Tottenham Chairman Daniel Levy is known for his shrewd transfer decisions, perhaps most famously Gareth Bale, who joined for €14.7 million in 2007 and left six years later for €101 million for a then-football transfer fee record, and while Daniel Levy's strict budget doesn't always win over fans, he has made Tottenham Hotspur a european powerhouse, though not every signing to Tottenham has been successful. There are also relatively bad decisions, so the question is, who are the five worst signings in the history of Tottenham Hotspur club? Let's take a look at it together.
5th place: Eld Postiga 9 million euros

After becoming a promising player at Porto, Elder Postiga moved to Tottenham Hotspur for €9 million in 2003, what should have been the next great step in his career, but by the end of the season he had been sent back to Porto by the club.
Eld Postiga was part of Glenn Hoddell's summer recruitment programme, with fellow strikers Frederick Canute, Robbie Keane and Bobby Zamora also arriving at White Hart Lane, in an effort to ease the burden on veterans Les Ferdinand and Teddy Sheringham, who unfortunately failed to make his mark in the Premier League and scored just two goals in 24 games for the team, paving the way for his return to Porto in the summer of 2004.
4th place: Vincent Janssen 22 million euros
The 25-year-old became a big name in his native Alkmaar in the Netherlands, where he made 49 appearances for the club in all competitions and scored 31 goals in 2015-16, and in the summer of 2016, Tottenham Hotspur signed him for €22 million.
But after coming to England, Vincent Janssen found that the rivalry and competition in the Premier League was completely different from that of the Dutch First Division, and in the 2016-17 season, he played 38 times and scored only 6 goals, which was obviously sorry for his value, after which the Dutchman was loaned to Fenerbahce for a season, and then sold to Monterrey Mexico for 9 million euros by Tottenham Hotspur in July 2019.
3rd place: Mbolo Mabizzella 2.3 million euros
Mbolo Mabizzella impressed Tottenham Hotspur in the 2003 Orlando Pirates pre-season friendly, so Glenn Hoddell signed him for €2.3 million, which didn't seem like a bad thing until the start of the season.
However, Mbrolo Mabizzella did not start in his first seven games for Tottenham Hotspur in 2003–04 and made only two appearances for Tottenham Hotspur before joining Vallerenga as a free agent in January 2005.
2nd place: Jonathan Blunder 2.8 million euros
Jonathan Blundle made impressive progress at the elite club of Muskron as a teenager, becoming one of the main players of the squad and helping them win the Belgian Cup, when many people said he was one of the most promising young players in European football, so in the summer of 2002 Tottenham Hotspur signed him for 2.8 million euros
But life in north London is completely different from Belgium's, the opportunity for the first team is gone, and after playing twice for Tottenham Hotspur, Jonathan Blundell was brought back to Belgium by Bruges for 1.2 million euros in January 2004, after which he played for Bruges for 11 seasons, helping the team win 1 league title and 2 Belgian Cup titles.
1st place: David Bentley 22 million euros
The former Arsenal midfielder moved from Blackburn Rovers to Tottenham Hotspur in the summer of 2008 for a staggering €22 million and after failing to break into Arsenal's first team, he was determined to play in White Hart Lane, but despite five seasons for the White Lily, he only made 62 appearances in all competitions for the team.
David Bentley got off to a good start at Tottenham Hotspur, but he fell out of favor towards the end of the 2008–09 season and did not improve over the next two seasons, which led Tottenham Hotspur to loan him to Birmingham, West Ham United and Rostov before retiring in 2013 at the age of 29.
In addition to the above 5 players, what other bad signings in the history of Tottenham Hotspur have impressed everyone? Welcome to leave a message in the comment area to add.