How a Hollywood legend lost $450 million as he didn't get the script, was forced into retirement after financial blunder
This Hollywood icon rejected a role that cost him $450 million, leading to a chain of events that led to his retirement in just over a year.
When Peter Jackson made the Lord of the Rings trilogy, not many supported what was seen as a 'crazy idea'. The books were considered hard literature, and many called them unfilmable. The plan of doing all three films back-to-back was also seen as excessive. On top of it all, the shoot took place almost entirely in New Zealand, thousands of miles away from Hollywood. Naturally, many top stars did not come on board. But the one who regretted it the most was former James Bond star and screen icon Sean Connery. The actor rejected the offer to play Gandalf in the films, and along with it, a multi-million dollar paycheck.

Why Sean Connery rejected LOTR
Sir Sean Connery was offered the role of Gandalf in The Lord of the Rings. As one of the most recognisable faces in the cast, he was to receive the highest pay as well. But Connery turned down the offer. According to IMDb, he did so due to "not understanding the story and the script". In the end, Ian McKellen came on board and made the role his own, reprising it in the Hobbit trilogy as well.

Peter Jackson had offered Connery $10 million per film plus 15% of the trilogy's gross for the role (that is, 15% of the studio's take, or 7.5% of the total gross). In the end, Lord of the Rings trilogy grossed $2.9 billion worldwide. This would have given Connery earnings of $450 million for the film.
How Sean Connery reacted to losing LOTR
Sean Connery was in his early 70s at the time. After Lord of the Rings became a global blockbuster, he regretted turning the film down. According to reports, he told his agents that if another IP-based script came in for him, they could say yes even if he did not understand the story. He was, reportedly, trying to avoid repeating a mistake. Through this process, Connery signed Stephen Norrington's The League of Extraordinary Gentlemen.

The 2003 release received extremely bad reviews but managed to be somewhat financially successful. However, Connery was so disheartened by the turn of events that he never acted again. He died in 2021, at the age of 90.