#2 His WWE Championship reign
Where do I start? The IWC had been backing Ambrose for a long time, and fans were clamoring for this inmate to one day run the asylum, but it seemed as though WWE would never pull the trigger.
At Money in the Bank 2016, Roman Reigns defended his WWE Championship against Seth Rollins, but first Dean Ambrose won the Money in the Bank briefcase. After Rollins beat Reigns, Ambrose stormed down to the ring to cash-in the briefcase and beat the newly crowned champion for the title.
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Fans were ecstatic as the dream of all three Shield members holding the WWE Championship on the same night became a reality. While Ambrose's coronation as champion was perfect, his reign was not.
Ambrose was drafted to SmackDown Live during the brand-split, and successfully defended his title in the Shield triple threat at Battleground. After bringing the most prestigious title in all of wrestling to SmackDown Live, Ambrose was shown in a comedic segment where he nearly left the championship in the back of a cab....the precursor of a lackluster reign.
Ambrose was made to look like a fool on Miz TV, was not made more serious and never abandoned the wacky lunatic persona he has been burdened with. A promising rivalry with Dolph Ziggler somehow failed to live up to expectations and before we knew it WWE was going all in on AJ Styles.
After earning a shot at the WWE Championship Styles low blowed Ambrose when the ref wasn't looking and put the champion away with the Styles Clash. While the matches between Ambrose and Styles were stellar, its a shame to see Ambrose lose the title to a low blow and fail to reclaim it due to betrayals.