Exclusive:I was behind Simon Jordan's look at buying Sheffield Wednesday - we'd have done a Wrexham-style documentary
Social media was lit ablaze last week when former Crystal Palace owner Simon Jordan revealed his involvement in a group that took a look at buying Sheffield Wednesday. Here, Alex Miller talks to the Sheffield-born entrepreneur he had teamed-up with.
“When I got to reading a bit about Sheffield Wednesday I picked up the phone and spoke to Simon,” says Ryan Howsam, the insurance entrepreneur who has been close friends with former Crystal Palace owner Simon Jordan for over two decades. “Given I'm from Sheffield, knowing a bit about Wednesday and its history, I thought it would be a really good opportunity to really build out in a different way. I asked Simon's opinion and he was interested, so we decided to take a look at it.”
The 59-year-old speaks to The Star from his base in Dubai and does so with an enthusiasm for the subject matter. Last week during one of his regular stints as a broadcaster for national radio station Talksport, Jordan publicly revealed that he had been part of a consortium that had provided administrators with the £50m proof of funds required to enter the second stage of the process to buy the club out of administration. He didn’t name Howsam specifically, but the clues were none-too-subtle.
Proof of funds had been shown and amid a long and detailed look at the information offered to those who had done so, a meeting had been held with one of the administrators by one of the two other people who were assisting in the group.
But it’s made clear early in the conversation that the Howsam-Jordan bid didn’t materialise into a formal offer after it became plain the cost to buy the club would surpass the figure they had in mind. Though he winced at the use of the term, Jordan had suggested he had thought the club to be ‘nickable’ given the circumstances and subsequent investment required to turn its fortunes around. He has long since spoken of Wednesday as the EFL’s foremost prospect in terms of an investment opportunity for the right owner.
Jordan publicly baulked at the prospect of ‘rewarding’ Dejphon Chansiri with the payment of around £15m needed to satisfy the EFL rule that requires clubs to pay secured creditors 25 pence in the pound to avoid a points deduction next season. Howsam speaks on similar themes - and suggests it was that figure that took the asking price to a level that wouldn’t have been in-line with their strategy for the club. Administrators have confirmed that other bidders have placed offers exceeding the £30m required to clear the threshold to avoid that 15-point deduction threat.
“We were thinking of a lower bid than has been touted,” he explained. “When you put the money owed to Chansiri together with some of the secured creditors, there's the money that needs to be spent on the stadium. We did try to speak to the holders of the stadium (to see if a deal could be struck) but they wouldn't speak with us.
“With all the football creditors, you're at the £30m mark to buy the club, then it's about what it would cost to get it to a level playing field. Ultimately you've got to get it to the Premier League to make any money and in a heartbeat you could go through another £100m. So it was a tough one, but we pulled back.
“We had a good look at the financials and we thought it might be gettable at an attractive price. I thought if we could get the club for perhaps a discount of what it was worth and then put that money into rebuilding it, that would feel like a good investment.
“At that point we didn't know the strength of the bids that would be going in, but had we put in a lower bid and got it, the starting point may have meant the club starts the following year with a 15-point deduction. That wouldn't have gone down well with the fans and I think you're setting yourselves up for quite a difficult start; the fact is that something goes wrong, you end up going down another division. It just felt too risky at that point.”
The life of Ryan is an interesting one. Born into council accommodation into a modest upbringing, he started out selling double glazing and alarm systems in his mid-teens. He moved into entrepreneurship in his early 20s and was subject to the highs and lows of life in business before making his way in insurance with the foundation of multi-brand group Staysure in 2004. Since 2018 he has run a capital investment group and two years later moved to take a majority equity share in the Legends Tour, a world-renowned golf tour that showcases some of the most notable senior names in the sport and whose prize pool in 2025 topped €20m.
The tour’s commercial strategy is overseen by Howsam and it is with that experience of sport as business that in different circumstances he feels he could have gone about the management of Wednesday in a different way to most clubs. Alongside Jordan, an entrepreneur in his own right, he feels their combination of shared business experience and his partner’s experience of football could have made an intriguing combination - both in terms of the management of the club and in a wider commercial sense.
“When you're looking at any business you've got to think of ways to build the brand out to a global audience,” Howsam continued. “United have managed to do that on the back of being in the Premier League and one or two other things. At Wednesday I felt you could build something around what's already there, with the unique name and the Owls iconography and so on.
“Obviously you've got to get it right on the field and you've got to know what you're doing to build a team, but there were other areas of interest. There's women’s football that can be built out and I think that could be a real opportunity, and then there's the whole youth programme. You've got to create something that is sustainable and that's something that's very, very difficult in football, particularly in the Championship. It's difficult to get it right.
“With the Legends Tour, we've built out an ecosystem of products and services that are made for that mature audience in golf. There's a similar opportunity for this brand to do something off the football pitch. Simon's following is also quite substantial, so we felt there would be quite a lot of interest in the narrative of the two of us together. We felt it would get an immediate set of eyeballs in the media.”
Though a passionate Sheffield-born sport fanatic, Howsam admits he has always been something of an ‘agnostic’ when it comes to supporting either Wednesday or United. Though their exit from the process meant commercial ideas had not been fully fleshed-out, he mentions a new apparel brand being part of the potential business strategy and as a viewer of behind-the-scenes football docuseries such as Welcome to Wrexham and Built In Birmingham: Brady & the Blues, feels those media eyeballs could have been put to good use with a similar project at Sheffield Wednesday.
“I think something like that could have happened with Wednesday, especially with Simon involved,” he said. “It's that type of thing I was thinking about. Look, every business guy thinks they can achieve things in different industries and that can also be a recipe for disaster, but I have done things with a sporting franchise albeit with golf.
“I've watched the Wrexham stuff but particularly with the Tom Brady thing at Birmingham, he's such an impressive character. The way that his mind works, you need that type of mindset at that club somebody who is relentlessly positive about what you can do and where you can go. That's what I try to bring to my businesses and with Simon would have brought it to Sheffield Wednesday.
“The golf for me has been a passion project and we've made a success of it, but coming from Sheffield, being passionate about Sheffield, we could have had a lot of fun with it. But you've got to have the solid starting point and it has to make commercial sense. The numbers have got to be right.”
So it won’t be them. Suitors are being whittled-down to a manageable number and the understanding is that Wednesday’s administrators hope to be able to move towards a preferred bidder status in the next week or two, with a view to the takeover process being complete sometime around the new year. Having taken a long look at the numbers made available to those who offered proof of funds, there’s a confidence on Howsam’s part that there are no terrifying skeletons in the closet financially - and with an insight into some of the parties that remain interested in doing a deal, there’s a hope of a suitable new owner at Hillsborough.
“We did quite a lot of financial due diligence and it's all laid out,” he said. “Once they get to the stage of naming a preferred bidder, they’re really going to dig into the financials but at the level we were operating at, we didn't see anything (of concern) beyond the stadium costs. They (the administrators) seem to be very transparent and are running it in an orderly fashion.
“From what I understand there are quite a few other well-heeled players in there. There are people with substantial wealth and hopefully the club will end up with the right owner. I think we would have thought about it in a different way to the rest. Simon's following, the fact I'm from Sheffield and care about the city and community, it would have been a really good journey. But unfortunately it just didn't stack up in the numbers.”