The Undertaker's working relationship with WWE is an interesting situation these days.
Things between the two sides changed greatly when Taker was announced for the upcoming Starrcast II convention, according to the Wrestling Observer Newsletter. The Observer also notes that people in WWE were at first saying there was no way Taker would appear at Starrcast, but he is making the appearance likely to due to contracts.
Taker reportedly thought his WWE career was over after the matches in late 2018 - the No DQ loss to Triple H at WWE Super Show-Down in October and the tag team match at WWE Crown Jewel in November, which saw Taker and Kane lose to WWE Hall of Famers Shawn Michaels and Triple H, and that's when he started booking non-WWE paydays. Vince McMahon was upset when the Starrcast appearance was announced, but WWE reportedly made Taker an offer he couldn't refuse, financially, once things calmed down between the two sides. Part of that new contract was an agreement that Taker could no longer work the outside dates, except for the ones he had already booked.
The Observer notes that Taker had no legal way to get out of the Starrcast deal, but for the UK deal with Inside The Ropes, they didn't have the king of legal resources to fight WWE on it. Regarding those ITR appearances on April 29, April 30 and May 1, Taker was originally scheduled to meet fans for autographs and photos, plus a Q&A session. That was changed last week, and it was announced that WWE Hall of Famer Mick Foley would be doing the Q&A part of the show, while Taker would be appearing for just the signings. This is because of the new WWE deal that Taker was signed as the company wanted to bring him back into the fold. Taker reportedly "pushed really hard" to keep the Inside The Ropes appearances, despite people in WWE not wanting him to go at all. The promoters would have had to refund all tickets and it could have really hurt them moving forward, and Taker did not want to do that. That's when the compromise was made with Foley coming in to discuss his history with Taker each night. The Observer adds that Taker pushed to make sure he still came for at least the signings with fans.
There was a feeling that WWE believed Taker would never take bookings with people the company didn't want him doing dates with, and WWE didn't realize the large amount of money that some promoters would offer Taker for their events. It was reported in February that Taker was charging $25,000 per hour, and that he would have no trouble finding dates.
One source involved in booking non-WWE appearances noted to The Observer that the $150 per person price to get a photo and autograph with Taker was actually too low as WWE Hall of Famer Steve Austin charged $316 for his VIP package at WrestleCon in New Orleans last year during WrestleMania 34 Week, and they had so many requests at that price that they were overwhelmed and had to cut sales off. There was a feeling that Taker could have had a similar demand at WrestleCon during WrestleMania 35 Week this year. Taker was approached by promoters for WrestleMania 35 Week appearances, including WrestleCon, but he had already agreed to do the post-WrestleMania RAW appearance.
It was also noted that it's still not clear if Taker's new WWE deal is to wrestle, but he's expected to return to the ring at the next Saudi Arabia event, believed to be on Friday, June 7. A match with Elias has been rumored after their recent run-in on RAW, but that could have been changed now that Elias was moved to SmackDown in the Superstar Shakeup. Taker is also scheduled for a signing appearance that Sunday, June 9th at the Niagara Falls Comic Con in Niagara Falls, Ontario, Canada.
Source: Wrestling Observer Newsletter
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