[5] Kinew moved to suburban Winnipeg with his parents in childhood and attended Collège Béliveau,[6] a French immersion school, and vacationed in Onigaming in the summers.

[8] Kinew began working in broadcasting after the Winnipeg Free Press published a letter to the editor which he had written about Team Canada hockey, and a local CBC Radio producer contacted him to express interest in creating and airing a documentary feature on the matter.

[4] In 2010, Kinew was a finalist for the Future Leaders of Manitoba award and lost to Canadian filmmaker and director Adam Smoluk.

[9] Other notable finalists of the award include Olympic champion Jennifer Jones, radio personality David 'Ace' Burpee,[10] friend of Bell Let's Talk Karuna (Andi) Sharma,[11] artist Kal Barteski,[12] and Canadian restaurateur and philanthropist Sachit Mehra.

[13] Kinew has been a reporter and host for the CBC's radio and television operations,[14] including the weekly arts magazine show The 204 in Winnipeg and the national documentary series 8th Fire in 2012.

[18] After being a member of the hip-hop groups Slangblossom and the Dead Indians[19] in the mid 2000s, Kinew released his debut individual CD as a rapper, Live by the Drum, in 2009.

In the book, Kinew details his point of view on several controversial matters related to his past, including convictions resulting from alcoholism, his assault of a taxicab driver, and misogynistic and homophobic lyrics from his music career.

[24] A reviewer for The Globe and Mail commented: "the undeniable significance of The Reason You Walk's message, and the fact that the book holds so much for both aboriginal and non-aboriginal readers, makes it a must-read.

[25] In 2018, Kinew published a children's book, Go Show the World: A Celebration of Indigenous Heroes, about notable figures in First Nations history, including John Herrington, Sacagawea, Carey Price, and Crazy Horse.

[32][33] Following an apology for his past comments, at the election on April 19, 2016, Kinew defeated Manitoba Liberal Party leader Rana Bokhari in the riding of Fort Rouge.

[34] He was subsequently named the NDP's spokesperson for reconciliation and opposition critic for Education, Advanced Learning, and Training, as well as for Housing and Community Development.

[24] On February 24, 2003, Kinew was arrested in Winnipeg, after he was spotted erratically driving his father's 2000 Dodge Dakota by Henderson Highway late in the evening.

A witness testified in court that they followed Kinew for several kilometres and saw him lose control of his vehicle twice after striking a guard rail and street light.

[53] In June 2003, Kinew was charged by the RCMP with two counts of domestic assault related to allegations that he threw his then-girlfriend, Tara Hart, across a room during an argument.

[54][55] These charges were previously unknown to most during Kinew's public life, only coming to light in 2017 via anonymous emails sent to Winnipeg media outlets.

[56] On page 70 of his 2015 memoir, The Reason You Walk, Kinew claimed he had grabbed a cab with friends and "hopped out without paying," after which:[24][T]he driver caught up with us and pushed me.

The police showed up and tackled me.It has been pointed out that Kinew's account of the incident in his book heavily differs from what was heard in court during his 2004 sentencing hearing.

[58] Kinew has gone through various exercises to rehabilitate himself from his issues with alcohol, including attending sweat lodges and a sun dance event where he fasted for four days and pulled buffalo skulls by piercings cut into his body.

[59] In September 2016, Kinew married Dr. Lisa Monkman, an Ojibway family physician who practises medicine at an inner-city clinic.