Midtown East: East 44th Street between 5th and Madison

Tucked between the crowds of Fifth Avenue and the churn of Grand Central, this otherwise anonymous block has, for more than a century, quietly served as a crossroads of American prep.

Around the turn of the 20th century, alumni organizations for Ivy Leagues clustered in this area, setting the tone for what would eventually be called Club Row. The Cornell Club is on this block, while many of the others are one block west of Fifth Avenue. The rest of this stretch has been defined by clothiers, most notably Brooks Brothers and Bill Blass.

This block also falls within the East Midtown rezoning area, which means the character of the block is on borrowed time. Take a peek on Google Maps here.

5 East 44th Street | 2009

The clean lines and brightly accented columns of this modern 20-story apartment building feel a bit like Tokyo meets Ikea. It throws a splash of color on an otherwise buttoned-up block.

It had the poor timing of breaking ground as the 2008 financial crisis was starting, which led to stalled progress and financial issues. Still, it’s a desirable address today and if you’ve got $2.8 million this 1,400 square foot apartment can be yours.

Back in the 1890s, though, this was the home of Richard Albert Canfield, an art collector who was known as the “prince of gamblers.” With the help of Stanford White, Canfield remodeled his townhouse, including a centuries-old bronze door sourced from Venice and a collection of James Whistler paintings. (Here’s a view inside.)

Behind a secret wall panel, VIPs found illegal poker games and roulette tables. Though it was widely known for years that “thousands are lost and won there every night on the throw of a die or the turn of a card” it wasn’t until 1902 that police finally shut the place down. New Yorker later recounted the scene in 1927:

“There was a scurry as rich men, abandoning $125,000 on the tables, fled through a trick tunnel. All escaped, but for days there were rumors of subpoenas and scandals in high places. Canfield ended the suspense with a cablegram from Europe, where he was vacationing. “Let my customers alone,” he said. “I’m coming back to plead guilty.” He did and was fined $1,000. The bronze door never opened again.”

Ephemeral New York features a great painting two years before Canfield died after falling down a step at the Union Square subway station.

346 Madison Avenue, the Brooks Brothers flagship | 1915

Just as the conservative Norfolk jacket slipped into extinction, this 10-story temple of tweed¹ is not long for this world.

For decades, this was the Brooks Brothers flagship, a major destination for those looking to project a kind of conservative stability in navy suits and striped ties. As Daytonian in Manhattan notes, Ralph Lauren worked here as a store clerk in 1964, and the building’s address at 346 Madison Avenue even inspired the name of company’s tobacco line.

(It wasn’t all cuffs and collars — in the middle of the 20th century the building also housed offices for a dude ranch.)

Nevertheless, this was many of the retail spaces that didn’t survive the 2020 Covid pandemic and the shift to work from home. It closed in 2020 and is slated to be demolished and replaced by a 41-story office building called 44+Madison sometime in the coming months, according to NY YIMBY.

The Cornell Club | 1921

This dignified brick edifice was originally home to the Chicago Pneumatic Tool Corporation, which made heavy equipment for mining and construction. (They’re still around!) Cornell took over the building in 1989.

Inside is a hotel, ballroom, and dining rooms for students and alumni of Cornell and other colleges. For those living outside the New York area, annual dues cost from $146 for recent graduates to $628.

Sadly, a NYPD traffic enforcement agent was run over by a truck in front of the building in 2013.

14 East 44th Street | Late 1800s

This is kind of a weird one. It’s clearly very old but went through a strange adaptation some time ago. It started its life as a fashionable townhouse and was once the home of the guy who invented the sleeping car for trains.

By the dawn of Prohibition, the house had changed and in 1926, it was home to the Bridge Whist Club, one of many speakeasies that dotted Manhattan at the time. But what the patrons didn’t know was that the operation was a honey pot run by a federal Treasury Department official tasked with shutting down illicit boozeries. According to the Bowery Boys:

Rubbing elbows with drinkers, agents could theoretically get names of other speakeasies and establish connections to leaders in New York’s underworld. Tables were even equipped with recording devices to pick up incriminating details.

Unfortunately for the clientele, the authorities used wood alcohol, which—as we’ve discussed—isn’t that great for you. The sting was only moderately successful and was shut down within the year, eventually becoming a public scandal for the treasury official.

There’s a deli on the ground floor which, if you go by Google Streetview, has been closed for at least 5 years.

What’s Good: There’s some really interesting history here.

What’s Not: It’s sort feels sort of…inert?

Block Rating: 4/10