Music icon Madonna voiced her disapproval of the Trump administration's recent executive orders, particularly one impacting the transgender community's military service, in a message shared on social media platform X. Expressing sadness over perceived setbacks to freedoms fought for over time, Madonna included a pride flag and broken heart emojis, encouraging her followers to persevere in their advocacy. This post followed an executive order signed by President Trump restricting transgender individuals from serving in the military, a decision praised by conservatives but met with criticism from others.

Madonna, a long-time critic of President Trump, previously spoke out against his policies during his first term. In a 2017 speech at the Women's March in Washington, D.C., she made controversial remarks about the White House, drawing strong reactions from Trump supporters. After Trump's 2016 election victory, Madonna expressed her disappointment, likening the experience to a feeling of loss.

Another executive order issued by President Trump established a binary definition of sex (male and female) within the federal government, mandating adherence to biological sex. This decision further fueled the ongoing debate on gender and its recognition within government policies.