Collingwood.
19 Grand Finals for three wins, two draws, 14 losses, across 65 years so we are talking three+ generations.
An amazing source of analysis for how the culture/psyche of a club can persist across presumably distinct groups of people occupying it, and how Grand Final day performances can so often not reflect the teams' performances throughout the season.
1958 - Finshed second three wins behind Melbourne (with the same percentage). Melbourne belted Collingwood in the Second Semi Final by 45 points. Collingwood win the big one in what was by all accounts one of the biggest upsets ever, protecting their four-in-four record from 1927-1930.
1964 - Finished second to Melbourne in a very close season (if Hassa Mann had not kicked a goal towards the end of the second last game against Hawthorn, Melbourne's top spot and Hawthorn's fifth (i.e. out of the finals then) would have been reversed). Went down to Melbourne by only four points in the Grand Final.
1966 - Top spot by a game and 14% plus (percentage often a better indicator of how dominant a team was during the season). Before my time, but aside from all the romance of the Aints winning their only flag by a point, I imagine Collingwood were raging favourites? Had beaten St Kilda in the second semi by 10 points and in their only home and away meeting by 12 goals.
1970 - Often touted as the most dominant side not to win the flag. Finished two games and 24% ahead of Carlton in second spot. Lost three of 22 home and away games (all away) by six, one and twelve points. Famously 44 points ahead at half time of the Grand Final (and still 17 up at three-quarter time).
1973 - Special mention - did not even make the Grand Final. Not as dominant but still finished two games clear on top (two of their three home and away losses were heavy). Out in straight sets, interestingly to the two teams that beat them big during the season (Carlton and Richmond). Six goals ahead of Richmond at half time in the Preliminary Final. R.Hart comes on. Game over.
1977 - Interesting. Another minor premiership but only by one game and not even the best percentage in the league but 13% ahead of eventual premiers North Melbourne. Survived Hawthorn by two points in the Second Semi Final. 27 points ahead of North at three-quarter time of the eventually drawn Grand Final. Never a real look-in in the replay. Phil Carman suspension probably cost them this one.
1979 - Finished third. Belted in the Qualifying Final by North. Did well to recover and reach the Grand Final - and to lose it by only five points - to a Cartoon side that had dominated the entire season. But what if the boundary umpire had been a bit closer to Wayne Harmes?
1980 - Finished fifth. Momentum filled run to the Grand Final but never a chance against you-know-who.
1981 - Finished second. Another Qualifying Final loss saw them have to do it the hard way and they did. 21 points ahead of Carlton at the 29 minute mark of the third quarter of the Grand Final. Over-run by fresher legs.
1990 - For all the excitement of a year in which they broke a famous drought, I always thought it was a bit of a nothing season where Hawthorn (five flags in nine seasons, 1983-1991) just had an off year. Essendon finished on top but the draw between Collingwood and West Coast in the Qualifying Final meant they had three weeks off, and were subsequently belted by Collingwood in the Second Semi Final. Swings and roundabouts. A nothing year fittingly finishes off with a nothing Grand Final. Drought over. A non-Collingwood man coaching the difference?
2002 - Finished fourth and my memory is they were serious underdogs against Brisbane and did well to go down in a close one.
2003 - The reverse of 2002. Collingwood finished second and belted Port Adelaide (who had dominated the season and finished on top) and again my memory is that they were a serious threat to Brisbane but never looked like it.
2010 - Best side all year. St Kilda were coming to the end of a very dominant but flag-less run (should have won it in 2009), and rallied to challenge the Pies in another drawn Grand Final. A shonky bounce in front of Stephen Milne could have changed it all. The Aints never a chance in the replay.
2011 - Finished 20-2 to claim the minor premiership but it was one of the most uneven seasons ever (West Coast finished 17-5, a record which would normally win you top spot, but only got them fourth; Brisbane's 4-18 landed them third-bottom!). Lucky to survive Hawthorn in the Preliminary Final and were running out of puff by the time they took on Geelong in the big one.
2018 - Ouch. Finished third three games and 16% below minor premiers Richmond. Played all over the Tiges in the Preliminary Final and were 29 points ahead of West Coast early in the Grand Final before the Eagles realized there was a game on. 12 points up three minutes into the last quarter. Thank God for an unpaid block and Sheed's goal. Should not have even been there.
In another world, Collingwood might have won flags in 1964, 1966, 1970, 1973, 1977, 1979, 1981, 2002, 2003 and 2018, but might have lost in 1958 and 2010.
I'm glad I don't barrack for Collingwood.