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In 1990, the year Liverpool last won the league, the club's current owner John W Henry also lifted silverware.
The West Palm Beach Tropics, a team of veteran baseball players he had brought together, topped their Florida seniors' league.
That same summer, Anfield boss Jurgen Klopp signed for German second-tier club Mainz as a 22-year-old striker. Meanwhile, midfielder and skipper Jordan Henderson was born at a maternity ward in Sunderland.
With six games to go, the pressure built up over 29 title-less years will be weighing heavily on Liverpool's figureheads.
But the burden of the barren spell has been borne most by those with longer ties and lower profiles than the owner, manager or captain.
Between 1972-73 and 1989-90, the Reds had won 11 out of 18 league championships, a period of overwhelming dominance that also brought four European Cups, two Uefa Cups, three FA Cups and four successive League Cups.
Those who have followed, worked for and reported on the club for decades explain what would it mean for the wait to end...
Sephton outside the Shankly Gates at Anfield
Known as the 'Voice of Anfield', a 25-year-old George Sephton was first heard over the Anfield tannoy on 14 August 1971, making his debut on the same day as Kevin Keegan. That initial trial period has now stretched to almost 48 years. He turned 73 earlier this year.
"The word 'obsession' is right.
"It just feels wrong there are whole generations of Liverpool fans who weren't born the last time we won the league. That is just plain wrong.
"Phil Easton, who used to work as pitchside announcer alongside me, died 10 years ago. The former chairman John Smith passed away in 1995.
"If you had told them when Alan Hansen lifted the trophy in 1990 that we would not win it again in their lifetime, they would have looked at you like you were crazy.
Sephton pitchside after a Champions League tie in 2014
"Winning the title had got to be routine in my first 20 years in this job. I remember coming home in August 1984 and telling my wife that the place was as quiet as a cathedral. People were turning up just knowing that we were going to win silverware at the end of the season.
"It is like The Mousetrap [the West End whodunnit, that has been running for a record 66 years]. When you have seen it umpteen times, maybe the excitement has gone out of it a bit.
"Now, I will be happy if we win it just once more in my lifetime. I really will, that is my big ambition.
"I try not to think about the possibility of winning it. I will have to move a camp bed into Anfield if we do, because I won't be going home after the last game.
"The parties will be going on quite some time."
Tremarco outside The Arkles
Paul Tremarco has run The Arkles pub, which is 200 yards from Anfield, for the past 10 years. A Liverpool season ticket holder for the past 45 years, it is the same job he did between 1990 and 1993.
"I work downstairs and live upstairs. Every morning, I open my curtains and there is Anfield. I am passionate about the club and this is the perfect job at my time of life.
"We may be in the last eight of the Champions League, but everyone wants the Premier League, without a doubt. You can hear it in the conversations.
"When I was a young lad in my early 20s it was a matter of who came second to us. I was fortunate to live through that period and we really didn't appreciate it as we should have done.
"Now it is different and it is all about money.
Fans gather outside The Arkles before last season's Champions League quarter-final against Manchester City
"When Bill Shankly won the league in 1964, two years after promotion from the second division, that was a mega achievement. Winning the European Cup for the first time, in 1977, was massive.
"Winning the Premier League this season would be as good as that, if not better.
"I can tell you straight right now, if we do you would not be able to get in my pub from nine in the morning of that final game against Wolves.
"There would be 54,000 in the ground to see the game and 200,000 in the area just to experience the feeling of it.
"We are the outsiders, the ones no-one wants to win. Even Manchester United fans would prefer for City to win the league. Maybe it is because of our history.
"For me though, Manchester and Liverpool are rivals in football, but not as cities. We are proud of Manchester being on our doorstep and we are very similar cities in some ways.
"They have the same sayings, similar ways, even support a team in red!"
Herstad and his partner have had two children since moving to Liverpool two years ago
'We're not English, we are Scouse' reads a banner on the Kop. With a reported 580 million supporters around the world, Liverpool's fanbase is almost as cosmopolitan as the team. Tage Herstad, 45, moved to the city from Norway in 2002 to follow the team. He is the co-owner of Hotel TIA, a Liverpool-themed hotel on Anfield Road.
"I come from Floro, the western-most city of Norway. It is very nice, but they don't have Liverpool Football Club!
"One of the reasons I never get homesick is every matchday there are friends over from Norway. Liverpool is massive in Norway. It helps.
"There are thousands of people already coming over for the final match of the season, just in case. They don't have tickets, they are just going to pubs to watch it and be part of the atmosphere and party if we win it.
"I have told them to ignore the two hours that they are not in Anfield, because only 54,000 can be, and they could sell 540,000 for that match.
The bar at Hotel Tia is built over one of the safety barriers from the old Kop, while an old turnstile from the main stand has been repurposed into a table
"People are happy in the city, but very tense. You can feel it in the stadium because it is so close - one defeat, one draw and we could lose it all.
"When it first hit me was when City lost to Newcastle 2-1. I just felt sick. For the first time I realised this might happen, and it hit me in the stomach hard.
"I try not to think about previous title challenges, it burns your head out otherwise. But now we are in it again. You dream about it, you wake up early thinking about it, every match is like a cup final.
"I don't know if we can cope if we actually go on to win the league. How many jobs are going to go? How many marriages are going to go? Can we handle it?
"I am trying to be firm with myself and have to admit City are probably the best team.
"But Leicester won it one year, Manchester United won it many times when they weren't the best team, as well as many times when they were the best. We can do it. There is massive hope and I still believe. A little bit.
"If we do, after 29 years, it's going to explode. So much frustration is going to come out of Liverpool.
"If not, there will still be loads of people over, the hotel will still be full anyway, celebrating.
"In 2014, we came up short, but we still had a great time because we played good football and you just want to have a party anyway."
Lawson with former Liverpool striker Robbie Fowler
Toxteth resident Les Lawson has been to every Liverpool home game since the start of the 1976-77 season and is the chairman of the Merseyside branch of the official Liverpool supporters' club.
"It's been that long since we won the league that it's the one trophy all Liverpool fans want to win. For the generations who haven't seen Liverpool win the league it would be an amazing experience.
"It is a priority, but we are battling against a magnificent Manchester City team so it's going to be difficult.
"Winning the league became so regular for Liverpool that it wasn't really appreciated the way it should have been.
"We took it for granted. If we didn't win it one season we would win it the next.
"I can remember fans having discussions at the start of one season about how they would prefer to concentrate on the FA Cup, rather than the league, as we hadn't won it since 1974.
"We have gone close a couple of times recently. In 2009, I think back to Manchester United being 2-0 down to Spurs at half-time with six games remaining and then referee Howard Webb giving United a dodgy penalty. They fought back to win 5-2.
"In 2014, I think if Brendan Rodgers had his time again, he would have played the home game against Chelsea differently and tried to take a point. [Instead, Chelsea's counter-attack tactic earned them a 2-0 win that allowed eventual champions Manchester City back into the title race].
"It wasn't a nice experience after the Chelsea game, but to really enjoy victory you have to experience defeat. It's not a mental thing that has kept us from winning the league, it's just so hard."
"If we win the title it will be like nothing you have ever seen before," says Andy Heaton
Andy Heaton is one of the founders of the award-winning The Anfield Wrap podcast, which started as a single weekly pod in 2011 and now connects with thousands of fans through multiple weekly shows, videos and website stories.
"I'd had a season ticket on the Kop with my dad since 1988. I was 11 the last time Liverpool won the league.
"Not much was made of it, it happened every year. It is sunny in the summer, it is cold in the winter and Liverpool win the league in May, sometimes April. That is just the way it was.
"This title challenge feels different to what has come since then.
"In 2014, we came into contention very late, on the back of a good run. This year we have been in the mix from the start, so it is a different kind of pressure, and a different kind of team.
"We have the best defence in the league, Virgil van Dijk on a long contract, one of the best five goalkeepers in Europe and a well-balanced front three tied down to long contracts.
"It is not built on sand as it was under Brendan Rodgers. There is more foundation to this one.
"If City win every game they have left, they are going to win the league with 98 points and hats off to them.
"If that happens, we can look in the summer, and take the long view, be a bit more philosophical about it. But right now, this title race is all I can think about and I am nervous, nervous as hell.
"We could be 5-0 up and 10 points clear on the last day, but until I see the Premier League trophy being lifted I am not going to believe it.
"Everyone likes to think their own team is special and I accept that, but I just think if we win the title it will be like nothing you have ever seen before in your entire life."
