I keep trying to get my head into the right place, but I don’t think I have it tonight. Too tired, too hung over, too distracted by other shit. I’m working on the last third of the Pineapple Primary, specifically the introduction of James Belcastro and the primary day itself.

It’s funny, Belcastro is some one that I had no inkling about until I started doing research for this project. He was called the King of the Bombers, and he is one of the worst murderers in American history. Over 100 deaths are attributed to his actions for the Chicago Outfit, and the number is probably much higher in reality.

Belcastro was pure evil. He didn’t care who his targets were; men, women, children, the infirm and the aged, they were all fair targets for him. He once chased down an African American lawyer that had tried to run for office in one of the Chicago wards. He forced the man’s car off the road and shot him to death on the sidewalk of a busy street. Seven men went up in front of the judge for that crime. Not a single witness came forward. Belcastro walked away clean, probably without even a blemish on his conscious.

The man was a monster that we have all but forgotten about. The people and events surrounding the Pineapple Primary are filled with stories like this. These are stories that the twenty-four hour cable news stations would love to be able to talk about. People like Big Bill Thompson and Diamond Joe would be  forever fixed into the consciousness of the viewing audience. The Bootleg Battle of the Marne would be a week long special for Fox News. But, because of the times, because of the context of these events and the violent time and place they happened in, they barely warrant a side bar note in a college history book.

Another thing I’m learning is that even thought the events of the Pineapple Primary aren’t even a century old, any information I can find is cloudy at best. The primary sources are locked away in the vaults of Chicago’s public library where they are yellowing with rot and age. Not that they could really be trusted in the first place. I’ve read a few of the primary sources for the death of McSwiggin, and their information is inconsistent and most likely wrong. One paper will say he died with 7 men, another will say 3. One paper will say he died on the spot outside the Pony Inn, another will say he died in a parlor of one of his associates. The print markets back in the 20s were cutthroat and a reporter might spice up a few details of an article for another thousand papers sold.

The secondary sources are even worse. I’ve found references to the Pineapple Primary placing the events in 1927 instead of 1928, to Capone bombing the mayor’s supporters (of which he was one), and so on and so forth. In most cases when the author couldn’t be bothered to do proper research, they just glazed over the missing information with a few obtuse lines and their own assumptions.

The further I dig with my research the more I have to rewrite. I only found out the other day that Thompson, the mayor of Chicago when all of this went down, had presidential aspirations and effectively stopped showing up to work after his candidates lost the general election following the Pineapple Primary. I had to restructure the ending of the book because of this. All of the changes I have to made because of new information have made the story better and helped to ground the surreality of what was going on in Chicago.

I know that I’m going to get stuff wrong, and that bothers me, but there is a point where I just have to suck it up and press on with the story and hope that the information I have is good enough for the job I need it to do. (Primarily: keeping me from looking like a total moron.)

I don’t know if it was pure naivety on my part to think that there would be better information on something so recent. But, I didn’t think that it would be this bad. As the world moves more toward digital information over print information, I’m horrified to think of the research inaccuracies that a generation raised on Wikipedia will produce.

Here’s a stultifying thought for you – with all the research that I’ve done about this specific period in Chicago history, I am probably now one of the foremost experts on the Pineapple Primary. Yeah. I’m not even kidding. One of the most bizarre moments in American history and some half drunk amateur comic book writer in Memphis knows more than people who are writing books on this stuff.


Still can’t get this going. My brain feels like it is filled with tar tonight.

The hell with it.

I’ll be back tomorrow.