A family business now in its’ third generation of ownership, Jenningsbet is one of the largest independent bookmakers in the industry, employing more than 500 people across its fleet of retail shops.
The man who started it all though, was Joe Jennings, an ex-jockey turned bookmaker with a small stature but a big personality.
He can’t have known that his little bookie business would turn into a family enterprise that still supports his children and grand children even today, but Jenningsbet certainly does that, with practically every member of the family working for the company or its’ sister company, Joe Jennings Bookmakers, in one way or another.
They resisted several take over offers in their earlier days, preferring to keep the business in the family, and that is a decision that later generations have no doubt been thankful for, and even with Joe Jennings himself having long since departed, there seems no desire to sell up.
The company has something of an odd structure, with two very similarly named companies operating separately while both being run by members of the same family, and in some cases some of the very same people, but it clearly works for them.
How Joe Jennings Became a Bookmaker
From Joe Jennings Bookmaker
Joe Jennings was born in 1944 towards the end of WW2, in the Essex area.
As a younger man, he became interested in horse racing, and since he was small, went into training as a jockey under Ted Smyth in Epsom.
His riding career wasn’t long or illustrious, although he did bag a couple of wins, but his real claim to fame which he loved to tell people about at parties, was that he was once involved in a photo finish for the Wokingham Handicap, ultimately losing out to none other than Lester Piggott.
His racing days ended around 1959, and when the gambling law changed in 1961 to allow off track betting for the first time, Joe Jennings went into business with his father, Tom, and together they opened their first betting shop.
The name was not Jenningsbet at this point, but Harlow Pools Ltd, and you get no points for guessing where it was located.
Interestingly, theirs was the first ever high street bookmaker in the area, and the company still run that shop today.
The business went from strength to strength during the following few decades, growing to 32 shops in Essex and the Home Counties by the early 1990s, and also rebranding to Jennins Bookmakers along the way.
Joe had also enlisted the help of his brother, Terry and his sister, Carol, so the Jennings Bookmakers high street shops really were a family business.
Retail outlets were not their only source of income though.
Joe Jennings had been smart enough to begin offering telephone betting from 1970 onwards, a service they still provide today, and this helped the company reach customers who were perhaps not local to one of the Jennings’ shops.
It wasn’t just the business that had been growing either.
Joe Jennings had 5 children by 1995, and his extended family was large too as his siblings also had children of their own.
This created a whole new generation of Jennings, many of whom would go on to work for the business.
Joe Jennings Bookmaker Splits into Three
In 1995, Joe Jennings took the decision to split the company three ways, but still keeping every part of it in the family.
He would retain the Joe Jennings Bookmakers brand, while his nephews Greg and Julian Knight (sons of his sister, Carole) would establish Jennings Racing, which would go on to become Jenningsbet.
Terry Jennings, Joe’s brother, would also take a few betting shops for himself.
The split was not because of any sort of falling out, so everything was perfectly amicable, and the businesses would often help each other out when necessary.
Terry Jennings side of the business would eventually re-merge with Jenningsbet, but the other two Jennings brands continue to this day.
Interestingly, the two brands are sometimes described as being part of The Jennings Group, although no official such company exists.
It could be that this is just an informal way that those in charge refer to themselves, since despite being two legally different businesses, they are still very closely related.
Joe Jennings Bookmakers
Joe Jennings Bookmakers maintains its’ independence, and you could call it a niche sort of bookmaker.
They kept their portfolio of betting shops numbering just 15, resisting the temptation to expand further, and although this modest chain includes the original shop in Harlow and one or two others in that area, the rest are all either on the Isle of Man or on Jersey.
That in itself is an interesting approach to the business, but they have also held firm with telephone betting in all its forms where other much bigger brands have knocked this option on the head.
This all gives Joe Jennings Bookmakers something of an antiquated traditional feel, which is why a lot of their customers like them, but they are by no means a firm that is stuck in the past.
They opened their first website in 2004, and although it was more of an advertising page than anything else (you couldn’t place bets on it at that point) once Jenningsbet opened their online sportsbook in 2006, Joe Jennings Bookmakers linked through to them for this purpose.
Building on their telephone betting service, in 2012 they took their first bet via text, and in 2018 Whatsapp betting facilities became available, moving on to the Telegram app for better security after Whatsapp changed their privacy policy.
They offer their own sportsbook platform these days though, although unbelievably, it only opened in 2022; before then, they only took bets in store and over the phone.
So while Joe Jennings Bookmakers has remained in the background, and some might say in the shadow of Jenningsbet, it was never trying to do anything different.
Joe Jennings Bookmakers still proudly call themselves one of the UK’s oldest independent family bookmaking businesses, and they really mean it. Joe Jennings’ grandsons, Jason and Harry, both work as traders for the company and have been involved since they were old enough to work there.
Joe Jennings himself very suddenly and sadly died in 2002, aged just 58. He was on holiday on the island of Tobago when he passed away peacefully in his sleep.
His son, Jason Jennings took over the business shortly after this, stepping down in 2013, when none other than Greg and Julian Knight took the reins.
Jenningsbet (Jennings Racing)
In contrast to Joe Jennings Bookmakers, Jennings Racing went on a bit of a crazy growth journey, opening and acquiring new betting shops like there was no tomorrow.
The two Knight brothers, along with the help of their mother, built the chain of 32 shops in their local area, to a huge portfolio of around 150 stores nationwide today.
Although Jenningsbet (which still operates under the Jennings Racing moniker officially, although they rebranded in 2002 after Joe’s death) is the more visible of the two Jennings brands, they stuck to the South of the country until 2013, when they opened their first shop up North, in Manchester, starting a decade long expansion mission.
This, incidentally, is also when they became directors of Joe Jennings Bookmakers, so clearly some sort of company restructure took place at this point, and The Jennings Group began to think bigger, with Jenningsbet leading the charge.
After Manchester they opened shops in Leeds, Sheffield, Newcastle, even Grimsby got one as the Jenningsbet brand spread slowly but surely towards Scotland, although they never crossed the border.
Their online sportsbook was operational by 2006, however, they did not run their own platform but used first FSB tech, and then Altenar, before oddly closing down their online operation between 2022 and 2023.
This coincides with Joe Jennings Bookmakers launching a sportsbook for the first time in their history, so once again it seems as though some sort of company reshuffle was going on – perhaps they decided that Joe Jennings Bookmakers would become the remote betting side of the business, while Jenningsbet focusses fully on high street betting.
The move also came shortly after Julian Knight stepped down from Jenningsbet and Joe Jennings Bookmakers, leaving Greg Knight to run things on his own, which would make sense of big changes occurring shortly afterwards.
Whatever the reasons, both brands still run solid businesses today, and the ancestors of Joe Jennings are doing very well from the company he started back in 1961.