A half-pint called Squatter

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This little half-pint is Edward “Squatter” Benjamin, a NOLA native who in the 1920s and 30s-ish was a multi-sport sandlot and semipro stalwart. I tripped across this while doing freelance research for a project being undertaken by another writer — more on that later — and found it in the June 19, 1937, issue of the Louisiana Weekly.

I’d never heard of Squatter Benjamin before, but this picture was too, well, adorable to pass up. The context for the photo is the 1937 local sandlot season and a four-team city league created by Peter Robertson, a somewhat legendary figure on the Crescent City Negro Leagues scene about whom I’ve researched little up until this point.

There’s just so much rich, entrancing blackball history here in the Big Easy that I’ve never gotten around to digging much into the Pete Robertson legend. But what I do know is that Robertson managed and/or owned several baseball franchises over a few decades in the first half of the 20th century, and at least once he was involved in swirling controversies and power-struggle dramas.

But in early ’37, Robertson brought together area sandlot squads, including the Squatter Benjamin-managed Gypsy Tigers, in a citywide semipro league. At some point during the season — and I haven’t had time to glean too many details about this — the Gypsy Tigers were involved in a game that featured a controversial call that, according to some, tipped the contest against the Tigers and in favor of their opponents, the New Orleans White Sox, who won the game.

Squatter Benjamin, the skipper of the Tigers, then lodged a protest with league headquarters, such as they were, over the disputed incident. But, according to the caption from this Louisiana Weekly photo:

“Edward ‘Squatter’ Benjamin … withdrew his protest, for the benefit of the Peter Robertson City League, over a disputed play in a game last Saturday.”

As you can see with the header about the picture — “Sportsmanship” — Benjamin’s gracious move to drop his beef was well received by the local black press, which all season did its best to pump up and support the city league.

Benjamin’s decision to forgo his dispute for the good of the league was even reported in the mainstream white NOLA media at the time, including the Times-Picayune, which reported that Benjamin decided to drop his protest during a tete-a-tete between himself, Robertson and White Sox officials.

In the grand scheme of the long, complex history of the Negro Leagues in New Orleans — not to mention in the larger, gigantic, national blackball firmament — this incident is no more than a minor, barely perceived blip. But because of his tiny, sawed-off stature and goofy but absolutely appropriate nickname, Squatter Benjamin — like Black Diamond Pipkin, Iron Claw Populus and so many other fascinating NOLA Negro Leagues personalities — is worth a small historical glance …

Edward Benjamin was born, according to military records, on April 25, 1905. He was the fourth child, and third son, of Edward Sr. and Jennie — also called Lulu — Benjamin, who appear to both have been born in Alabama. Both Edward Sr. and Lulu were born during the Civil War years, which means they both could have been slaves originally.

However, Edward Sr.’s ancestral roots might be traced to Central America, possibly Costa Rica, and at one point — namely, the 1900 Census — Edward, Lulu and their burgeoning family were living in Vicksburg, Miss.


But the 1910 federal Census lists the entire family as “mulatto” living in an otherwise all-white neighborhood in NOLA. Edward Sr. was an odd jobs laborer in New Orleans; the family lived, at various points, on Gentilly Terrace Road and Allen Street. However, apparently at some point Edward Sr. became a minister but died between 1920 and 1930.

Edward Jr. went to to attend Straight College here in New Orleans — Straight was one of the progenitors or modern-day Dillard University — and became a teacher. The 1930 Census lists the 24-year-old Squatter living with his widowed mother and his brother, Roland, in New Orleans.

It was in the 1920s that Edward Benjamin Jr. became involved in the local semipro and sandlot sports scene; the little guy was a starting quarterback at Straight during his college years and for the semipro New Orleans Elks in the 1930s. On the diamond, Squatter pitched for the 1926 Caulfield Ads squad that won the Negro Southern League crown. Benjamin also appears, as the’40s arrived, to have gotten into boxing management, including handling local fistic gladiator Baby Kid Chocolate.

Then World War II came, and on Dec. 3, 1942, at the age of 37, Edward Benjamin Jr. enlisted in the Army to fight for his country. He served as a private until being discharged in August 1945. Squatter’s enlistment records list him at a diminutive 5-foot-2, 149 pounds.

Squatter returned to his hometown after the war, and by the time he reached retirement age in the 1960s and ’70s, he became active in the New Orleans Old Timers Baseball Club, an organization dedicated to preserving the memory and history of local Negro Leaguers. Benjamin participated in several of the club’s reunion all star games, in fact.

Edward Benjamin Jr., nicknamed “Squatter” for most of his life, died on Dec. 4, 1984, at the age of 79 and was buried at Corpus Christi Church.

Thus past into history one of New Orleans’ countless colorful segregation-era African-American athletics legends, but because of his college education, his service as a teacher and his valorous service during World War II, Squatter Benjamin perhaps holds a special place in local sports history.


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