Its only natural to have regrets about 2020. They played it very conservatively and that looked to be a fine strategy, but Pog decided to make his entrance. You can't account for that really, nobody did, because Roglic had shown previously that in theory he should be the hot favorite to win a stage like that, so the time gap seemed like it should be enough 95 of 100 times. Thats bike racing and Pog won it fair and square, but that was obviusly a big blow for him as he was the best GT (or at least considered) in that season specifically. He was the man.When Roglic does retire, hopefully he doesn’t have any regrets about the Tour de France. Especially 2020 and 2024. He’s had a stellar career if a win doesn’t come up in the future and can add his own piece of history winning TdS next year.
2021 was more a case of 50/50 on paper going into the race, but everything suggests to me Pog would still have made a different to Grand Bornand. From there on its everyone's guess whether he could claw back some time. With Jonas being extremely good, and Pog looking human later in the race, Rog could have made a really interesting race and could have won the race potentially. Jonas stood no chance, but Rog would have made it closer.
2022 I think his overall level was visibly lower than 19 and 21 and specifically 20 and Jonas was flat out just stronger. He contributed to his downfall on Galibier, but Jonas would in all likelyhood still have won. He was simply the best rider in the race, so no regrets here IMO. It was out of reach due to his level being a bit lower and Pog and specifically Jonas being mutant.
2024, realistically he was in trouble on every single stage that mattered from San Luca, Galibier, Troyes and Le Lioran. To make matters worse he wasn't actually respected as a genuine contender to win on San Luca (they visibly slowed), Galibier (UAE could have put the nail in the coffin) or Troyes (was dropped multiple times, but Visma and UAE didn't seem to care that much about it). Put in a very good effort in the TT, but unless Pog and Vinge crashes or has HUGE offdays, he wouldn't stand a chance of winning the whole thing, but after Le Lioran he looked like a slight favorite for podium against C-Rod and Remco which IMO was the best display of the season.