[12] Wintrich was born Lucian Baxter Einhorn on 24 May 1988 in Pittsburgh, Pennsylvania, and grew up in Squirrel Hill, a residential neighborhood in the East End of the city.

[14] In the fall of 2005, while still in high school, Wintrich created the podcast "Acorns & Merlot," characterized by the Pittsburgh Post Gazette as "sometimes irreverent or crude [but] often hilarious.

[21][22] In 2016, Wintrich created “Twinks4Trump”, a controversial photo series that featured young, slim, and often shirtless gay men known as "twinks" wearing "Make America Great Again" baseball caps, which were associated with Donald Trump's presidential campaign.

Primarily shot in his East Village apartment, the photos were intended to challenge both the religious right and the progressive left, provoking discussions around sexuality, politics, and identity.

[27] Wintrich's photos served as a backdrop for speeches delivered by controversial figures such as Pamela Geller, Geert Wilders, Jim Hoft, and Milo Yiannopoulos.

[1] In an op-ed for The Art Newspaper, Dan Duray derided Wintrich's work as "Ryan McGinley but without any sense of balance, colour depth, technical acuity, texture, lighting, warmth, joie de vivre, basic humanity and sexiness, and add Make America Great Again hats.”[30] In an op-ed for The Hill, Wintrich stated that he was dismissed from his position at Anomaly for his political views, and had been up for a promotion before his dismissal.

[24] Featuring an array of artists and contributors, notable pieces included paintings depicting George Washington and Martin Luther King Jr. donning pro-Trump hats, and an "Emotional First Aid Kit” contributed by James O'Keefe.

[33] Initially slated to take place at Boiler (Pierogi Gallery), the event encountered a setback when the owner, Joe Amrhein, canceled his contract with Wintrich.

[24] In an interview with Artnet, Amrhein expressed his change of heart, stating that although he initially found the idea of a satirical show about Trump appealing, he believed Wintrich's genuine belief in the cause made it impossible for them to proceed.

[25] Originally, Wintrich intended to donate 30% of the art show's proceeds to the American Military Partners Association, an LGBTQ veteran group, but they declined the contribution.

[38][23][33] While attending the Republican National Convention in early 2016, Wintrich had befriended Jim Hoft, the founder of St Louis based publication Gateway Pundit.

[44] He spawned the "#FireColbert" movement, wherein he characterized the night show host's joke involving Trump and Vladimir Putin in a gay relationship as a "disgusting 12-minute homophobic rant"[45][46] He frequently used social media to criticize and mock mainstream press outlets for having what he perceived as biases and shortcomings.

[18][13] In August 2018, Wintrich engaged in a debate on America First, an online show hosted by Nick Fuentes, tackling immigration and anti-white racism.

"[58] On November 28, 2017, Wintrich was arrested after an altercation in which he, as an invited guest speaker, was lecturing at the podium, when a woman came up heckling and ultimately snatched the written copy of his speech directly from the lectern during a talk at the University of Connecticut entitled "It's OK to Be White".

[65][66][67] In February 2018, Wintrich tweeted the conspiracy theory that some survivors of the Stoneman Douglas High School shooting, who had spoken to the media about gun control in the wake of the tragedy, were "trained actors who were recruited by [George] Soros-linked organizations as spokespeople after a crisis.

"[68] The tweet was liked by Donald Trump Jr. but was much criticized by others, including shooting survivor David Hogg, whom Wintrich accused of being "heavily coached" for interviews.