Ricky Van Wolfswinkel transfer to Norwich in 13/14. Ricky scored on his Premier League debut, and never scored again. Norwich finished the season with just 28 goals, and got relegated. As you can imagine, relegation is a huge financial impact, and it meant Norwich had to cut their losses by selling their two best players in Robert Snodgrass and Leroy Fer.
John Hartson - The acquisition of John Hartson to Wimbledon, made him a club record signing at £7.5 million. Scored two goals in his first premier league Season. And in his second season, he fared better on the goal scoring front, but much to the dismay of Wimbledon, missed out on pretty much the whole second half of the season, was something like December till May he was out.
This was especially unfortunate as it meant he was unavailable to play in their shock defeat in the Fa Cup to Fulham who although decent in 2024, but at the time of 1999/2000 it was the case that Fulham were playing in the first division, so could have been a real opportunity for Wimbledon to cash in on the financial opportunities, such as the prize money for each round, especially given that the very Fulham that knocked out Wimbledon, went out to Tranmere Rovers who were also languishing in the First Division. I don't say that to knock Fulham or Tranmere, its just that expenses can quickly add up and need to be covered by revenue streams such as ticket sales, increased gate receipts, broadcasting rights (matches in the latter stages are often televised and just imagine if it was a home game which presents opportunities for merchandise to be sold etc) , sponsorships, and prize money from competitions like the FA Cup.
Unfortunately, with his injury woes it was difficult to move him on, meaning John Hartson had to leave on a free transfer. And remember how I mentioned he was out for the majority of the second half of his second season, well there were significant implications in the league. As I mentioned earlier, he fared better on the goal scoring front in his second season as Wimbledon had a decent start to the campaign in 99/00 with some crucial draws. It was his absence for the second half of the season which contributed heavily to Wimbledon's results falling off a cliff, and they ended up being relegated. To put that into perspective, since the Premier League was formed in 1992, they hadn't been relegated once. And Wimbledon never recovered, they were dissolved in 2004.
José Bosingwa - QPR - Bosingwa joined QPR in 12/13 on a three year contract. And he was horrendous, to the extent he was their worst player in 12/13. To make matters worse, it wasn't just on the pitch he caused issues, at one point he refused to be on the bench. Needless to say, QPR were relegated and ended the players contract after a nightmare debut season, and took their losses on the two years left on his contract. Disastrous.
Fun fact, this reminds me of a special case. Well fun for me at least. If this isn't palatable to what you expected from creating the thread
@Fortitude then by all means let me know. Naturally in a thread title predicated on worst signings in Premier League history, I normally wouldn't mention this signing, but I feel given the mitigating circumstances it at the very least contributes to the conversation. Basically
Jean-Kévin Augustin's stint at Leeds United in January 2020 is a prime example. It's worth noting that Leeds were in the Championship at the time. Leeds had the option to sign him permanently for a hefty £17.7 million, but things didn't quite go as planned.
Augustin's time at Leeds was plagued by injuries and rumors of him not following the coach's orders. What makes this story stand out is that Leeds actually secured promotion to the Premier League that season, and its been reported that there was a clause in the contract that made Leeds obligated to complete a permanent transfer as a result of a promotion clause.
So this should've been a signing for Leeds in the Premier League. However, Leeds used the unique situation of the Corona Virus to insist the clause should be voided, and obviously RB Leipzig were having none of it. So Leeds made their appeal, and lost. They actually made a second appeal which was withdrawn in 2024 from the Court of Arbitration for Sport. Speaking of bang for buck, this is a player that had just 48 minutes in the Championship and zero minutes in the Premier League. And this would be quite the financial setback.