Kevin Thelwell began his winding career in football as a trainee at Crewe Alexandra, the small Cheshire professional club known for the prolific success of its youth academy under manager and director Dario Gradi. Though he never ended up making a professional appearance even after a switch to Shrewsbury Town, Thelwell would find a dramatically more ascendant career in the field of coaching. After gaining distinction as one of the youngest obtainers of the UEFA Pro License at only 25, he began working as a coaching administrator for the Football Association of Wales in the late 1990s before helping launch a structural overhaul that would lead to the tiny nation to an outsized position in the pecking order of European football.

By 2002 Thelwell had risen to become the FAW’s director of coaching education under technical director Osian Roberts, a visionary who applied methods learned from his years working the US soccer camp circuit to take the Welsh program to new heights. With Thelwell at his side, Roberts oversaw a massive forward leap for Welsh football infrastructure in which the organization developed the state-of-the-art training facility Dragon Park as well as a highly-regarded coaching course system. Using the structures built by Thelwell the FAW’s pro license course first attracted attention for its accessibility and development of Welsh coaches such as longtime Fulham director Kit Symons and the late Wales national manager Gary Speed. Though Thelwell left the FA for the club circuit in 2005, the coaching badge program he helped build had by the 2010s become highly popular with players from home and abroad such as Mikel Arteta, Thierry Henry, and Patrick Vieira.

It was in 2006 that Thelwell caught the eye of Billy Davies, the colorful Scottish manager then working at Preston North End. After being headhunted by Davies for the position of academy manager at Preston (making him the youngest professional academy chief in England at the time), Thelwell moved with the regime to Derby County the next year where he continued in academy work as well as an assistant coach with the first team. The Rams would achieve an unlikely first year promotion under Davies, and with optimism in the air it was notable that Davies and Thelwell explicitly looked towards North America for recruitment, with former Canadian international Colin Miller hired as coach/scout and American internationals Benny Feilhaber and Eddie Lewis signed to shore up the team for top flight action. However, that year Derby would endure what many consider the worst campaign in Premiership history. After serving briefly as caretaker following the sacking of Davies in November 2007, Thelwell would leave the club later that season.

Following this career low Thelwell would find his long-term home at Wolverhampton Wanderers, the tradition-minded West Midlands club known for its majestic stadium at Molineux and 1950s cup-winning heyday under visionary manager Stan Cullis before declining into an almost-constant presence in the English second division. Brought on initially as the director of the club’s academy, Thelwell would eventually shift to a position as director of recruitment where his sideswipes with the American game would continue as he oversaw the transfers of players such as Kevin Doyle and Jack Price to MLS sides. Thelwell and the club both saw a rise in fortune as Wolves, then a Football League Championship side, were taken over by new ownership in the form of Chinese investment firm Fosun International in 2016.

It was at this point that Thelwell’s role in the club wound up in an intersection of many of the streams currently defining modern European football. Upon the arrival of Fosun’s resources, the club tacitly acquired the services of Portguese superagent Jorge Mendes, best known for representing Cristiano Ronaldo as well as countless other high profile players and coaches throughout Europe. While on the face of things Thelwell was promoted to the role of full sporting director by Fosun, it was widely acknowledged that recruitment for the club’s first team was in largely in the purview of Mendes, who arranged the transfer signings of over a dozen of his own clients (mostly Portuguese and Brazilians) to Wolves over the coming years. While Thelwell had maintained day-to-day control of club technical affairs and youth development, his previously-selected head coach Paul Lambert was pushed out under pressure from Mendes to hire a new manager in his own client, Nuno Espirito Santo, who would go on to lead Wolves into the Premier League in 2018. Despite the friction, Thelwell’s contributions at Molineux were valued enough to see him added to the club’s board of directors under Fosun and chaiman Jeff Shi. Thelwell was evasive about the relationship with Mendes in an otherwise interesting and candid 2018 podcast interview about the nature of his role:

Jorge is an agent just like any other. We’ve taken some of Jorge’s clients but also taken clients from other agents. My perspective on it is we haven’t broken any of the rules, we are very clear on that and the EFL suggest we are very clear on that and Jorge is an agent that has helped us to improve the squad, just like some other agencies have.

In the midst of this unusual arrangement, Thelwell increasingly became a contentious figure at Molineux Stadium, a discourse that some Red Bull fans observed upon observing social media reaction to Thelwell’s exit:

This guy seems well-liked at his former club https://t.co/ltpuP9W2Xe — energy drink (only) soccer liker (@hcsvd) February 3, 2020

As of yet little is publicly known about how and why Thelwell was approached and signed by Red Bull. There appears to be no direct professional overlap between Thelwell and Paul Mitchell, the Englishman who has recently become a central figure in the Red Bull technical leadership under Ralf Rangnick. But if Thelwell’s sporadic encounters with the American game are any indication, it’s an assignment he sees as a fascinating opportunity. Thelwell has left a comfortable and influential position at one of the up-and-coming clubs of European football, so the power and resources put on offer by Red Bull to come across the Atlantic must have been plentiful.

Thelwell has had a front row seat to multiple quick and unlikely rises in his two decade career of soccer administration. As Red Bull New York moves forward into its first major administrative change in five years after the team’s worst season in over a decade, there can be no doubt that the man entrusted with the future knows just how much and how quickly things can improve.