In June 2021, Bennett released a memoir entitled Reborn in the USA: An Englishman's Love Letter to his Chosen Home which debuted at #1 on the New York Times Bestseller List.

[citation needed] Regular guests included Matthew McConaughey, John Oliver, Will Ferrell, and bands like The National, HAIM, and Jason Isbell, all of whom came on the show to discuss their footballing passions.

After becoming a cult hit on ESPN during the 2014 World Cup,[3] the duo signed with NBCSN to create a weekly half-hour television show "Men in Blazers" which covers the English Premier League.

His guests have included Will Ferrell, Laura Linney, DeAndre Hopkins, Killer Mike, Rory McIlroy, Niall Horan, and Alex Morgan.

[5] Season two premiered in the spring of 2020 and featured interviews with T. J. Oshie,[6] Auston Matthews,[7] Ryan O'Reilly,[8] Tampa Bay Lightning coach Jon Cooper,[9] and Victor Hedman.

He has created television specials with José Mourinho, Pep Guardiola, Jurgen Klopp, Steve Kerr, Arsène Wenger, Mauricio Pochettino, Kevin De Bruyne, Harry Kane, Virgil van Dijk, and Wayne Rooney.

[28] Airing weekly, each episode featured an interview between Bennett and a member of the cast of Succession discussing the series in anticipation of its third season.

In October 2022, Bennett partnered with Tommy Vietor of Crooked Media to produce a seven-part podcast series tackling the corruption and human rights controversies surrounding the 2022 World Cup in Qatar.

[30] Bennett has taped films with US Women World Cup winners including Megan Rapinoe, Alex Morgan, Crystal Dunn, and Lindsey Horan.

Season One co-hosts were Becky Sauerbrunn, Midge Purce, Megan Klingenberg, Andi Sullivan, Tierna Davidson, Alana Cook, and Nadia Nadim.

The podcast also features interviews with a variety of guests, including San Diego Wave head coach Casey Stoney and Washington Spirit forward Trinity Rodman.

[42] In 2018, he wrote an op-ed in the Washington Post about Wayne Rooney[43] A lifelong fan of the Chicago White Sox, Bennett threw out the first pitch on August 29, 2019.

[40] In 2014, he announced he would be becoming a naturalized US citizen based upon the United States men's national soccer team's progress in the 2014 FIFA World Cup.