Who was Major Deegan? Whose name is attached to NYC’s notorious jail? New book explores the city’s famous names

If you’ve driven on The Deegan, you’ve cursed it.

But who was Major Deegan or Van Wyck?

Rebecca Bratspies asks these questions in “Naming Gotham.” “When did they live? What did they do?... Everybody takes the Major Deegan, but nobody knows who he was.”

So, she decided to dig into the lives behind the names of roads, bridges, and institutions to see who these people were that they honor. As her book’s subtitle makes clear – “The Villains, Rogues & Heroes Behind New York’s Place Names” – they are a pretty mixed bag.

You would have expected Major William Francis Deegan to at least be more inspiring – even if only of fury. Deegan served during World War I supervising the construction of Army bases in New York. After, he helped form the American Legion, enforce health standards for New York City apartments, and run the Mayor’s Committee for Welcoming Distinguished Guests.

A loyal public servant, definitely. But worthy of his own expressway?

Still, he’s far more laudable than Robert Anderson Van Wyck, who posthumously gave his name to another busy road. It’s probably the only thing Van Wyck ever gave away for free. The first mayor of the consolidated, five-borough New York City, he perpetually had his hand out for a payoff.

When he was elected, the city’s scoundrels even celebrated. “Drunken gamblers and petty criminals marched through the Tenderloin district chanting, ‘Well, well, well, Reform has gone to Hell,’” Bratspies writes. A newspaper called Van Wyck and his corrupt cronies pure “ooze and slime.”

One backroom deal gave the American Ice Company a monopoly over a then-essential commodity and doubled the price. In gratitude, the company gave the mayor 5,000 shares of stock, roughly $12 million adjusted to today’s prices. A similar mayoral deal presented the Ramapo Water Company with a 40-year contract to supply the city’s needs; never mind that it was twice the going rate.

Van Wyck’s corruption was so outrageous that the state legislature stepped in and revoked the contract.

Eventually, Van Wyck amassed a fortune of more than $5 million. Considering his annual salary was $15,000, his corruption was impressive. Van Wyck retired comfortably to Paris. When he died in 1914, his obituary in the Times noted he had presided over “more administrative scandals than any Mayor in the City’s history.”

That didn’t prevent metropolitan master builder Robert Moses from later dedicating an expressway to him, even if he did get the name wrong (the mayor had pronounced it “Van Wike.”) Queried on the mistake, the autocrat reportedly snapped, “I’m Robert Moses. I can call it whatever I damn please.”

Other New York placenames have grimmer associations. Scottish immigrant Robert Lenox arrived in America shortly before the Revolution, building a thriving mercantile business tied to the slave trade. When one of his enslaved people escaped, Lenox promptly placed an ad offering a reward for the return of his “property.”

His name lives on hospitals, libraries, neighborhoods, and Harlem’s main thoroughfare. The avenue, renamed Malcolm X Boulevard, carries both names.

Slavery and exploitation also enriched the Macomb family, which gave their name to Macomb’s Dam Bridge and Park. After leaving Ireland for New York in the 1750s, Alexander Macomb first profited by illegally selling liquor to Native Americans. During the Revolutionary War, he traded with the British enemy.

Yet after the war, the mercenary Macomb moved into a Manhattan mansion and was “readily accepted into New York City’s nouveau riche society,” Bratspies writes.

Macomb’s greed was his undoing. A shady land deal in the Adirondacks led to an investigation by the New York State legislature. A subsequent attempt to corner the U.S. debt market helped cause the financial Panic of 1792. Ruined, Macomb was tossed into debtors’ prison and saw most of his holdings sold at auction.

Worst of all, perhaps, was the Riker family, who gave their name to an island and the notorious jail. During the War of 1812, Captain Andrew Riker sailed the seas as a privateer – essentially a licensed pirate, authorized to plunder ships sailing under the enemy’s flag. During the conflict, Riker captured more than 20 vessels and seized millions in cargo.

Still, he operated under the law, which is more than could be said of his even less scrupulous brother, Richard.

Publicly, he held various posts in New York City’s justice system for more than 30 years. Privately, he also reportedly operated as a member of “the Kidnapping Club.” Working with corrupt cops and officials, Riker used his government position as a recorder, Bratspies writes, “to declare Black people ‘runaway slaves’ without allowing them the opportunity to prove that they were actually free.”

They left New York in chains, sent to Southern plantations.

“Since his signature as recorder was required on manumission certificates issued within the city, Riker clearly knew the falsity of many claims he upheld,” she writes.

Black abolitionists called Riker “the spider at the center of a web of injustice.” His white contemporaries hailed him as “a near saintly man.” Never charged with any crime, he died in 1842 and is buried in Astoria.

After men like this, it’s a relief to find some actual heroes behind the place names.

Anne Hutchinson, a pioneering Colonial-era crusader for women’s rights and religious freedom, was forced to flee Massachusetts and then Rhode Island. She briefly found a haven in Pelham Bay – until 1643, when she died in a Native American attack. “Proud Jezebel has at last been cast down,” gloated Massachusetts governor John Winthrop. The Hutchinson River Parkway is her tribute.

Polish warriors Tadeusz Kościuszko and Casimir Pulaski are also honored.

A trained architect and military expert, Kościuszko left Europe to join America’s fight for independence. He helped fortify West Point and fought at the Battle of Saratoga before returning home. A fierce opponent of slavery, he asked that, after his death, his fortune be used to buy the freedom of enslaved Blacks and pay for their education. The stipulations were never carried out.

Another Polish patriot, Pulaski left in 1777 to come to America “where freedom is being defended, to live or die for it,” he declared. A master horseman, he organized the Continental Army’s cavalry, reportedly saved George Washington’s life during the Battle of Brandywine, and fought on battlefields from New Jersey to South Carolina. He died during the Siege of Savannah.

Be sure to spare these heroes a thought the next time you’re kvetching about your commute over the Kościuszko Bridge or Pulaski Skyway.

Of course, not everyone distinguished themselves on the battlefield. Were he a more selfish man, rags-to-riches Peter Cooper would today be known only for designing America’s first domestic-built locomotive, the Tom Thumb. But Cooper, who would go on to be one of the founders of AT&T, was determined to give back.

Although he had all of one year of formal school, he founded Cooper Union for the Advancement of Science and Art, which offered admission regardless of race, religion, or gender. It only began charging tuition in 2014. He was also a stalwart abolitionist and defender of Native American rights. After his death, the Cooper Institute helped found the NAACP.

Cooper stands as further proof that sometimes behind New York’s great place names was a great person.