Amid their painful trophyless streak stretching all the way back to the 2007-08 season, Tottenham Hotspur have unsurprisingly seen several revered names depart in search of silverware down the years.
Many of those expensive sales did manage to fulfil their trophy ambitions elsewhere, and whether Spurs reinvested the money received well for each of them is firmly up for debate.
Here, Sports Mole looks at the most expensive sales in Tottenham Hotspur's distinguished history.
10. Kieran Trippier - £18.7m
To: Atletico Madrid Date: July 17, 2019 Age at the time: 28 Tottenham appearances: 114 Tottenham goals: 2
Honours at Tottenham
None
9. Robbie Keane - £20.4m
To: Liverpool Date: July 28, 2008 Age at the time: 28 Tottenham appearances: 306 Tottenham goals: 122
Honours at Tottenham
8. Christian Eriksen - £23m
To: Inter Milan Date: January 28, 2020 Age at the time: 27 Tottenham appearances: 305 Tottenham goals: 69
Honours at Tottenham
None
7. Michael Carrick - £23.1m
To: Manchester United Date: July 31, 2006 Age at the time: 25 Tottenham appearances: 75 Tottenham goals: 2
Honours at Tottenham
None
6. Steven Bergwijn - £26.6m
To: Ajax Date: July 8, 2022 Age at the time: 24 Tottenham appearances: 83 Tottenham goals: 8
Honours at Tottenham
None
5. Luka Modric - £29.8m
To: Real Madrid Date: August 27, 2012 Age at the time: 26 Tottenham appearances: 160 Tottenham goals: 17
Honours at Tottenham
None
4. Dimitar Berbatov - £32.3m
To: Manchester United Date: September 1, 2008 Age at the time: 27 Tottenham appearances: 102 Tottenham goals: 46
Honours at Tottenham
3. Kyle Walker - £44.8m
To: Manchester City Date: July 14, 2017 Age at the time: 27 Tottenham appearances: 229 Tottenham goals: 4
Honours at Tottenham
None
2. Harry Kane - £80.8m
To: Bayern Munich Date: August 12, 2023 Age at the time: 30 Tottenham appearances: 435 Tottenham goals: 280
Honours at Tottenham
None
1. Gareth Bale - £85.9m
To: Real Madrid Date: September 1, 2013 Age at the time: 24 Tottenham appearances: 237 Tottenham goals: 71