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Willard Says...

December 28, 2025

Running a successful office building part 2

On the northwest corner of Monroe and Clark sits the latest addition to a seemingly endless supply of new hotels in downtown Chicago: Hyatt Centric The Loop.

Prior to the hotel, this fairly nondescript building was one of the best kept secrets in the Loop.

The businesses and individuals who were fortunate enough to maintain an office in this property at some point during its 85 year run, however, know that not only was it one of the best run structures in downtown Chicago, but also a true model on how to successfully operate office building.

Established in 1927, 100 West Monroe was a supremely located building in the heart of Chicago’s Central Loop.

Historically, it has been best known for its “cow path” (more on this in a future blog) and being the location of Chicago real estate legend Arthur Rubloff’s original office.

While there were some rough patches over the years, 100 West Monroe was prosperous and well occupied by professional and entrepreneurial. I was fortunate to not only be the leasing agent there for 16 years, but also a tenant.

100 West Monroe’s sustained success all started at the top with the owner.

The building was controlled by a family partnership who purchased the property in the early 1960’s and maintained control until it sold in 2012.The majority of their ownership tenure was debt free and they were diligent about reinvesting some of their profits back into the property.

Every year, they would pick a specific area to update, whether it be the lobby, elevators, common corridors or mechanical systems.

They would always budget funds for improving vacant suites prior to leasing so the product would show at its very best to prospective new tenants.

Ownership also made sure to have a dynamic team working along side.

The property manager was a seasoned veteran who knew exactly what was needed to operate a thriving property. He always spent money wisely and maintained a positive relationship with both his tenants and staff.

He was tough when necessary, but was universally respected and genuinely well liked. Undoubtedly, his relationships formed over the years were a key reason why few tenants ever moved out and why there was virtually no staff turnover. The two building engineers were among the finest downtown.

Both were employed at 100 West Monroe for over 30 years and treated the building like it was their own.

In addition to their expert care and maintenance skills, most tenants came to view them as friends.

Not only did they know just the right temperature to set each office suite, but they also made it a point of leaning everyone’s name and about their families and businesses.

These small details helped make the building a nice place to be.The rest of the staff was stellar as well.

The security guards always greeted people by name every morning as they arrived and were always ready to chat about the game from last night, weather, politics and other world events.

The cleaning crew was incredibly dedicated as well, and the building always sparkled.

Outside contractors enjoyed doing work at 100 West Monroe and typically went above and beyond the call of duty in order to continue getting the business.

Working in this unique atmosphere made my job as leasing agent easy. Once the building hit 90% occupancy in 1999, there was no turning back.

We hit 100% in 2000 and never fell below 96% for the remainder of the building’s office history.

Sure, the location was an asset, but the strong ownership, dedicated management and wonderful staff all contributed toward tenants thoroughly enjoying their experience.

We may not have had the amazing views, modern features and amenities offered at other buildings, but no one could compete with our responsiveness, personalized touch and attention to detail.

Everyone got along incredibly well and worked together seamlessly. This trickled down to the tenants, who all coexisted like one big happy family.

When 100 West Monroe sold in 2012, the new owner elected to exercise a clause which gave him the ability to terminate all of the leases.

Most people never took it all that seriously, but it happened and shock and sadness soon followed.

It was the end of an amazing era.

I learned real estate at 100 West Monroe and more importantly, how to do things the right way.

As I run into former tenants today and ask about their new building, the one constant comment is that “it is no 100 West Monroe.”

If every building operated as well as this one did, the wild world of downtown Chicago real estate would be much more tolerable.