#3 Triple H seemed like a perfect fit to hold the Money in the Bank briefcase
One of the most opportunistic Superstars in WWE history, Money in the Bank would have helped Triple H rise to stardom. He'd have been the biggest beneficiary of it, through manipulation and perfect timing. The Game's cunning demeanor seemed perfect for the briefcase.
He has experience in big ladder matches, defeating The Rock for the Intercontinental Championship in 1998. Triple H could have repeated the feat with the Money in the Bank briefcase being up for grabs.
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The Game's Money in the Bank victory and cash-in would have garnered significant heel heat from WWE fans. It may have come at the expense of Mankind at SummerSlam 1999. Triple H could have won the WWE Championship immediately after his victory, instead of waiting for RAW the following night.
Alternatively, the likes of DX and Stephanie McMahon could still have played a role in his Money in the Bank cash-in either side of it. Triple H could have been an effective briefcase holder up to 2002. He could have traded it for the brand new World Heavyweight Championship, instead of simply being handed the belt.