One hundred years ago my great-grandpa boarded a ship from Puerto Rico to Cuba to start a better life.  The Spanish-American war had ended, and the Americans that came to “liberate” us, had left the local economy in uhmmmm a challenging  state.  En route to Cuba, someone on the ship convinced him that going to Dominican Republic would be a better option, since non-blacks were the ruling class.  So, on the eve of the first world war, with no marketable skills except being white (or “not as dark” in his case), my great grandpa moved to Dominican Republic.  Initially as a ditch digger, but shortly after as an entrepreneur, drug dealer, and land owner.   My family recounts a slightly different version, but that’s the general gist.

You see, at the turn of the century, the US had entered the Caribbean en force.  They had won the Spanish-American war, and kept Puerto Rico as a military stronghold, while invading Dominican Republic to, among other things, control sugar production.  Having no refinery in DR, meant the sugar cane was cut and shipped back to Puerto Rico, where it would be processed and then exported to the US.  My great papa moved to the outskirts of La Romana where the sugar cane was weighed and shipped.  He started work as a ditch digger, but quickly moved up to landowner by way of drugs (then called moonshine and illegal in the US at the time).  This he sold to American troops stationed on the east coast, which was undoubtedly illegal if not by Dominican authorities, certainly by American laws.  (As far as I can tell, US soldiers cannot partake of drugs that are illegal in the US when deployed abroad.  But that’s all a footnote.)

How a ditch digger came to own a huge convenience store is a mystery, although family folklore says it was done through “hard work and diligent savings”.  Irregardless of the truth in our family story, what we do know is that little by little, the store profits were reinvested to buy a shit-ton of land at jaw-droppingly low prices.  Why would anyone sell prime real estate at a discount to the largest  sugar mill in the Caribbean is no mystery.  It turns out that Puertorican cops employed by the US army were hired to burn the lands of farmers who didn’t want to sell.  The farmers who weren’t directly “persuaded”, sold at a steep discount, afraid that they’d be expropriated if they didn’t sell.  Enter my grandpapa, who undoubtedly by his financial acumen I’m told, and not by being white or on the side of the men with guns (sarcasm intended), bought so much land over the next decade, that even I will receive a small yearly stipend when my mother passes on.

To my mother’s 65+ year old Californian eyes, she remembers being poor, and my grandma counting every penny.  But she also remembers having a house with land, and going to school in a horse-drawn carriage, whereas most children walked to school (if they did at all).  She remembers a modest house with modest means, but those were enough to send her and  my aunt to private schools both in Dominican Republic, and then in Puerto Rico.  The financial privilege may not have been immense, but when I look at third generation cousins, I see a disproportionate amount of success (doctors, lawyers, graduates from Yale, and a not-so-bad computer programmer)– all surrounded by a lot of darker skinned folk that weren’t as lucky.

Take the other side of my mom’s family (of much darker skin and without the inherited privilege of being US citizens in DR).  Their lands were outright taken by the sugar plantation, and they’re STILL in legal battles trying to reclaim the lands which they farmed almost a century ago.  When one of the great-great-aunts died recently, she lamented that she and her children were still poor, entangled in legal battles, while The Company was still tilling their land for a huge profit.

Privilege may not seem like a lot, but over generations it adds up.  Even though my mom never remembers being well off and the amount of money diluted among the grandchildren of the patriarch is small, at age 66, it still forms a non-trivial part of my mother’s retirement portfolio.

I don’t mean to single out one side of my family, since when you poke hard or far enough at most families, you inevitably dead end in wholesale theft disguised as financial acumen.

Take American land for example.  Through the Homestead Act of 1862, approximately 270 million acres, or about 10% of all the land in the US was given to over 1.6 million American families– virtually all of them white.  Today, research finds that about 20% of the US population can potentially trace their family’s history of building wealth to this one public policy.  The land was mostly empty… if you don’t count Native Americans, of course.  It turns out you can do an awful lot as a country, when you “inherit” an entire continent to (re)shape as you want.

So when I end up working in a silicon valley firm because I’m smart, I call bullshit.  There are plenty of smart folk cutting sugar cane.  Though it turns not everyone is lucky enough to have ancestors steal a bunch of land and use the proceeds to pay for school and other amenities I take for granted.

This isn’t to say I’m going back to the fields to work off my penitence, but that I’m trying to keep my privilege in check when judging others, voicing my opinions, or when stepping up to the ballot box.

What privileged skeletons are in your closet?