Renowned jazz singer Dee Alexander will headline Rainbow Railroad’s annual fall concert fundraiser, When I Am Free, Oct. 23 at the historic Jazz Showcase in Chicago’s South Loop neighborhood.
This end-of-year fundraiser has taken place in Chicago every fall for the past five years. The benefit concert has featured performers with strong Chicago ties who are also passionate about Rainbow Railroad’s mission to move many more at-risk LGBTQ+ individuals fleeing persecution around the world to safety.
Previous years’ performers have included the classical violinist Rachel Barton Pine, local and international jazz legend Patricia Barber, Grammy-winning artist Allison Russell and renowned songwriter and vocalist Ann Hampton Callaway.

Rainbow Railroad USA Board Chair Bruce Koff said, “We have cumulatively raised over $250,000 in support of Rainbow Railroad, which has allowed us to move many more people to safety. This year, we are thrilled to feature Chicago’s own Dee Alexander.
“Music critic Neil Tesser described Dee as ‘a true jazz diva in the mold of Sarah Vaughan, Dinah Washington and Dianne Reeves.’ She’ll perform with world-class musicians Junius Paul, (bass), Miguel de la Cerna (keyboard) and Ernie Adams (percussion). It really doesn’t get any better than that. It’s Dee’s concert, but we’ll take a few minutes to talk about Rainbow Railroad’s work and hear from one of the courageous newcomers to Chicago whom Rainbow Railroad has helped.”
Koff added that they decided to hold this event at the Jazz Showcase because it “is one of those places that is filled with decades of Chicago musical history. It’s a perfect venue for performers like Dee and creates an intimate setting to gather around both music and mission.”
Chicago has been Koff’s lifelong home where he has made his mark as an LGBTQ+ activist in many capacities. Since his retirement in 2018, he has dedicated his expertise toward raising awareness and funds for Rainbow Railroad. In 2019 Koff joined the board of Rainbow Railroad USA and subsequently became its chairperson.
Koff noted that Chicago has always been a city that has welcomed refugees from all over the world, which included his own grandparents. Now the city’s LGBTQ+ community “has this remarkable opportunity to make a real difference in the life of someone desperate to live authentically, thrive and contribute to the common good.”
When I Am Free will also celebrate Rainbow Railroad’s recent partnership with the U.S. State Department’s Welcome Corps program, which invites any five citizens or permanent residents to form a private sponsorship group to welcome and help settle a refugee.
“Rainbow Railroad created these Communities of Care made up of LGBTQI+ people and allies in order to ensure that newcomers fleeing anti-LGBTQI+ persecution are welcomed by individuals who are dedicated to their well-being,” said Koff. “Each team commits to support the newcomer’s resettlement for a minimum of 90 days. Resettlement includes help for the newcomer to establish a household with appropriate supplies and clothes and also find housing, employment, language classes and health care.
“Team members also orient newcomers to transportation, culture, community resources, shopping, recreation, banking, finances and assist them in completing all the preliminary documentation required to work and pursue permanent residency. It’s a full plate, but Rainbow Railroad provides guidance and resources every step of the way. In addition, we are particularly fortunate in Chicago to have partnered with Howard Brown Health, Center on Halsted and Refugee One to provide ancillary services.”
Koff said that, so far, 23 LGBTQ+ newcomers have been welcomed into the U.S. through the Communities of Care program, with six in Chicago and the others in Boston, San Francisco, Houston and Washington, D.C. There are now 46 Communities of Care across the U.S. and more will soon be established in Albuquerque, New York City, Sacramento, Palm Springs, Carbondale and Los Angeles.
“If someone in the Chicago area is interested in volunteering, they should contact Rainbow Railroad’s Engagement Officer here, Drew Heckman, at dheckman@rainbowrailroad.org,” said Koff. “Drew will explain how to join, create or support a Community of Care. Having served on a team myself, I can tell you that it is one of the most fulfilling and moving experiences I’ve ever had.”
Heartland Alliance Health Northside Food Program Founder and When I Am Free event host committee member Lori Cannon said, “It is my proud honor to have supported Rainbow Railroad these past seven years under the close watch and leadership of Bruce Koff. They have been a much needed lifeline to LGBTQI+ refugees and immigrants whose lives are under attack.”
Former Personal PAC CEO and President Terry Cosgrove and When I Am Free event host committee member said, “Supporting Rainbow Railroad is a magnificent way to help LGBTQI+ people who experience violence and oppression in some of the most hostile corners of the world. It is important that those of us with privilege seek out ways to help which is why I didn’t hesitate to be part of the event. Rainbow Railroad is a route to freedom. I am honored to help someone in need get to safety.”
Alexander said, “When we dare to love without despair and live without fear, we are free. I commend the freedom fighters of Rainbow Railroad and the people they serve. I am thrilled to perform for When I Am Free.”
Koff highlighted the critical importance of this event and noted that, “In approximately 60 countries around the world, we are criminalized for who we are or who we love. In these and other countries where same-sex relationships and/or trans identity are highly stigmatized, queer individuals are at increased risk for extreme violence, arrest, imprisonment, torture and even death. Inspired by the Underground Railroad, Rainbow Railroad helps move people in imminent danger to safety and, in partnership with over 25 different organizations around the world, provides an array of lifesaving assistance.
“When I Am Free is both an event and a promise,” Koff concluded. “The event gives all Chicagoans an opportunity to celebrate our progress through the spectacular music of one of the city’s greatest talents, Dee Alexander. It also gives us an opportunity to fulfill that promise for more people every year.”

