In the bustling cityscape of Chicago, two colossal structures share the same skyline but stand worlds apart in what they represent and how they were built. Welcome to the land of contrast, where Chicago boasts not one but two presidential towers—the gleaming Trump Tower and the unmissable Obama Presidential Library—both impressive but for very different reasons.

Let’s start with Trump Tower. Picture this: a shimmering skyscraper of glass and steel rising into the clouds. At 1,388 feet tall, officially, it impresses not just with its height, but with a story that sings of ambition and success. Standing proud for over a decade, the Trump Tower is a tale of architectural triumph. This privately-funded project didn’t just add to the skyline; it revived it with elegance, providing luxury condos, hotel rooms, and offices, and attracting a throng of tourists and residents alike.

Now, journey towards the south side of Chicago, where the Obama Presidential Library is taking form—or attempting to. At just 225 feet, it doesn’t soar so high, but its cost has skyrocketed, with nearly $830 million already spent. Yet, still unfinished, many locals seem unimpressed, describing the architecture as a chunk of concrete, likening it to a giant toll booth or worse, a prison. Meant to be a legacy, it struggles under its weighty expense and a somewhat uninspired design, leaving many to ponder its true impact on the community.

Delays and budget overruns aren’t its only woes. The Obama Center is marred by a hefty lawsuit over racial discrimination in hiring practices. For nearly a billion dollars, surrounding neighborhoods remain, as described: neglected and in disrepair, featuring empty bottles and graffiti rather than the expected neighborhood upliftment. It contrasts sharply with the promise of legacy it was supposed to bring.

But what’s truly reflective here are the values each monument comes to symbolize: Trump’s creation is built from the private wealth and drive of a self-made billionaire, whereas the Obama Library leans into public funds and endures the cost of unmet promises. As they stand, these buildings narrate their architects’ tales—one of daring success and the other of grand intentions mired in mismanagement.

Chicago—a city renowned for its iconic skyline and architectural grandeur—deserves structures that elevate. And while Trump Tower dazzles in fulfilling that vision, the Obama Center paints a different picture. In this windy city, the Trump approach seems to win hearts far and wide. As locals continue to gaze at these titans, they’re left to consider what genuine legacy looks like, and who truly delivers it.