#1 Braun Strowman loses to Brock Lesnar (Crown Jewel 2018)

The most significant loss of Braun Strowman's career came at the first-ever Crown Jewel pay-per-view in November 2018. Brock Lesnar defeated Strowman for the second time in his career to win the Universal Championship.
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When Roman Reigns vacated the Universal Championship, The Monster Among Men took his position as the top dog. It was finally Strowman's time to break through the glass ceiling and become a mega-Superstar. Crown Jewel should have marked his coronation as the brand-new Universal Champion. Instead, The Beast Incarnate won the title.
The only upside was that it took multiple F5s and outside interference for the loss, but Strowman should've been the winner. He would have received an unimaginable boost by becoming Universal Champion and defeating Lesnar. His career could have taken off, and he could have headlined WrestleMania 35. Instead, Strowman's career took a downward trajectory, as he became just another guy in 2019.
Luckily, Braun Strowman did win the Universal Championship at WrestleMania 36 from Goldberg. However, it took place in the most anticlimactic way possible, and there was no live crowd. Had he won at Crown Jewel 2018, he would've received the reaction he deserved.