Will try and do two lists and avoid crossover although ultimately some of the more current crop, one in particular, will likely end up in the top 5 of all time.
This is going to be very difficult because we've had a lot of iconic players of the years, people that really epitomise this football club and it's going to be so hard to pick just 5. But I'll try.
#1: Sir Bill Nicholson
Whilst this is about players and his biggest successes came as manager, there can be no list of Tottenham Hotspur without Mr Tottenham Hotspur himself. He spent 36 years at the club overall and is without doubt the greatest manager in our history. He played for us between 1938-1955 although of course the war prevented him from regular appearances for a number of years. However he went on to make over 300 appearances for the club and notoriously put us ahead of his England career. He was part of our 1950-51 famous push and run title winning side, the first in our history, and was a stalwart at the back.
Following his football career he went on to manage us for 16 years, winning the first double in the 21st century in 1961. Under Sir Bill we became the first club to win a European trophy, winning the cup winners cup in 1963. Bill also oversaw our Uefa Cup win over Wolves in 1972. On top of this another two FA Cups and two League cups. Wherever you look at the club Bill stamped his mark upon it, trophies in the cabinet, famous images and nights, quotes and whatever more. He's a figure that doesn't always get the recognition from the wider football community that he possibly deserves, but without doubt the greatest clubman we've ever seen.
#2: Jimmy Greaves
Jimmy is the undisputed number two on the list and the greatest goalscorer in English history. He scored 266 goals in 380 games for the club and is currently still the record holder for league goals in his career with 366.
He was signed by Bill Nicholson for £99,999 from AC Milan to avoid him becoming the first £100,000 player in 1961, and his signing was critical for our best ever side.His goalscoring record for both Tottenham and England is phenomenal and his strike partnerships with Bobby Smith and more latterly Alan Gilzean was as good as it gets for the club.
I could write more about Greaves but honestly his record speaks for itself.
#3: Dave Mackay
After Nicholson and Greaves it becomes very much a subjective choice – with a number of players easily being able to fill this slot. I’m going to go with the heartbeat of the double winning side and a custodian of the team for 9 years from 1959-1968, Dave Mackay. Mackay is probably best known for that photo of him with Billy Bremner at Leeds. However beyond that he is was one of the most successful and most influential players in our history.
With Dave leading the team we won the league, three FA cups and a European Cup. Unfortunately he had two leg breaks during his spell at the club, which is why he only made 260 odd league appearances. However it must be noted that the couple of years he spent out of the side were the years of Nicholson’s reign that we didn’t win anything. I hope that explains the sort of influence he had on the side. Whilst he was recognised and respected as being a hardman, he was also far more than that, a complete player, scoring 43 goals for us. He is very fondly remembered north of the border at Hearts as well as at Tottenham and later Derby County, where he took over from a certain Brian Clough, and won the title.
#4: Danny Blanchflower
Danny Blanchflower. I could write for hours about his importance to this football club. He could easily be number three and certainly as a player you can make the case for him being number two. The easiest way to go into Blanchflower’s influence is to repeat the quote that every Tottenham fan knows.
He said 'The great fallacy is that the game is first and last about winning. It is nothing of the kind. The game is about glory, it is about doing things in style and with a flourish, about going out and beating the other lot, not waiting for them to die of boredom.'
That is the spirit that this club has adopted throughout our history. We’ve had some absolute awful sides, and we of course have not been as successful as we should be, but we have always had stars, we’ve tried to play football in an attractive manner, and Blanchflower understood that.
Danny made 384 appearances for the club in his ten years between 1954-1964. He was the captain of the aforementioned 1960/61 side and without a shadow of a doubt the greatest Northern Irish footballer not name George Best in history. Whilst at the club he won Footballer of the year twice. Blanchflower led the side in our most successful period in our history and whilst that has been the theme of the top 4 I’m going to move to a different era for the final player
#5: Glenn Hoddle
Goddle. The King of White Hart Lane. The Tottenham product, through and through. The most gifted footballer to ever grace the White Hart Lane turf. Glenn Hoddle has to be in any Tottenham top 5. Hoddle signed for the club at the age of 12, but played professionally for us between 1975 and 1987. He also came back to manage us between 2001 and 2003.
Hoddle made his debut for the club as a 17 year old in 1975, but it was our relegation to the second division, the last time we were out the top flight, that really put him on the map. In our instant promotion, Hoddle lit up the Lane. He came back to Division One, and won the PFA young player of the year. He was in the team of the year 5 times in the 1980’s.
You speak to any Tottenham fan of that generation and they will talk to you about the special player he was. You look at a highlight reel of Hoddle goals and you will be in awe. His passing range was exceptional and he was the creative fulcrum of the side for a decade. He perhaps underachieved trophy wise, with two FA Cups and a Uefa Cup, but the homegrown Hoddle again epitomises everything sexy about Tottenham sides of old.
When he became manager in 2001, one of the biggest problems he had was still being more talented than the players in our squad. He became frustrated that they were not able to replicate what he was doing on the training pitch. If that isn’t testament to the incredible gifts he had I don’t know what is.
I have to give some honourable mentions. I could have put about 5 or 6 of players in this list.
In no particular order:
Cliff Jones: The original Welsh Wizard. Spent 10 years at the club in the 1950’s and 1960’s and still there on matchdays now. Considered to be the entertainer in the double winning side.
Steve Perryman: 861 appearances for the club. A number I don’t think will ever be beaten. My reliable
Ossie Ardiles: Probably most famous for the cup final song Ossie’s going to Wembley and his compatriot Ricky Villa, but Ossie was a special player and a huge part of our history. Ossie spent ten years (give or take the Falklands War) entertaining the crowd at White Hart Lane, and his signing after the World Cup was a huge coup for the club and the country.
Paul Gascoigne: Thankfully I don’t need to say much about Gazza. Single handedly carried us to the FA Cup in 1991. One of the most gifted English players ever and probably had the best spell of his career at Tottenham.
Gareth Bale: As above don’t need to say much. Superstar – carried us for two seasons. Second best I’ve ever seen play for the club (Hi Harry <3)
Pat Jennings: Played 673 times for the club and the best goalkeeper in our history. So beloved that we ridiculously let him go, he went to Arsenal, and he’s still unanimously loved. Thankfully he’s Spurs through and through and another always there on matchdays.
Will do the modern list at another point if there is any interest in me doing so. But if this is boring and too long read then I apologise.