 1646, it was the New World place to get your nails done. (Also, pots, axes, saws, hoes.) Auspiciously situated along the Saugus River, which drove the wheel that pumped its mighty bellows, and on a site rich in bog iron ore and wood to make charcoal, the Works was a great success — eating up an acre of trees and churning out a ton of cast iron every day. But a scourge of corruption (i.e., double ledgers, suspected embezzlement) plus the high cost of skilled labor (specifically, indentured Scottish POWs who “sometimes doe frolicke to such purpose that they get before the magistrates”) drove the place into the ground in 1670 — where it would stay until 1948, when it was dug up by archeologists. I’ve got ten bucks that says it comes back as a CrossFit gym.

1692: HANG TWENTY

andrew Joyner for the Boston Globe

Looking back, the Salem witch trials were probably not such a great idea. Turns out, using “spectral evidence” to codify sincerely held heebie-jeebies toward the Puritan equivalent of the cool kids is not a sustainable approach to justice. The hysteria landed something like 150 accused witches in jail by May 1693 and ended with 20 either hanged or crushed by stones. It’s also indirectly responsible for decades of junior high thespians murdering Arthur Miller, over and over again.


1839: SINKING FEELING

In December 1839, a trio of snowstorms bashed the coast of Massachusetts, taking out dozens of boats and killing upward of 200 sailors. One of the most devastating of these wrecks was the schooner Catherine Nichols, which makes our list for a momentary, yet catastrophic, lapse in judgment. As Southworth Allen Howland tells it in his 1840 account, the schooner’s captain believed it “sheltered by the high hills from the violence of the tempest” anchored on the southwest side of Nahant — close enough to shore that the crew could have easily reached it. Instead, they all remained aboard. Within 30 minutes, the winds shifted and the boat broke adrift, smashing into the “shelving rocky shore, where she immediately went to pieces.” Three men perished, including the first mate, who was later found “destitute of every particle of clothing, except his stock and stockings.” So the next time you want to be a hero and drive to Cumby’s in your robe during a blizzard: This.

1861: CRASH COURSE

On July 4, 1861 — less than a year after one of the most recognizable aerial photographs of Boston was taken from its car — the hot-air balloon Queen of the Air made an ill-advised ascent over Boston. According to The New York Times account of what would be dubbed a “Perilous Balloon Adventure,” “the wind being seaward, the air-ships were carried out in that direction” and “it was wafted over East Boston, and seaward toward Nahant.” Attempts to find a steady altitude failed, and rather than stray farther over the open ocean, the two passengers — balloonist Seth Simmons and Herald reporter E.B. Haskell — opted “to come down and trust to Providence for safety.” The craft crashed into the water, throwing the two from the balloon, then dragging them for several miles as they “held on to it with most tenacious grasp.” They were eventually scooped up by the crew of the schooner Atlantic. As lucky as they were to have lived, they were even luckier the Times didn’t have an online comments section yet.


andrew Joyner for the Boston Globe

1878: BLAND IN BOSTON

Nobody likes a party pooper, and the Watch and Ward Society, founded in 1878, was put on this earth to party poop. The frothy crest of a wave of self-appointed moral watchdogs, the WWS spent 80 years obsessing over Boston’s naughty bits: surveilling gay bars, banning (not very) racy books and plays, busting poker games and Turkish baths, and, in time, keeping fed the burning-ire furnace of Boston Licensing Board chair and Queen of Killjoy Mary Driscoll, whose buzzkill cross hairs targeted everyone from rock ’n’ rollers to drag queens through the 1950s. The embarrassing effectiveness of the WWS left Boston saddled with a stubborn legacy of provincial no-funism that dogs our good times to this day.


1896: HIS OWN DEVICES

Roxbury inventor/badass Sylvester Roper dazzled the scientific community in 1863 with the construction of his steam-powered carriage, which could reach 20 m.p.h. on 60 pounds of steam pressure. By 1867, he had moved on to building his own velocipedes — steam-powered bikes flanked by boiler tanks — that, according to one ad, could “out speed any horse in the world.” By 1896, it was said that Roper’s bikes could reach up to 40 m.p.h., but to make that official (i.e., show off), he gave a public exhibition at the Charles River racetrack. After a few successful high-speed laps, Roper wobbled, lost control, and was killed when he was thrown off the track. In a twist, the cause of death was later determined to be a heart attack. So I guess the lesson here is to maybe cut down on fried foods.

1897: WICKED LEAK

On March 4, 1897, after weeks of complaints over leaking gas wafted past gas company officials like so much leaking gas, an accumulation of (you guessed it) leaking gas set off a massive gas explosion at the corner of Boylston and Tremont streets. According to an account in a 1903 edition of New England Magazine, streetcars were instantly incinerated, shop windows shattered up and down the block, “a dentist in the Hotel Pelham . . . was blown away from the patient on whom he was operating,” 60 people suffered injuries, and six died. So just in case that howling, squealing turn that the Green Line makes at Boylston doesn’t set your hair on end already, maybe this will help.

1919: DEEP TROUBLE

andrew Joyner for the Boston Globe

All Bostonians know that first hot summer day when they pretend to smell molasses rising off the hot pavement from this, the most storied disaster in our history. The construction of a 2.3 million-gallon tank to hold molasses was overseen by one Arthur Jell, who allegedly opted to address visible leaks by painting the whole thing brown. (Investigations done decades later would reveal massive structural deficiencies that made the tank fundamentally unfit for the goo.) When it ruptured in January 1919, the tank unleashed a 25-foot wave of molasses that flooded two city blocks (up to the waist in some places), injured more than 150, and killed 21. The company, meanwhile, swiftly blamed the disaster on Italian anarchists — so there’s a bonus spoonful of good old-fashioned racism to sweeten the fail pot.

andrew Joyner for the Boston Globe

1919-2004: HOMETOWN ZEROS

A few months after Babe Ruth’s last game in September 1919 (the Sox had won the 1918 World Series), the news broke in the Globe: We were giving him to the Yankees. “What the Boston fans want, I take it, and what I want because they want it, is a winning team,” clarified owner Harry Frazee, as fate turned the echo knob all the way to the right, “rather than a one-man team which finishes in sixth place (place . . . place . . . place . . . ).” I don’t really have the print real estate or emotional fortitude to fully explain what occurred over the subsequent decades. Do any of us? I’m only revisiting this because I have to, so let’s get it over with: The Man Who Held the Ball; the 1948 tiebreaker; the Yankee World Series buffet from ’49-’53; the Cardinals (again) in ’67; The Big Red Machine; Bucky (expletive) Dent; Bill (expletive) Buckner; the Grady/Pedro thing in 2003; and while we’re at it, yes, pink hats.

andrew Joyner for the Boston Globe

1920: GOT BILK?

While Bernie Madoff is considered by many to be the king of the Ponzi scheme, the namesake of these swindles got his start shaking down Bostonians back in 1920. Having relocated to Boston (after a couple stints in prison), Charles Ponzi cooked up a scheme that involved purchasing international postal reply coupons (don’t ask) overseas and then turning them for a profit in the States, promising his clients a return of 50 percent of their investment in 45 days. The influx of excited new clients allowed him to pay existing investors while skimming millions off the top — an unsustainable model that quickly collapsed to the tune of six ruined banks and $20 million in losses.

1967: STICKING IT TO THE MAN

Nearly 50 years after it was snapped, that famous photo of Boston Marathon official Jock Semple lunging after number 261 — Syracuse University junior Kathrine Switzer — and tearing at her race numbers still makes steam come out of our collective ears. For 70 years the Marathon had forbidden women from taking part. Switzer entered using her initials, wore lipstick, and dared anyone to get in her way. Switzer recalls hearing Semple’s loafers scraping the pavement behind her as he grabbed and growled: “Get the hell out of my race and give me those numbers!” His not-so-noble effort failed . . . one, because of history, and two, because her boyfriend body-checked Semple out of the way. Men: somehow missing the point of everything since forever.

andrew Joyner for the Boston Globe

1968: HALL OF SHAME

It’s hard to defend Boston City Hall, sitting there in its blah plaza, cracking internally like a dead molar waiting to be pulled. Cold and dark, imposing and uninspiring, technically and emotionally brutal, and apparently buckling under the weight of its own inadequacy, Gerhard Kallmann’s bore de force has been called “maybe one of the least-loved buildings in the known world” by the Globe and “a structure of dignity, humanism, and power” by the Times. This is likely because no one at the Times has ever had to renew a parking permit there.

1972: DEADLY PANELS

The construction of the former John Hancock Tower was beset with engineering errors and unanticipated problems from the get-go. First, the steel retaining walls warped during excavation, causing $11 million in damage to nearby Trinity Church. Later, the building was found to twist and sway in high winds, requiring millions to stabilize it. But perhaps the most memorable of the building’s flaws was its first set of windows, which were given to popping out — one 500-pound panel at a time — and crashing to the street below. All 10,344 panels had to be replaced at a cost of more than $5 million, often with temporary sheets of plywood. This moved the Harvard Crimson to warn shoppers to brace themselves for the “aesthetic shock” of “the unfinished checkered Hancock monolith.” Oh, and also the massive shards of death-glass falling from the sky.

1984: DOWN THE HATCH

andrew Joyner for the Boston Globe

Longtime Bostonians know well the micro-injustice of visiting another city, only to squint incredulously at your bar tab: Did they add wrong? No, silly. That’s just Happy Hour — a common tradition across the rest of America for people who enjoy things like happiness, good times, and cheap drinks, etc. In Boston, it was poured down the drain in 1984 by Governor Michael Dukakis. Advocates for the ban point to declining drunken-driving deaths since its implementation — but there’s no convincing correlation between the drop and the ban. Meanwhile, other vocal proponents have a financial stake in keeping your margaritas full price. And while loaded fries might be safer than loaded patrons, Happy Hour just represents yet another nice thing Massachusetts can’t have.

1988: BALLOT BALKS

Over the past 64 years, Massachusetts has been something of a mill of presidential candidates, rolling out more hopefuls for the highest office than any other state. But since 1988, that hope has rarely paid off; our streak hasn’t been such a winning one. Michael Dukakis couldn’t make it happen against George H.W. Bush back in ’88 (Happy Hour avenged?); John Kerry came up short against another Bush in ’04; and Mitt Romney (who technically hails from a very affluent section of outer space) got decisively Obama’d in ’12. If Elizabeth Warren is really considering a run sometime down the line, I suggest she start spending some quality time with lovable local icon Keytar Bear and lock up that ticket nice and early.

andrew Joyner for the Boston Globe

1990: OFF THE WALLS

On March 18, 1990, Richard Abath, a security guard on duty at the Isabella Stewart Gardner Museum, granted entry to two men dressed as cops and claiming to be investigating a disturbance. Abath and another guard were duly tied up with duct tape and moved to the basement, and the thieves proceeded to snatch works by Degas, Manet, Rembrandt, and Vermeer, whose masterpiece The Concert was valued at $200 million. Thirteen pieces in all were stolen, and 26 years later, a $5 million reward still awaits whoever secures their return. In the meantime, as history and Hollywood has repeatedly tried to teach us, if the cops at your door look suspicious (or anything like Ben Affleck or Jeremy Renner), maybe double-check before buzzing them in.

2006: ROAD WORRIERS

Just as the Big Dig, the most expensive and extensive highway project in American history (meant to solve some of the problems outlined in our first item), was finally, finally nearing completion — despite reports of “thousands” of leaks and concerns raised over the use of substandard materials — tragedy struck in the tunnel on July 10, 2006. Inadequately secured concrete panels weighing a combined 26 tons fell from the ceiling onto a car, injuring driver Angel Del Valle and killing his wife, Milena Del Valle. Technically it was a failure of a specific type of epoxy, but like many of the Big Dig’s failures, it was also a team effort.

2007: HIGH ANXIETY

andrew Joyner for the Boston Globe

When a marketing firm hired local artists Peter “Zebbler” Berdovsky and Sean Stevens to assist in a guerrilla marketing campaign to promote the Aqua Teen Hunger Force movie, they likely didn’t anticipate throwing the city into what would become known as the “Great Mooninite Panic.” On January 31, 2007, police received reports of a strange object stuck to the underside of the highway near Sullivan Square. Soon, more of these “suspicious devices” (which were nothing more than homemade Lite-Brites depicting the cartoon’s alien “Mooninite” characters flipping us all the bird) started being spotted downtown, under the Longfellow and BU bridges, and other conspicuous spots. Bomb squads and emergency vehicles were dispatched all over the city, roads and bridges were closed, traffic came to a halt, and Berdovsky and Stevens were arrested. Meanwhile, the rest of the country just gave us a concerned look and suggested we calm the hell down. The Boston Phoenix called it “the stupidest thing that has ever happened in Boston,” to which Boston replied, “Care to make it interesting?”

2015: THE AGONY OF DEFEAT

andrew Joyner for the Boston Globe

It’s hard to identify a single thing that went right with Boston’s failed 2015 bid to host the 2024 Olympic Games. The public hated the idea from the start, the organizers seemed to be going for their own gold medal in Shady Conduct (city employees, for example, were banned from expressing criticism of the bid), and you could practically hear the Green Line whimpering at the thought. Mayor Marty Walsh finally pulled the plug on the idea in late July, ending a yearlong embarrassment for everyone involved and inspiring a deep sigh of relief from a city learning its limits. After centuries of training, failing to reach what could have been our grandest failure yet sure feels like a win.

Michael Andor Brodeur can be reached at mbrodeur@globe.com. Follow him on Twitter @mbrodeur. Research assistance from Marisa Dellatto.