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Chicago’s Decade-long Tug of War with Ex-President Trump

In what might be considered the zenith of a contentious relationship, Chicago and ex-President Donald J. Trump have been locked in a rather heated battle of words, with each party taking strong stances against the other. It’s intriguing to attempt to delve into why this former US leader and this vibrant city may harbor mutual animosity, and to explore this, I drafted a letter to Mr. Trump at his Mar-a-Lago estate, which is concurrently being published herein.

The letter was addressed to Donald J. Trump in Mar-a-Lago, Palm Beach, Florida, and it opened by addressing his consistent verbal tirade against our city. It has been over ten years of seemingly unwarranted criticism, and the intent behind this incessant condemnation remained unclear. After all, the city welcomed him, allowing him the privilege to construct a towering edifice along the river and let his name embolden its facade, visible for every downtown commuter.

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Yes, the citizens of Chicago do engage in playful social media banter involving this landmark, but it’s merely an innocuous part of our virtual camaraderie. We don’t believe this lighthearted jesting was ever a cause for personal grievance. Besides, your property here must have generated substantial profits. Chicagoan, Ed Burke, effectively assisted you on tax matters, despite his own legal issues.

Our city’s past leadership, exemplified by Ex-Mayor Lori Lightfoot, asserted that Chicago was a convenient platform for your political sparring. Can it be true that we were mere pawns in a larger political scheme? From the moment you announced your presidential aspiration, it seemed as though you were on a continuous hunt for adversarial entities to incite your supporters with heightened sense of threat these entities purportedly present for the traditional American lifestyle.

In one of the past debates, you controversially criticized immigrants dining on unconventional pets in Springfield, Ohio. It is worth noting that a considerable number of your followers are from rural and underpopulated areas. As a flourishing city, we have often been used in your narratives as a cautionary example to instill fear and derive political mileage.

We wonder if our predominantly Democrat preference during elections spews further fuel to your fire. However, this shouldn’t be misinterpreted as an affront against you. Our city has a history of leaning towards the Democratic Party, much like our enduring devotion for the Cubs or the White Sox. Presidential candidates from Reagan to Nixon have faced this political proclivity of ours.

Some boroughs in our city did resonate with your political views, like the law enforcement communities in Mount Greenwood and Edison Park, or the Orthodox Jewish population in West Rogers Park, appreciating your stance on Israel. These areas, therefore, might escape your critical assessments of our city.

Plainly speaking, Chicago has not seen a Republican mayor since 1927, perhaps adding another aspect to your displeasure. You could be leveraging our Democratic orientation to emphasize a narrative that cities under Democratic rule are afflicted with criminal activities. One such example was when you enlisted federal agencies and applauded a dip in criminal activities, which was already in progress prior to their intervention.

The litany of denunciations does grow tiring. Chicagoans harbor the hope that you will desist from using our city as a source of rhetorical ammunition. If you do secure another term and need a city to criticize, perhaps give Cleveland a thought. Their crime rate surpasses ours, and they’re well-seasoned to being on the receiving end of jokes.