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In modern times, we can’t really say that the O’s are among the richest teams out there. Even back when the market wasn’t as hectic and money maybe not as scarce, and when they were breaking their own records more regularly, the fees were never really huge to begin with. On top of that, it has been decades since they last managed to splash the cash on a big signing.
Justin Channing, the player who arrived from Bristol Rovers in 1996/97 for £286,000, is still the most expensive signing in the history of the club and he hasn’t been dethroned for more than 20 years now.
Before Channing, the record-holder was actually signed all the way back in 1989/90 from Wigan Athletic as Leyton Orient forked out a sum of £225,000 to get Paul Beesley into the team. And their big signing before Beesley? Mervyn Day – a goalie from West Ham United who penned a contract for £153,000 in… 1979/80. Yup, that’s right.
Essentially, they were breaking their record every decade or so but then, at the start of the new millennium, they simply had to stop as money was tighter and transfer prices suddenly skyrocketed. When it comes to exits, however, there are still a few big names we have to mention.
Gabriel Zakuani is a fairly recent departure from the club and Leyton Orient got £1.3m from Fulham for the player back in 2006/07. To this day, that transfer is the biggest piece of business they have ever conducted, both incoming and outgoing ones included.
Zakuani is then closely followed by Moses Odubayo who switched to Brentford for £1.1m in 2014/15. After him, there is John Chiedozie and his £635,000 move to Notts County all the way in 1981/82.
We cannot be talking about famous transfers without mentioning the young full-back Odubayo and his big-money exit to Brentford. He was a brilliant servant to the badge and also quite a fan-favourite as well. Along the more recent transfers is also Macauley Bonne who definitely warrants a shout as his great stint following his arrival gave him a big transfer into the Championship as well.
Then we have the likes of Jonathan Tehoue for that heroic day against Arsenal or Channing for the incredible transfer fee the club had to fork out to get him back in the day.
We could go on with Beesley, Day or Zakuani for very much the same reasons but there could be far too many to count and someone is bound to miss out on the list.