#2 Velveteen Dream asked to join WWE RAW/SmackDown
Velveteen Dream took an enormous gamble in August 2018 when he sent a message to Vince McMahon during his match against EC3 at WWE NXT TakeOver: Brooklyn IV by wearing tights which contained the words ‘Call Me Up Vince’.
This match happened over a year before WWE NXT moved to the USA Network and became a legitimate rival to WWE RAW and WWE SmackDown in a storyline at Survivor Series 2019.
At the time, it was common for NXT Superstars to move to RAW or SmackDown in the days following WrestleMania and SummerSlam, which is presumably why Dream chose a match on SummerSlam weekend to grab the attention of McMahon.
Triple H, who had not seen Dream’s tights before the match, said he admired the former Tough Enough contestant’s willingness to take a risk, but he was unsure how WWE's Chairman would react.
"If he is talking about Vince McMahon, there are a couple different phone calls you could get from Vince McMahon. One you want to get, one you really don't want to get. So you have to be careful when you say, 'Vince, give me a call.' Because you never know what kind of call you're going to get." [H/T Wrestling Inc.]