The Downtown Real Estate Softball League of Chicago held its 15th Annual Winter Classic Jan. 30. The outdoor game saw 35+ hardy athletes slipping and sliding in the snow in embodiment of the league’s spirit of camaraderie among commercial real estate brokers and industry colleagues. After the games, participants enjoyed an apres party at the River Shannon.
DRESL has been a staple of the Chicago commercial real estate community for nearly 50 years. Richie Klein, then with Metropolitan Structures, threw the first pitch on a Friday evening in Oz Park in 1978, and the rest is history.
In its inaugural season, DRESL consisted of brokers from LaSalle Partners (now JLL), Arthur Rubloff, Cushman & Wakefield, Coldwell Banker, Irvine Associates (at various times Buck/Irvine, Realsource, Prime, and HSA), Midwest Realty Exchange (MRX), which later became Grubb & Ellis, and Frain, Camins & Swartchild, which became Insignia and was eventually replaced by Golub & Co.
The league was an instant success, with brokers clamoring for their turn at bat. By 1983, DRESL had grown to six teams and outgrew its original Chicago Park District permit. By the mid-90s, the league had grown to 12 teams and moved to its current home at Lincoln Park – South Field with après-parties at the River Shannon. Today, there are 15 teams, including Colliers, CBRE, Marcus & Millichap, Bradford Allen, Stream, Dream Town, Transwestern, Clear Height, Golub, Avison Young, JLL, Advocate, Retailers, and Cushman & Wakefield.
What makes DRESL such a success isn’t where the brokers play ball or drink beer after the games; it’s the opportunity for them to come together to network in a casual, fun setting. There is friendly competition on the field and camaraderie in the bar. There are more brokers in one room (or on one field) than any other industry event, and it happens every Monday from May through mid-July.
“DRESL has been a labor of great love for me for decades,” said Richie Klein, founder and commissioner. “Back in ’78, I just wanted to play a little ball. I never thought it would grow to be what it is today.”
Before DRESL, there were no formal organizations for the commercial real estate industry. Animosity and unfriendly competition ran high and DRESL helped knocked down barriers. Playing ball together, spending time together outside of the office together in an informal setting allowed people to get to know one another and develop friendships beyond a purely professional level. Throughout the years, DRESL has seen folks get married, change companies, have children, retire. Landlord agents and tenant agents alike flocked to DRESL because it provided one-on-one connection that a lunch or coffee during the workday would never be able to replicate.
About 20 years ago, during DRESL’s upward ascent, sponsorships were introduced to the league.
“It seemed like a natural progression,” said Lee Golub, Golub & Associates, Assistant Commissioner. “We had great momentum, with numbers climbing every year and increased visibility among industry partners year over year. We wanted to provide another avenue for support to strengthen those partnerships through sponsorships.”
DRESL has had companies sponsor its après-parties ever since. Not only do they receive recognition among league participants, but they are also recognized weekly through DRESL Droppings.
DRESL Droppings, originally written via typewriter and disseminated via paper, was optimized in 2019 by Nathan Greenhalgh and Rightsize Facility. Today, it boasts a substantial subscriber base with consistently high open rates and a loyal, highly engaged audience. The seasonal newsletter features video (and bloopers), photos, game recaps, league standings, sponsor recognition, and upcoming industry events. Nathan Greenhalgh was recently promoted to Executive Director of DRESL.
The 2026 DRESL season begins on May 4, 2026, and there is still time to join and sponsor the league! Join the best commercial real estate group in the city today.
Email [email protected] to get involved with a team or to learn more about sponsorship opportunities.
