CAA Sports has signed two-time heavyweight world champion Anthony Joshua to a commercial representation deal struck in partnership with the fighter’s 258 Group, according to Deadline.
As part of the arrangement, 258 Group Managing Director Freddie Cunningham joins CAA Sports Talent Group as Head of Client Strategy. Based in London, Cunningham will oversee Joshua’s commercial activities across endorsements, speaking and publishing, working alongside 258 Group and its family office.
Cunningham will also support the agency’s athlete business development and growth across its international roster. He reports to Roman Di Somma, CAA Sports’ Head of International Talent.
Joining an International Roster
Joshua joins a CAA Sports client list that includes José Mourinho, Son Heung-min, Liam Lawson, Sky Brown, Cole Palmer, Gary Neville, Laura Woods, Kobbie Mainoo and Robert Lewandowski.
Ring Return Scheduled
Joshua (29-4, 26 KOs) turned professional in 2013 and has held heavyweight world titles on two occasions. He last competed in December 2025, when he stopped Jake Paul in the sixth round of a bout streamed on Netflix from Miami.
Later that month, Joshua was involved in a car crash in Nigeria that killed his personal trainer, Latif Ayodele, and strength coach, Sina Ghami. Joshua was injured in the incident, and the driver was subsequently charged.
He is scheduled to return on July 25, when he faces Kristian Prenga (20-1, 20 KOs) in Saudi Arabia.
Business Interests
Outside the ring, Joshua and 258 Group have built investments across technology, real estate, content production, and health and performance. He has held brand partnerships with companies including Under Armour, Audemars Piguet, Hugo Boss, Jaguar Land Rover, DAZN, EA Sports, Meta and Beats by Dre.
Following the CAA agreement, Joshua’s business interests, family office and in-ring matters will continue to be overseen by 258 Group. Communications remain with Soapbox, legal affairs with Level, and promotional matters with Matchroom Boxing.
