Preparations for Tottenham Hotspur’s second season under Ange Postecoglou are well underway. Members of the first-team squad who did not participate at the European Championship or Copa America this summer, including Son Heung-min and James Maddison, reported to the training ground for pre-season last week and they have been joined by lots of new faces.
Archie Gray and Lucas Bergvall have met their peers for the first time, following moves from Leeds United and Djurgarden respectively, and there have also been significant changes to the coaching staff. Chris Davies was second in command last season, but his decision to become Birmingham City’s head coach has triggered a reshuffle. Matt Wells has been promoted to senior assistant coach, while Nick Montgomery and Sergio Raimundo have joined as assistant coaches. Mile Jedinak and Ryan Mason remain as assistants and Rob Burch is still in charge of the goalkeeping department. It means that, although Davies has left, Postecoglou’s backroom team has increased to six.
Postecoglou has never worked with Montgomery or Raimundo before, continuing a trend we have seen throughout his career. Instead of surrounding himself with the same faces for every job, the Greek-Australian switches things up.
“I like to work with new people, that excites me and challenges me as a person,” Postecoglou said when he was appointed in July 2023. “It’s been mentioned to me that, apparently, I’m getting a bit old, so I’m surrounding myself with younger guys. But, more importantly, really bright, talented and ambitious guys.”
With a new support system in place, can Postecoglou and Spurs reach new heights this season?
Wells has a long history with Tottenham. His grandfather, Cliff Jones, spent 10 years at White Hart Lane as a flying winger between 1958 and 1968, making over 300 appearances for Spurs and winning five major trophies, including the league and cup double in 1961.
Unsurprisingly, Wells dreamt of following in Jones’ footsteps and joined Tottenham’s academy when he was nine before spending over a decade with them. However, his progress was disrupted by injuries, so he switched his focus to coaching and earned his UEFA B Licence at the age of 20.
Wells worked in Stevenage’s academy and for the Nike Academy until an opportunity arose to return to Spurs, where he supported Ugo Ehiogu with the development squad. He worked alongside now Ipswich Town head coach Kieran McKenna in a hybrid role that involved coaching and video analysis. During his time at Hotspur Way, he was heavily influenced by John McDermott, who became the Football Association’s technical director in 2021.
Ryan Mason and Matt Wells are both graduates of Tottenham’s academy (Nick Potts/Getty Images)
“My biggest takeaway was the importance of player development and how an individual-based philosophy can help footballers thrive,” he said in an interview with the Premier League in 2022.
“When I was planning sessions for the under-18s or under-23s, I was taught the value of asking yourself, ‘Who is training today?’ and ‘What do our most-valued players need?’. The priority was to build on the strengths and rectify the weaknesses of those players we felt could make the transition to Mauricio Pochettino’s first team.”
Postecoglou’s squad contains lots of young players, including Gray, Mikey Moore, Destiny Udogie, Pape Sarr and Micky van de Ven, so Wells’ passion for development is valuable.
Wells’ career changed course when he met the former England international Scott Parker. He assisted Parker with Tottenham’s under-18s during the 2017-18 season and they quickly forged a strong bond. Parker joined Fulham’s backroom staff in July 2018 and seven months later was appointed as their caretaker manager following the dismissal of Claudio Ranieri. Parker could not prevent Fulham from being relegated, but he secured the job permanently and hired Wells as his assistant.
Fulham returned to the Premier League at the first attempt after beating Brentford in the Championship play-off final, but were then relegated within 12 months, prompting Parker to leave by mutual consent and take over at Bournemouth. Parker and Wells achieved their second promotion together at Bournemouth but lasted only four games of the 2021-22 season. They then had a brief three-month spell in Belgium with Club Bruges.
Wells would often lead training and came up with different drills to keep players stimulated. He played a key role in deciding which tactical approach to use at all three sides. One source who worked closely with him, and wishes to remain anonymous to protect relationships, said “the players and staff adored” Wells. “He has good people skills and is an exceptional coach. Very methodical and detail-orientated,” they added.
When Mason became Spurs’ interim head coach towards the end of the 2022-23 season, Wells assisted him. There was no guarantee he would stay when Postecoglou arrived. Wells flew out to Italy to visit him and they spent four hours together. “I came away from that conversation so invigorated, inspired and desperate to be a part of (the team),” he told Tottenham’s podcast.
Wells has a real passion for coaching and tactics, and is incredibly highly rated at Spurs, as he has been at his previous clubs. Colleagues down the years have noted the high standard of his training sessions and meticulous attention to detail. He oversaw many of the open-play sessions at Spurs last season.
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Montgomery and Raimundo are the newest additions to the coaching staff. Montgomery spent the bulk of his playing career with Sheffield United and then moved to Australia in 2012. He played for the Central Coast Mariners (CCM) for five years before hanging up his boots at Wollongong Wolves. Shaun Mielekamp spent nine years as CCM’s chief executive before he left in February to take up a different role at rugby league side Wests Tigers.
“The first time I met Monty he was captain and played a pivotal part in leading the culture of the club,” Mielekamp tells The Athletic. “But we were in a dire state. We were strapped for cash, crowds were down, there was a high turnover of coaches, we were finishing towards the bottom of the table and not much talent was coming through the academy.
“He was very motivating and clear on professionalism. He didn’t relent just because the team weren’t playing well. There was no backing down from the standard he expected.”
Montgomery spent two seasons with Wollongong Wolves and juggled that with a coaching role in CCM’s academy. Around this time, Montgomery and Raimundo met each other on a coaching course in Belfast.
Raimundo grew up in Lisbon and after finishing college spent three years as part of Portugal’s navy and special forces. He then found a job in Benfica’s academy and worked with some of the best talent they have ever produced, including Bernardo Silva and Joao Cancelo. Raimundo worked in Brazil, Senegal and Canada before Montgomery convinced him to relocate to Australia. He speaks multiple languages, including French, which will allow him to connect on a deeper level with the different members of Postecoglou’s squad and relay urgent messages quicker during games.
Montgomery won the A-League with CCM as a player and as a manager (Steve Christo/Getty Images)
Montgomery and Raimundo set up their own coaching programme called the Football Grounds for kids between the ages of nine and 16 who had failed to make it into an academy. The pair played an influential role in developing talent within CCM’s own youth setup, too. They worked with Alou Kuol, who went on to join Stuttgart in Germany, his younger brother Garang, and Josh Nisbet.
Garang Kuol signed a four-year contract with Newcastle United in September 2022 and became the youngest player since Pele to appear in the knockout stages of a World Cup later that year when he came off the bench in Australia’s 4-1 defeat to France. Nisbet made his debut for Australia in March 2024.
Montgomery gave an insight into his coaching philosophy last year when he told the Sydney Morning Herald it was “like being a teacher”. “Coaches that look for the finished article, they’ve either got too much money or they’re lazy,” he said. “You have to develop them by giving them opportunities, playing them and working with them on the training ground.
“When I got into coaching, I wanted to be classed as a development coach — and that’s not just young players, that’s older players, too. The whole point of being a coach is to improve people. Every player we look at, we see the person first, and then the player and what we can turn that player into.”
In July 2021, Montgomery and Raimundo were entrusted with taking over the first team. They were “brave with recruitment” and “immediately brought a real attacking flair” according to Mielekamp. “In the A-League, you’re allowed five foreign players in your squad and rather than getting established players from the Eredivisie or Championship, they focused on younger talent,” he says. “It brought a buoyancy and enthusiasm to the side and complemented what was coming through the academy. It was a perfect blend.”
CCM finished fifth in Montgomery’s first season in charge. They were runners-up in the 2022-23 campaign and qualified for the A-League finals. They beat Adelaide United 4-1 on aggregate to set up a final against Melbourne City, who are a part of the City Football Group which includes Manchester City, Girona and New York City.
Melbourne had finished top of the regular season standings three years in a row. CCM thumping Melbourne 6-1 was not in the script. CCM claimed their first trophy in a decade and the story is being turned into a documentary.
“What Monty and Sergio delivered on the field was truly remarkable,” Mielekamp says. “I was crying. Nobody saw it coming apart from them. They were confident, knew exactly what to do and the players executed it. I remember giving (Monty) a hug on the field after. The underdog with no resources took on the might of the City Group. It’s a special part of my career.
“So often coaches leave and things crumble. But it has continued under Mark Jackson. They have won the treble and it has flowed on from Monty and Sergio’s work.”
In September 2023, Montgomery left CCM to become the head coach of Scottish side Hibernian with Raimundo following him. Hibs had finished fifth the previous season but kicked off the new campaign with three defeats and lost to Aston Villa in a qualifying match for the Europa Conference League group stage. Montgomery instantly set about changing their style.
Montgomery and Raimundo lasted just eight months at Hibs (Ross Parker/Getty Images)
“His first game was away against Kilmarnock and they were playing a 4-2-4 formation in possession,” Mark Atkinson, who reports on Hibernian for the Scotsman, tells The Athletic.
“When they had the ball the full-backs pushed high. He wanted to play out from the back and invite the press. That scared Hibs fans — they were not used to that philosophy.
“They rarely got caught out but a lot of the players were not comfortable on the ball. He told the players, ‘If you make a mistake it’s on me.’ The performances were encouraging but there were no statement victories. They weren’t taking their chances and weren’t keeping the door shut at the back.
“They went to Ibrox and lost 4-0 to Rangers. It showed a degree of naivety. Rangers had just sacked Michael Beale and we knew Ibrox would be energetic under their new manager (Philippe Clement). Hibs were so open it allowed them to score at will.”
Hibs went on a six-game unbeaten run following that defeat but in December their form nosedived. They went eight games without a win which included defeats at home to Rangers, Celtic, St Mirren and Hearts in the Edinburgh derby. Results improved across February and March but they failed to secure a top-six finish. A 4-0 defeat to Aberdeen at Easter Road sealed Montgomery and Raimundo’s fate (for context, Hibs are on to their sixth full-time manager in five years).
“It was an abject performance,” Atkinson says. “It didn’t have any structure or cohesion. Confidence was low and the team was littered with mistakes. There was a small number of fans who protested. They felt the team wasn’t progressing under him.
“But he was a hugely popular individual in the dressing room. He was excellent at managing players who had been ostracised by the previous regime. His one-on-one coaching, especially of attacking players, people really enjoyed.
“I just don’t think Montgomery showed enough flexibility in his tactical approach. They drew too many games and threw away leads. But I suspect what he did at Hibs, sticking to his principles despite poor results, Ange would have really admired.”
After a promising debut campaign, Postecoglou will be aiming to finish higher than fifth this time around. Losing Davies is a blow but Wells should be more than capable of filling the void. Montgomery and Raimundo will bring their own unique experiences to the coaching set-up and a track record of improving younger and older players.
There are a couple of areas of the squad that still need strengthening, but once that business is complete Spurs should be in a great position to seriously compete in the Premier League and Europa League next season.
