From 1996 to 1997, Yoshino served as a law clerk for Judge Guido Calabresi of the U.S. Court of Appeals for the Second Circuit. In 1998, he received a tenure-track position at Yale Law School as an associate professor, and in 2003 the school bestowed a full professorship. In 2006, he was named the inaugural Guido Calabresi Professor of Law.[3]
His first book Covering: The Hidden Assault on Our Civil Rights was published in 2006. It is a mix of argument intertwined with pertinent biographical narratives.[4] His second book, A Thousand Times More Fair: What Shakespeare's Plays Teach Us About Justice was published in 2011. In 2016, his book Speak Now: Marriage Equality on Trial was published and received the Stonewall Book Award's Israel Fishman Non-Fiction Award.[5]
During the 2006-2007 and 2007-2008 school years, he served as a visiting professor at New York University School of Law, and in February 2008 he accepted a full-time tenured position as the Chief Justice Earl Warren Professor of Constitutional Law.[1]
In May 2011, Yoshino was elected to the Harvard Board of Overseers, where he served a six-year term.[6] In 2023, Kenji Yoshino joined the Facebook Oversight Board.[7] In July 2023, following a recommendation from the oversight board to deplatform Cambodian head of state Hun Sen, the government of Cambodia listed Yoshino as one of 22 people connected with Meta who were banned from entering the country.[8]