Sometimes everything comes together, and who doesn’t love that. Putting out an APB for new painting locations on Facebook, my good friend Conor McClintock and his lady Crystal offered up their downtown Chicago Carriage House lodgings – drinks included. With a place to stay lined up, I managed to secure a plane ticket for $110 – bully.

Finally, there was the critical detail of landing an indoor location with a view. From late 2004 to mid 2006, I worked as a Legal/Development Associate for The Trump Organization. There, I immediately joined the team responsible for financing Trump International Hotel & Tower, Chicago. In 2005, I visited the IBM building to review contracts alongside luxury residential specialist, Tere Proctor – when the Trump Building was just a foundation at the foot of the river.

When I eventually left The Trump Org., I was sure to contact Tere and pass along my new contact information – she said be in touch. Well, I emailed her two days before my trip, and she responded within two hours offering a stunning view from unit 51A – which comes with a 5000 square foot sky terrace (!!!) Here is a stroke-for-stroke recap of my John Hancock Center painting from the Worlds 6th Tallest Building.

All set up, 51 stories above Chicago.

A rough sketch to nail down the essential compositional form.

Sticking with the recent trend of beginning with red, I started with the Hancock and worked my way down the canvas.

The basic skeleton of the canvas in place, quickly, I only had two days to nail this picture start to finish.

Beginning to lay down planes, starting with the shadows.

Quickly establishing the background colors of the entire canvas, I was sure to focus on the interesting water/sky horizon point… the best indication of the height from which I was painting.

For some reason, the sky was speaking loudly to me, so I decided to go for a higher level of detail, capturing the swirling clouds.

With many windows detailed, here is where I finished after day one – it was intense.

A view of this magnificent building from North Wabash looking up. It was an incredible experience to see something we worked so many hours on manifested in concrete reality.

Beginning the second day with details in a deep red/pink hue.

Creating a similar brown tone capturing the building immediately in front of the Hancock Tower… it was challenging due to the tonal similarities from plane to plane.

Capturing the details of the buildings in the background, carefully working small elements of the same color throughout the canvas.

Beginning to add the windows, primarily in the foreground.

Finally, the iconic X-Braces of the Hancock Tower, laid on top of the initial brown town which was set to capture the reflections of the buildings in the foreground.

Now, the fun part… mixing interesting reflective colors and adding the windows throughout the canvas. While painting a building over the course of multiple sessions, the windows take on the characteristics of a thousand blinking eyes.

Erin snapped a shot of me painting… the view was just incredible.

If you squint, you can see my apartment building in the Upper East Side of Manhattan.

Getting ever so close to the finish.

Complete! My first Chicago painting.

A zoom-in detail to view some of the marks more closely.

As you can see, some of the early drawing peeks through the clouds… there is something I love about roughness peering through polish.

And what would a painting session on a 5000 square foot terrace be without the obligatory reflection shot? I want to sincerely thank Tere Proctor, Conor, Crystal, Trump International Hotel & Tower and its wonderful, friendly staff for allowing me to experience the Windy City in first class fashion.