As Jordan Henderson prepares to put the final touches to his move to Ajax after ending his three-year contract with Al-Ettifaq within six months, it is hard to think if any transfer moves have turned out worse.
Upon taking the decision to leave Liverpool, Henderson made the choice to depart a club that is challenging on all fronts and looks rejuvenated this season at the top of the Premier League under Jurgen Klopp.
The 33-year-old also soiled his reputation by moving to a nation where homosexuality is illegal, with the midfielder previously a big advocate for LGBTQ+ rights during his time at Anfield.
He also endured a dismal time on the pitch at Al-Ettifaq, with Steven Gerrard's side languishing in mid table in the Saudi Pro League, while they have regularly played in front of just a few hundred fans.
Reports also broke on Wednesday that Henderson has not even received a penny of his mouth-watering £350,000-a-week wages at Al-Ettifaq, having deferred payments in the last six months, with sources claiming there is a belief that Henderson will never be paid what he is owed.
In light of Henderson's failed stint in Saudi Arabia, Mail Sport takes a look at some of the other worst transfers of all-time.
Philippe Coutinho - Liverpool to Barcelona for £105m, rising to £142m - 2017
After a stunning five-year spell at Liverpool, where Philippe Coutinho proved himself as one of the best attacking midfielders in the world, he moved to Barcelona with huge expectations.
However, the transfer was a disaster from the start as the Brazilian was continually blighted by injuries and failed to replicate his form from Anfield.
After a difficult 18 months, he moved on loan to Bayern Munich and even had a hand in knocking Barcelona out of the
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