#3 Paul Konchesky (2010)
This was an utter and complete disaster of a transfer in every way possible. Another one of Roy's classics, brought in by the current Crystal Palace manager. Paul Konchesky had played under Hodgson at Fulham and joined him at Anfield for a baffling fee of around £5 million. He came in and replaced promising left-back Emiliano Insua, who was loaned and eventually sold. This was a transfer that made no sense whatsoever, even Hodgson himself could not justify it.
Konchesky is the face of the absolutely horrendous time on the pitch that Liverpool fans had to suffer through. He is the worst of a very bad bunch and had no right to be playing as a home player at Anfield. He kept on putting in worse and worse performances. He was so bad that Liverpool fans started cheering when the left-back was substituted in a 1-0 home defeat to Wolves. Yes, Liverpool lost to Wolves at Anfield in the Premier League. That's how bad it got.
When Kenny Dalglish returned to Liverpool, much like Poulsen, Cole and even other bad signing Milan Jovanovic, Konchesky hardly got a look in as things became better. It was no surprise that Liverpool improved under the King and without most of their poor summer signings of 2010. But perhaps the lasting memory of Konchesky's time at Liverpool is when his mother Carol Konchesky vented her anger on Liverpool fans who were rightfully critical of left-backs performances at Anfield by posting a rant on Facebook. Some legacy, indeed.
#2 Mario Balotelli (2014)
2013-14 was an excellent season for Liverpool. They were inches away from winning the Premier League title and Luis Suarez had won the Golden Boot and the PFA Player of the Year award. However, the aftermath of that season would be unfortunate for the Reds. Suarez ended up leaving for Barcelona as Liverpool tried to salvage some new talent for their squad. Brendan Rodgers made a bunch of signings, both hit and miss. The likes of Adam Lallana, Dejan Lovren, Emre Can and Divock Origi made their way to Merseyside. But they still needed a striking replacement for the outgoing Uruguayan. Liverpool seemingly poached Loic Remy from QPR but he failed the medical, so Rodgers decided to take a major risk for his marquee summer striker signing.
Mario Balotelli joined Liverpool from AC Milan for £16 million. Fans were understandably excited as Balotelli had shown fantastic potential at all of his previous clubs. Everybody thought that he would continue to flourish under the great man-manager Rodgers. However, it all blew up. We saw all the wrong qualities of the Italian striker during his time at Anfield. He just could not score despite all the golden opportunities he was getting. This was a time where Liverpool's strikers were famously not up to the mark, with the likes of Balotelli, Rickie Lambert, Fabio Borini and a hardly fit Daniel Sturridge.
Balotelli would end up scoring four goals for Liverpool, one in each competition. It is stunning to see just how poor he really was at Anfield, possibly the Reds' worst striker in the past fifteen years. He would return to the San Siro on loan and was told, in 2016, that he did not have a future at Liverpool by Jurgen Klopp. Balotelli went to Ligue 1 club Nice on transfer deadline day. This transfer was an unnecessary risk taken by the current Celtic boss as an answer to the ever-consistent Luis Suarez. Suarez scored 31 goals in his last season, while Balotelli got 4. Liverpool actually paid £4 million for one Mario Balotelli goal, really unbelievable.