3. Derby Day

Jermain heads to the south coast and to Harry Redknapp's house to catch up with his 3-time former manager. The pair discuss when Harry first heard of a young 16-year old Jermain and how he signed him from Charlton to West Ham, sending him on loan to Bournemouth, scoring in his first 10 consecutive games. Harry talks about his time in the USA with Bobby Moore and also the importance of managers having a keen eye on the youth teams of their clubs and getting to know each player not just in and around the club but also on a personal level too. Harry also gives Jermain advice on how to deal with big stars - recalling when he signed Javier Margas after a had good World Cup, only for the Chilean international and his family to get extremely homesick a few month into the season, culminating with Margas fleeing through a bathroom window and on the first plane back to Santiago. Harry also talks about giving Nigerian star Kanu and England's Paul Merson leeway to train when they liked whilst at Portsmouth and Jermain and Harry reminisce about the mercurial talent that was Paolo Di Canio and the Italian infamously sitting crossed-legged in the penalty box whilst the game was going on around him. Harry also reveals how low he got when he was given the sac and the amazing circumstances around his leaving of Portsmouth, signing for their most bitter of rivals Southampton and then rejoining them after a few bottles of red with the the owner chairman Milan Mandarić.

Jermain and former SAS soldier Mark 'Billy' Billingham discuss leadership and team building in this bonus episode of Outside The Box. Billy advises Jermain on what good leadership is, what it takes to build a team, when to delegate and how to spot and deal with individuals that have professional or personal problems or issues within his squad. Billy also talks about his time in the military on missions, recalling a near miss in the field and how he coped with pressure situations including when he was leading a squadron that was outnumbered, surrounded and under heavy fire. Billy also talks about being the head of the counter terrorism unit during the London 7/7 attacks and how he used his training and experience to cope with a high stakes and high pressure situation with his team and the government looking at him for answers, action and strong leadership. The two talk about Jermain's time with England doing exercises with the Royal Marines and what Jermain took away from that experience, and, Billy recalls a tricky situation in Rome whilst working as a bodyguard for two bonafide A-list celebrities and the paparazzi.

Jermain speaks to former England international and ex teammate Sol Campbell about his journey from calling time on his playing career to becoming a football manager in the lower leagues. Sol talks about know he wanted to go into management in the latter stages of his career as he was an on-field coach for Arsenal and his centre-back partner of Kolo Toure. He also revealed the managers that he took the most from, Ossie Ardielles at Tottenham in how to deal with players, Gerry Francis also at Spurs with the focus on fitness, strength and conditioning and Arsene Wenger at Arsenal and the sports science and practices he introduced from Japan. Sol also talks about his two forays into management as the boss of Macclesfield, who he helped keep in the Football League and Southend during the pandemic. The pair also discuss the lack of opportunities for black managers in the game and Sol reveals that from thirty jobs he's applied for he's only had four interviews. Sol talks about his interview with England Under 21s and says that there needs to be more visibility and time on the grass for black coaches to gain experience and get more jobs at clubs.

Jemain is back where it all began for him when Harry Redknapp signed him as a sixteen year-old from Charlton Athletic as he heads to West Ham's training ground to talk to his former teammate and now the current Hammers Women's team manager Paul Konchesky. They talk about Paul's journey from finishing playing, his 8-month break where he could do all the things he couldn't as a professional - including skiing. Paul explains how he was taken on by West Ham as a defensive coach for the academy, moved to being a Loan Manager - looking after the players that are on loan at other clubs and then to assistant to the WSL team and now the manager of West Ham Ham women in the Women's Super League. Paul and Jermain speak about the differences in coaching and managing female players compared to boys in academies and senior male teams. They also discuss the importance of having different characters needed for a manager's coaching staff and in particular, for the women's game, to have a female coach in West Ham's Danielle Bowman who can relate and demonstrate to the players things that Paul and his male coaches might not be able to do. Jermain also praises Paul and his coaching team on the quality of the training session that Jermain watched and Paul asks him, again to come back and do a finishing clinic with the squad, he just needs to bring his boots next time.

In the final episode of Outside the Box, Jermain reflects on his journey to this point, looking back on what he's learned through the series and what he hopes to achieve in the next weeks and months. He's been informed that he has an interview to attend - his first - with the Chief Executive of Brighton and Hove Albion, Paul Barber who will put him through his paces in a simulated interview that will give Jermain the sort of experience he will need when he comes face to face with a chairman. The two meet in London and Barber grills Jermain on his plans: why he wants to manage, what his philosophy will be, what style of football will he play, who will be on his coaching team and what culture he'd like to set. Across a couple of hours they talk back and forth before Barber calls time and the pair review the process. After looking at some of the highs and lows, they depart, only for Jermain to find out that there are rumours linking him to a position with the Spurs first team, and for him to receive an important phone call.