[1] He has written numerous plays,[2] while his reporting has appeared in The New Republic, Talking Points Memo, Chicago Tribune, Miami Herald, and ESPN, among other outlets.
Squire was a part of the Lincoln Center Lab and his comedy "The Great Black Sambo Machine" was presented there and at Ars Nova the following year.
Squire was commissioned to interview surviving Crypto- and Converso-Jewish residents, research, and collaborate to create what became A Light In My Soul/Una Luz En Mi Alma.
[7] Squire is the book writer for A Wonderful World, a world-premiere musical based on the life of Louis Armstrong, and told from the perspective of the musician's four wives.
The following year Squire was hired by installation art company Local Project and wrote the script Dreams of Freedom for the National Museum of American Jewish History in Philadelphia.
Many of Squire's plays have received enthusiastic reviews and revivals, among them To Whom it May Concern, which ran off-Broadway in 2009, Match Me, produced by the New York International Fringe Festival in 2005.
[13] His writing has been called "a true gem that deserves to be set apart from the rest" by The Drama Review, "brilliant" and "thoroughly entertaining" by Show Business Weekly, and "engaging and provocative" by critic Martin Denton.
[16] To Whom It May Concern was also produced off-Broadway in 2009 at the Arclight Theatre with a cast including: Israel Gutierrez, Matthew Alford, Nicholas Reilly, and Carmelo Ferro.
In 2009, Squire wrote the book for the children's musical Matthew Takes Mannahatta, called "refreshingly clever" and a "cheerful tribute to our multiracial, multicultural America" by The New York Times.
Squire is also a recipient of the Lila Acheson Wallace American Playwright Fellowship at The Juilliard School, and the two-time winner of the Le Comte du Nuoy Prize from Lincoln Center.
Squire also co-wrote "Confessions of a Cocaine Cowboy" which world-premiered at Miami New Drama a few months later to sold-out crowds and became the highest grossing play in the theatre's history.