Photo by SCM Jeans
Pride Progress Flag
Pride Progress Flag
Since 2015 the Shepherd Express has recognized individuals, organizations and businesses that have made significant positive, lasting impact on the LGBTQ community’s progress in its struggle for equality. The awards represent all facets of the community from the arts, entertainment and education to social justice and philanthropy. Longevity of commitment is one of many criteria for the award. This year, several recipients have 50 or more years of dedicated engagement. Cumulatively, the eight awardees account for nearly three centuries of service. Their brief biographies and histories printed here cannot do justice to their contributions.
The Progress Awards dinner will be held Aug. 7 at Potawatomi Casino and Hotel. For more information, visit shepherdexpress.com/shepherdevents.
Activism: DA Leonard and W. Michael Ross
After meeting in 1984, DA Leonard and W. Michael Ross became inseparable. Upon the national recognition of marriage equality, they married in 2016. Ross passed away in 2024. Their relationship was not only personal but also one of common commitment to their LGBTQ community. As members of the National Association of Black and White Men Together’s Milwaukee chapter, both served on its board in various capacities with Leonard also serving on the national board. Ross, as “Miss Echo Chambers,” performed at NABWMT’s national conventions as well as locally and was first to win the title “Miss Black Gay Wisconsin.” Following the Dahmer killings, he served on a committee to enhance police LGBTQ training. Leonard participated in groups ranging from SSBL to Dignity Milwaukee. Through the UWM-LGBT Resource Center, Ross and Leonard endowed a scholarship that has dispersed nearly $100000.
Arts: Dale Gutzman
Dale Gutzman, impresario, playwright, actor, director and novelist, made his artistic mark on Milwaukee’s cultural life over several decades. However, his contributions to the city’s queer stage scene are among his greatest achievements in the cause of LGBTQ progress. Opening his 40-seat black box Off the Wall Theatre at the end of the 20th century in the heart of Milwaukee’s theater district, he quickly became (in)famous for his quirky, idiosyncratic and, more often than not, queercentric interpretations of the masters. Unbridled and unapologetic, whether Moliere, Shakespeare, Brecht, Williams or Chekhov, his own works or reworks (his drag version of Mommy Dearest), our “tortured genius” as a critic once called him,offered his LGBTQ and non-LGBTQ audiences a mirror and a looking glass. Closing OFW in 2020 under the duress of the pandemic, Gutzman turned to writing novels, over a dozen in all, based on gay themes and characters.
Business: Bill Wardlow
When Bill Wardlow moved to Milwaukee from his hometown of Waterloo, Iowa, he immediately became involved with the local LGBTQ community. That engagement grew exponentially over the years. After a stint as a popular bartender, in 1998 he and a business partner opened Fluid Bar in the heart of the gayborhood on South Second Street. Eventually, he became sole proprietor and made his establishment into a welcoming social hub. As one of the founders of the Milwaukee Metro Tennis Club, the sponsor of a SSBL softball team, host of countless holiday parties, drag events and fundraising charity benefits for a myriad of causes, Wardlow touched Milwaukee’s LGBTQ community with his positivity, generosity and humanity. He currently serves on the Wisconsin LGBT History Project advisory board. Wardlow was recently recognized with a City of Milwaukee Mayoral Proclamation for his enduring public advocacy.
Education: Jeffrey Morin
Jeffrey Morin’s over 10-year long history as Milwaukee Institute of Art and Design president is highlighted by a litany of successful diversity programs, partnerships and strategic outreach to underserved communities. Among them are the establishment of MIAD’s Equity and Inclusion Center that includes a collaborative partnership with Milwaukee’s LGBT Community Center. In fact, 60% of MIAD’s student body identifies as LGBTQ+ with 25% as transgender or nonbinary. Under Morin, MIAD also nurtured a partnership with LGBT milWALKee’s House of History. In 2024 the Wisconsin LGBTQ Chamber of Commerce named MIAD “Nonprofit Business of the Year” in recognition of these programs. Among his many professional affiliations, Morin is a member of LGBTQ Presidents in Higher Education. In a 2022 interview Morin succinctly expressed MIAD’s mission, saying “We are teaming with creatives who live with courage, integrity, and kindness. And we are genuinely committed to inclusion, innovation, and community.”
Equality: Pathfinders
Founded in 1970, Pathfinders began as a shelter for runaway and homeless youth on Milwaukee’s Eastside – a program that still exists today. Over the years, Pathfinders expanded its services to include Q-BLOK, a specialized housing and support program dedicated to homeless LGBTQ youth and their allies. Youth street outreach and a drop-in center provided basic needs services, homelessness prevention, mental wellness and help with employment and education. Since then, Pathfinders’ programs have continued to expand to include specialized support for youth experiencing trafficking, those aging out of foster care, parenting youth, those with high mental wellness needs and many more. Today the non-profit organization serves over 1,000 youth annually and remains committed to its mission to ensure young people are “safe, healthy, independent, successful and valued.”
Philanthropy: Maria Cadenas
In Spring of 2005 Maria Cadenas became Cream City Foundation’s executive director. During her tenure Cadenas expanded CCF’s mission. In addition to raising funds for LGBTQ community organizations, CCF itself become an instrument for social change to generate equality and build community. She was especially engaged in addressing the common goals of people of color and the LGBTQ community. Her efforts succeeded in creating seven new donor advisement funds and three targeted funds for the arts, athletics and youth. In 2008 CCF launched “Gay Neighbors,” a billboard, poster and web campaign that sought to give Milwaukee’s greater population insight into LGBTQ lives and issues. Under her leadership and fund raising, over $72,0000 was distributed to LGBTQ programs with an additional $200,000 disbursed through a partnership with the Greater Milwaukee Foundation. Upon her departure in 2011, Cadenas left CCF with assets of over $850000.
Pioneer: Diane “Legs” Gregory
A native Milwaukeean, Diane “Legs” Gregory has been a dynamic force in Milwaukee’s LGBTQ community for decades (over five, in fact). Ever since her first foray into The Factory, that infamous gay bar on Broadway, she has immersed herself in Cream City’s queer life. She performed as an entertainer and dancer in countless shows at every club that had a stage, tended bar and played softball for the Beer Garden, a popular women’s spot in the 1970s. In 1985 she joined Fest City Singers. Her joyful experience singing with that group soon shifted to the somber reality of performing for funerals for the victims of AIDS. Her advocacy and service in their varied manifestations are notable, too, for their unifying of the gay and lesbian communities. In 2023 Gregory received a commendation from the Milwaukee County board of supervisors. Today she is a member of the Wisconsin History Project’s board.
