Liverpool won two lucky Champions League titles by overcoming 3 goal deficits against Olympiakos, AC Milan and Barcelona. In the 2004-2005 season, they had to beat Olympiakos by 2 goals in the final group stage match in order to progress. It was just Olympiakos, but Rivaldo was in that side. They fell behind by 1 goal and had to claw back 3 goals in order to win, which they eventually did. And there was that final in Istanbul where … you know what happened.
There was also that other crazy night at Anfield, where Barcelona played the second leg of the semi-final. Barcelona took a somewhat lucky 3-0 lead to Anfield, and got outplayed, although the Liverpool keeper made a few pretty good saves to allow Liverpool to race 3-0 ahead. And they did all this without Mane or Salah on the field. And towards the end of the second half, there was that iconic Trent Alexander Arnold corner.
And yet their luck in the English Premier League seemed to desert them. They last won the top flight league in 1990, 2 years before the formation of the Premier League, and they hadn't won any EPL titles. The first one they challenged for was 96-97, when they had Fowler, McManaman and Collymore. But they had a soft underbelly, and this was underscored by their nickname, “the spice boys”. They won a trio of cups in 2001, and finished second in 2002, and appeared to be on the ascendency, but they blew it in the infamous summer transfer window when they bought Diouf, Diao and Cheyrou. There was another good team, which had Mascherano, Torres, Gerrard and Alonso, and they raced Man U all the way to the end of the 08-09 season, but they came short, and that team was quickly dismantled afterwards. Then there was that 13-14 season when they raced Man City all the way, with Luis Suarez, Gerrard, Daniel Sturridge and Raheem Sterling. But they came up short in the last few games, including those infamous games against Chelsea and Crystal Palace.
But all those misadventures were with a team that was good enough to win the title, without clearly being the best. Liverpool were also unlucky not to have won 2 premier league titles by now. Last year they somehow managed to get 97 points in the league without winning, and this year, when they were the clear leaders, and a win or two away from the title, the premier league looks to end early, and even if they win a title, it will be without playing a full season.
But if you want to go back even further, you'd have to look at the two big stadium disasters that probably helped to end their status as England's greatest team. First was the Heysel disaster, in which their fans played a part. It would be hard to know how the match would have ended if the disaster didn't happen. What happened was that the collapse of the stand took place a few minutes before the game was to start, and they decided to play on anyway, because the police were afraid of what might happen if the match was abandoned. I think many of the players on the pitch were not able to concentrate on that match. It was the European Cup final against Juventus, and they lost.
The other disaster was the Hillborough stadium disaster. There was the disaster itself, in which poor crowd management caused a stampede and 95 people died, and there was the bad press afterwards, which wrongly blamed the Liverpool fans for the disaster. It was an FA cup semi-final, and Liverpool ended up winning the competition. But it's also conceivable that the stadium disaster cost them a league after Arsenal won the last match by 2 goals to win the league, in one of the most dramatic finales of a league season. Kenny Dalglish, who was Liverpool's manager, said later that the strain of going to all the funerals was a factor in him walking away from the job. His next two successors, Graeme Souness and Roy Evans, were not up to running a top club side and Manchester United ended up, in Alex Ferguson's words, “knocking Liverpool off their fucking perch”.
There's always an element of luck in football, and Manchester United's treble in 1999 was a famous example of this. There were moments when they could have been kicked out of the FA cup, or the Champion's League. And incredibly Liverpool's champion's league win was not even the luckiest. That honour would have to go to Chelsea, although they were somewhat unlucky in the manner they were knocked out in quite a few of the previous years.
Luck has played some role in Liverpool football club over the last few decades, but you have to distinguish the scale of the strokes of luck. Hiring Bill Shankly, Alex Ferguson and Jurgen Klopp are strokes of luck, although you have to wonder why Man U didn't manage to hire either Klopp or Guardiola. The stadium disasters were massive strokes of bad luck. Falling off the top around the same time that the premier league was taking off is also another stroke of bad luck, as is peaking around the same time that the incredible Man City team of 2018 was peaking. The pandemic was real bad luck, but you have to wonder what's the main effect of this, since you don't really know how the teams will change the next time the pandemic lifts enough for the league to carry on.