I truly thought the man was indestructible. Jack Roeser was going to live to be 486 so despite the fact he was 90, the news of his passing took me by surprise. Not even death could get the better of that stubborn old man. 
Jack Roeser was a walking paradox, oxymoron, contradiction, incongruence or whatever you want to call him. Take your pick – it doesn’t matter – he was impossible to predict. Tribune reporter Rick Pearson and I discussed him at length and we were no closer to figuring him out at the end of that conversation than we were at the beginning.
I must have spoken with Jack at least six times over the course of my journalistic career, and the one thing I can say with certainty is he was never boring. There aren’t many people who can move me to stunned silence, but Jack did it on more than one occasion.
One minute you’re having this utterly normal conversation about Otto Engineering and the next he’s launched into the kind of attack on gays that would curl your toenails. There’s homophobia and then there was Jack Roeser homophobia.
Some said those blistering diatribes were borne of having a gay son, but whatever it was, it’s something I’ll never forget.
His insistent assaults on Illinois Senator Mark Kirk were so far beyond the pale that I often felt the need to ask people to pray for his soul. There’s a difference between not liking someone and being bent on their complete destruction.
Then, in Jack’s mind, the only thing worse than homosexuals, were the teachers. Oh lord! All you had to do is mention “teachers union” and you’d better be prepared to hold the phone a full six feet from your ear.
One can only surmise that, sometime in his youth, some errant educator had the audacity to tell Jack he’d never amount to anything and he never forgot it. Again, there’s a difference between being disappointed and a blood lust that would make a pitbull flee in terror.
To make matters worse, Jack couldn’t pick a political winner to save his life. Taking nothing from his painstaking business success, he didn’t understand that Rome wasn’t built in a day. His fervent belief that the liberal application of cash could change the political conversation overnight would only lead to frustration and disappointment.
For better or worse, Jack Roeser was a portent of exactly where the Republican Party was going.
But then there’s the side of Jack that very few people knew about. Occasionally, during our semi-frequent conversations, he’d let me in on it.
While morons like Papa John’s CEO John Schattner insist they’re under no obligation to share their good fortune with the very employees that made the company, Jack Roeser believed in the trickle down theory.
He laid the financial groundwork for many of his employees to buy their first home. It didn’t matter who or what you were, if you could do the job, Jack would hire you. If you were Hispanic and willing to work, Jack provided the opportunity to learn English free of charge.
When you worked for Otto Engineering, within the bounds of reason, you were family.
Unlike so many Republicans, Jack understood his success came at the hands of the many dedicated souls who preceded him. He could’ve cut a deal to take Otto Engineering anywhere, but he never forgot the community that made it all possible.
Without Jack Roeser, a true philanthropist, Carpentersville would not be the city it is today. He clearly understood that success was a shared notion and it was utterly meaningless otherwise.
Even though his politics often made me clench my teeth (and other body parts), I have to admire the man for moderating in his old age. He stopped the attacks on gays, he finally listened to folks who told him that progress comes in steps, and as long as you were fiscally conservative, he financially supported moderate Republicans for whom even I could cast a ballot (Jack Cunningham).
So I can only imagine St. Peter’s response as he watches Jack confidently saunter up to the Pearly Gates. I’m sure his initial reaction will be to send him packing, but upon a brief reflection, he’ll simply say, “Holy fuck! The last thing we want is for you to start encouraging and organizing the ‘other side.’ You may as well C’mon in.”
As for me? I fervently hope that Jack Roeser finally finds the peace and contentment he never found in this life.
Jack was a great example of the “self-made man.” He started Otto Engineering in a garage in the early 1950s, he told me with $6,000, and built it into a multi-million dollar company. He restored and rebuilt several classic limestone factory buildings down by the Fox River in Carpentersville to house his business, then began rehabilitating houses in town to provide good homes for the town’s residents.
His one great passion was sailing his yacht, the JENNINE, in the annual Chicago to Mackinac
race for sailing ships of all classes. He always returned home tired, but refreshed.
I am proud (and lucky) to say I knew Jack Roeser for twenty years, and that he was a friend and mentor to me, as well as my political guru. The door was always open and the coffee was always as
hot as our political discussions.
The end of a great conservative Republican, but I hope, not the end of an era.