Towards the end of his playing career, as he contemplated what he would do once the big pay cheques stopped coming in, Tim Sherwood began to dabble in business. He set up a sportswear business called Prime Teamwear which, having started out with big ideas, was sold on to Gary Childs, of Boston United. He was then involved, along with Jamie and Louise Redknapp, in setting up a magazine called Icon, targeted at footballers, their wives and those aspiring to a “luxury” lifestyle.
Predictably, Icon proved even less sustainable than the lifestyles it promoted, but not, it is said, due to any deficiencies on Sherwood’s part. By all accounts, he was hands-on, full of ideas and enthusiasm, even down to proof-reading each page. He is that type of guy; as he demonstrated in his playing days, which peaked as captain of Blackburn Rovers’ Premier League title-winning team in 1995, he is not afraid to get stuck in.
All of which suggests that, when it comes to his new role as director of football at Swindon Town, Sherwood at least has the necessary work ethic. The contacts? Certainly. The vision? One would hope so, though it is hard to imagine that he faced the most rigorous of interviews. Lee Power, the Swindon owner, had been desperate to get Sherwood on board even before he completed his takeover at the County Ground in 2013. The pair have been close friends since their time together at Norwich City in the early 1990s, encompassing their failed venture together with Icon and, yes, even Prime Teamwear, which was sold on to Childs, who happened to be a team-mate of Power’s at Boston United at the time. Maybe they are banking on Swindon being third time lucky for their double-act.

The Swindon set-up is unusual in the extreme. This is a club owned by a former top-flight player — even if you would be forgiven for not remembering Power as such — and with another as director of football, yet their head coach, Luke Williams, is a 35-year-old with scant playing pedigree. Williams played in the youth teams at Norwich and Bristol Rovers before dropping down to non-league Ashford Town, the Middlesex-based club, and was earning a good reputation through his work with Brighton and Hove Albion’s under-21 team when he was appointed to Swindon’s coaching staff on the recommendation of, you guessed it, Sherwood in 2013. Ross Embleton, Williams’s assistant, is another Sherwood protégé, having worked closely with him in two spells at Tottenham Hotspur, either side of a spell coaching at Bournemouth.
It all makes for quite a tangled web — and this before we go into Power’s relationship with Swindon’s supporters, few of whom are enamoured of his regime — and it points to a number of things. One of them is the influence a high-profile individual can have on one club from afar, even when under the employment of another. Over the course of 2012-13 and 2013-14, when Sherwood’s star was on the rise at White Hart Lane, Swindon took seven players on loan from Tottenham and signed another two on a permanent basis. There was even talk of formalising a long-term strategic partnership between the clubs. Then, when Sherwood was moved on after a spell as interim head coach, the Tottenham-Swindon relationship fizzled out.
At a media conference on Thursday, Sherwood played down the idea that he would be de facto manager at Swindon, saying how highly he rates Williams and suggesting that he was “just coming in to help out wherever I can”. Power, though, said that Sherwood “will be taking training and working alongside Luke Williams and Ross Embleton” and that he will also “head up all aspects — that will be transfers, that will be the way we play, the formations and the picking of the team”. For someone who is “just coming in to help out wherever I can”, that sounds like quite an extensive brief.
It is not yet clear whether Sherwood, after his various business partnerships with Power in the past, has taken or intends to take a financial stake in Swindon, but, either way, it looks a more appealing proposition for him than it might appear at first glance. If he has accepted that there are no top-flight job offers in the pipeline after more than a year out of work since being sacked by Aston Villa, whom he led to the FA Cup final and to survival in the Premier League from what had looked a bleak position, then he might also be right in concluding that he would be on a hiding to nothing if he took a job in the madhouse that is the Sky Bet Championship.
If he wanted job security and power, then the job at Swindon, 21st in League One, probably looked a good deal more appealing than many management positions.
That, in itself, hints at an uncomfortable truth about English football, where the cult of the manager is so powerful yet there is often — on the terraces, in the media and, where it matters most, in the boardrooms — such a dismissive attitude towards the work done behind closed doors or on the training field. So many former players like the idea of coaching, yet many of those lucky enough to land a management job are out of the door before they have got their feet under the table and plenty do not get a second chance. There is so little patience that you can understand why more and more high-profile players prefer the comfort of the television studio — less work, no stress, much more job security and, when it comes to elite players, more money.
The Sherwood case is a reminder that there could be another career path, and certainly there are a number of players or former players whom one could imagine immersing themselves in a director-of-football role or the type of general-manager position that has awaited many a distinguished retiree in Germany or the Netherlands. Gary Neville has suggested that coaching might not be for him, but he would seem to have the perfect outlook, vision and attitude for a director-of-football role. So too, perhaps, the likes of Frank Lampard and Jamie Carragher, very different personalities but united by strong views on how clubs and youth academies should be run.
Given the lack of football knowledge and vision in an increasing number of boardrooms, the position of manager or head coach looks more precarious than ever, but the converse of that effect is a growing need for strategists and planners, people capable of forming a long-term outlook that will withstand the inevitable changes in the dugout. That is why the appointment of a former England international, a title-winning captain, as director of football at a League One club seems like such an interesting development — though it would be far more refreshing and intriguing if it did not all appear far too chummy for comfort under an unpopular regime whose only successful strategy so far, in three years at Swindon, has been to phone a friend.
Qualifying groups seem unfair
A 3-0 defeat by Brazil on Thursday night has left Argentina — the team of Javier Mascherano, Sergio Agüero, Gonzalo Higuaín and, of course, Lionel Messi — in danger of missing out on the 2018 World Cup. After 11 matches in that gruelling South American qualifying section, Argentina lie sixth — and only four teams make it automatically, with the fifth facing a play-off.
Shame on them, you might say, but this is what happens when you get — according to the Fifa rankings, which in this case seem reasonable enough — five of the world’s top ten (Argentina, Brazil, Colombia, Chile and Uruguay) competing with other competitive football nations, such as Ecuador, Peru and Paraguay, for four and a half places. It is fiercely competitive, but it is brutal and it leaves strong teams at risk of missing out. There are far fewer nations in South America, of course, but, given that Europe will provide 13 teams, several of whom will qualify while barely breaking sweat, as well as the hosts, Russia, the balance seems wrong.