The transgender community – locally and abroad – suffered a major loss this week when Diana Hemingway, a local activist and artist who has touched countless lives, took her own life on Dec. 20, 2016.  

Hemingway, 46, was known for her relentless activism around trans/queer issues, sex worker rights, disability rights, economic justice, racism, and issues impacting the kink community.  She exuded selflessness and compassion, particularly toward other trans and queer individuals who existed alongside and outside of the margins.  In the days following her death, an outpouring of love came from the community, including those who said that Hemingway was many things to many people.  

Some said that she had saved their lives and was there for them when nobody else was.  Others are angry and shining a spotlight on the fact that as a community, we failed her.  

Hemingway was born in 1970 to an Irish Gypsy family who traveled across the U.S. while working in the carnival business.  Through this experience, she developed an early mastery of folk and indigenous jewelry making.  Her family later settled in Fort Lauderdale, where she eventually began working for Greenpeace.  In 1989, she left for college to study photography, and got to work alongside famous landscape photographer Michael A. Smith.  She began to face new hardships, and left the art scene to explore other career paths.  

Hemingway was proud of the diversity of her lived experience throughout her 20s, 30s, and early 40s — prominent environmental activist, ordained minister, master auto technician, code enforcement officer, thrift store operator, and eventually, director of a local HIV testing program created to specifically serve the most marginalized of the transgender community. 

Sadly, Hemingway’s exploration of her sexual orientation and gender identity (especially as a genderqueer transfeminine person), caused her to lose several families and to encounter job discrimination.  This drove her back in the direction of art and activism.  In her own words, her photography and her art, as well as the way she lived her life, was meant to “connect the intersections of gender identity, sexuality, disability, feminism and sex work,” and to “advance understanding and empathy for the multiple oppressions” that she and others faced.  

In recent years, Hemingway struggled greatly with unemployment and underemployment.  

Though she had decided to embrace and utilize her gifts in sensuality (which she referred to as her “greatest art”), and had created her own business as a trans escort and fetish provider, Hemingway was fraught with trying to make ends meet every month for almost two years.  

She continued applying and interviewing for jobs in the non-profit sector on a regular basis, especially in the last year.  However, she was also very open on social media (and even in job interviews) about her history of sex work, her struggles with depression and suicidality, and her life as a neuroatypical person on the autism spectrum.  Despite wanting desperately to work again, she found that she simply could not get hired.  

Those who knew Hemingway have shared that she was a brilliant mind, full of knowledge, trivia, and history.  She was a nuanced thinker and someone who sought constant stimulation.  

In 2016, Hemingway shared with her partner, Landon Woolston, that she felt like she was deteriorating from the inside out as a result of not having access to gainful employment and health benefits. 

Despite feeling despair around no longer being valued by her community — the very community that she had fiercely supported and worked so hard to become a visible part of, she soldiered on.  At the urging of her partner and friends, she had begun working with a reputable therapist and taking antidepressants; she told others in recent months that she was feeling the best she had ever felt, but she also expressed that it was “too little too late.”  

After several crushing job rejections from local LGBTQ organizations in 2015 and 2016, Hemingway had deemed herself “unemployable,” noted that she was running out of resources, and saw herself facing homelessness again in 2017.  Hemingway also developed what she believed to be a bowel obstruction just a week prior to her suicide.  She told Woolston that she was worried not only about the medical procedures involved, but also the associated costs of treatment for the obstruction, as Hemingway did not have health insurance. 

Woolston, a prominent queer/trans activist and LGBTQ youth worker in Miami-Dade, began blogging about this devastating loss almost immediately as a means of catharsis.  He shared not only his grief but also his frustration with the failures of multiple systems and organizations to support Hemingway — especially when she openly expressed on social media her need for formal employment and desire to leave sex work, and was capable and hopeful that she could contribute to our community again.  

Woolston said in his blog on Dec. 24, 2016, “If you’re wondering what pushed her to leave us, know that the primary reason was fear of losing the life she had “worked so hard to build” (per her suicide note).”  Woolston later wrote a blog entry entitled “Raging Pain” that further addressed the struggles that transgender people, disabled people, and/or sex workers often face in trying to access employment -- even through organizations that purport to serve these very communities.  He said, “If Diana had gotten a job in the last six months, and especially one with benefits, I really do not think she would have taken her life,” and “I feel like if this loss doesn’t teach our local community the importance of hiring trans people (especially in the non-profit sector), nothing – and I mean NOTHING – will.” 

Hemingway signed her suicide note to Woolston, “Yours forever, In Love That Never Dies.”  To read more about their intimate partnership and to stay abreast of our community’s sweeping reaction to Hemingway’s suicide, visit Woolston’s blog at:

To get the most up-to-date information on the upcoming Celebration of Love event(s) for Hemingway, please visit:

If you wish to make a donation in Hemingway’s honor, please visit to donate to Project SAFE, a collaborative program founded by Pridelines and The Alliance for GLBTQ Youth to support LGBTQ youth experiencing or at-risk of homelessness in Miami.