I honestly think Barbara's swap was FAR worse than Orry's swap. Orry was
extremely sentimental and emotionally attached to his late brother's birthday box, so we all kind of saw it coming. Barbara's decision to swap on the other hand was just a complete spur of the moment thing and her reaction at the reveal was so sad as she was so overcome with shock at the consequences of her decision that she could hardly speak fluently and you could tell she was holding back tears at the end
Jim who played the day before notorious Donna was another one from that era. He'd gone to the end with a £250/£20k finish and he swapped it on the basis that £20k had been on the table for the last 2 games, but sadly, it would've been 3 if he kept his box. I heard Jim took his loss quite badly and completely broke down in tears after the game
Esher was made worse by the fact that she'd had one of the strongest 5-box boards of all time (£1k/£35k/£75k/£100k/£250k and a sub-par offer of £60k) and at the time, we were practically
starved of big wins. It'd been 2 months since someone had a power-5 level win and Esher could've broken that drought by either keeping her box or dealing at 5-box, and sadly, the power-5 win drought would continue for another 2 months after that
PJ and Matty's 17-box swaps also come to mind as they both swapped a life-changing amount for 1p and won it. But both games were also controversial with the banker's shock tactics in PJ's game and Matty going from being cocky at the beginning of his game to looking like he was on death row after the game crashed and he realised the error of his swap
£5k Matt just before Barbara is also up there as Matt took it quite badly when he swapped a £50k box for £5k, and it also felt like a real letdown after Matt had the strongest start in the history of the show