Every Holiday season Boss Tom’s Machine remembered the humblest of voters, those who consistently returned the Machine to power by casting ballots for Goat candidates. Then casting them again at another polling station. Then casting them again across town. Then, when necessary, riding Machine-chartered busses to the most remote precincts in Jackson County to elect Goats to county office.

S. J. “Silvey” Ray was no fan of Boss Tom, and he used his gig as editorial cartoonist at The Kansas City Star to cut the Machine any time he got the chance.

“Judge” Henry F. McElroy learned his politics and his public accounting as a young boy in rural Iowa. When Tom Pendergast engineered his appointment as City Manager McElroy was over sixty years old, but stood tall, slim, and muscular, with the wiry frame and evangelical scowl of a country preacher. He rose to prominence in The Machine as an administrative judge for Jackson County – the same office where Harry Truman got his start.

The trouble for Boss Tom began long before the bean counters obsessed over his tax forms.

Boss Tom was determined that the Machine would continue the tradition of philanthropy established by Big Jim Pendergast when he was alderman of the West Bottoms, and the distribution of five-spots to hobo voters on election day wasn’t the Machine’s only charitable endeavor.

If you wanted to see The Boss, you had to go through old “Cap” Matheus. Elijah Matheus was a man of mystery, and his opaque biography made his authority imposing. Nobody knew much at all about the stern factotum who ran The Boss’ office. It was common knowledge that he was a former riverboat captain – thus the nickname.

Someone pulled the rug out from under Herman Epstein. One day he was an honest businessman pursuing a legitimate trade. The next day he was a bootlegger. The grandfather of Tom’s Town Distilling Co.'s illustrious co-founder, David Epstein, would have to wear the title, or find some other business.

Of all the sin palaces in Tom Pendergast’s town, Dante’s Inferno (Lorelai Lynn’s east side cabaret) took the prize for delivering the most surreal Saturday night a thirsty populace could demand.

While Boss Tom Pendergast made plenty of money off of vice, he also had a genius for turning a buck at his day job, or rather, any of his many completely legitimate money-making enterprises. Kansas City’s ambitious “Ten-Year Plan” provided the opportunity for Boss Tom to put his mark on the city in a way that nobody could miss.

Tom Pendergast showed up early for federal prison. The guards didn’t expect Tom until after 9:00 a.m., but Pendergast did an end run around the press and showed up early at Leavenworth Penitentiary without escort. The harried federal marshal had to race up from Kansas City to play his part in Tom’s introduction to federal service. Apparently, it was customary for powerful men to dance when Boss Tom called a tune. Even the frowsy-headed marshal had to skip breakfast to accommodate The Boss of Kansas City.

Basie First of the Blue Devils: Kansas City Stomps to New Swing Sound From Southwest Circuit!

Respectable Republicans of Kansas City were sick and tired of Pendergast Populism.They decided the bi-cameral legislature – with upper and lower houses resembling the U. S. Congress – was too beholden to Boss Tom’s corrupt machinations. A new city charter, conceived “scientifically” by urban engineers and supported by bankers and businessmen, was put to a vote. The new charter would put Boss Tom and his cronies out of business, and replace Tom’s figurehead mayor with a professional city manager with dictatorial power. The legislature would be replaced by a nine-man city council whose principal duty was to hire the dictator.