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He's stated it multiple times with certainty on WOR and in the Newsletter that it expires on the 31st and has given no indication that it might not. That is not to say that he hasn't resigned but as now the public knowledge is that his deal expires in 3 weeks and he is thinking things over.Dave Meltzer, for what it's worth (and he happens to be wrong A LOT) also said on Wrestling Observer Radio that people in New Japan have also indicated that Kenny Omega has already resigned a long term deal with them. So he basically covered his ass by saying both his contract may expire and may not expire on January 31. Regardless of what Kenny does, he can say he was right.
Kenny Omega is not coming to WWE anytime soon. He is not an idiot. He is the second biggest star in NJPW right now. He was the first gaijin to win the G1 Climax. That alone tells him how NJPW values his worth. He will undoubtedly be a future IWGP Champion. With his personality, if he came to WWE, he would be turned into a complete joke. Vince would likely enjoy his more outrageous behavior BUT he wouldn't take Omega seriously. If he signed Omega, it would simply be to take him from New Japan. He would likely have a good first couple months and he would become Gallows and Anderson.
I don't know how you can even say that with a straight face when you look at the success AJ Styles has had over the last year and the quality of his booking, he started off a little shaky with that Mania loss to Jericho but both Roman Reigns matches had very heavy interference and he was kept to look strong in both those bouts so he truly never lost clean to Reigns, he beat Cena at MITB (Despite interference yeah) and then at Summerslam pinned Cena clean and at No Mercy he beat both Cena and Ambrose. Styles is currently the World Champion and there is a very strong chance he walks into Mania as the champion and main events it if the current speculation of Braun Vs Taker (After last nights Raw) is true. Omega currently is in a very similar position to Styles so if he left for WWE then it would be without a doubt a good run on the level of Styles, if Omega leaves for WWE I see him being the guy that Cena puts over for the belt when he beats Styles.
Anderson and Gallows you've got to understand are not in a bad position, everytime they lost to New Day was from bullshit finishes and that wasn't an issue with Gallows and Anderson, that was an issue with the entire tag team division because of New Day. Anderson and Gallows suffered from bad timing and there is always a very short ceiling you can hit as a tag team wrestler anyway, its not like a singles feud where you can have an amazing feud like Cena and Styles without the belt. The tag team division has always suffered from awful booking and lack of story behind the matches so its hardly like Gallows and Anderson are individual cases its just a symptom of being in the tag division.
Another aspect is that Omega would be making a lot more money in WWE and that is a big temptation, as much as New Japan values him they won't pay him what WWE would pay him.
I don't know why you think Omega would be booked poorly, look at the last two men in similar positions to Omega that joined WWE. Devitt and Styles, Balor went on to have the longest NXT Title run, put the brand on the map, join the main roster, beat Roman Reigns clean after a previous fatal four way match and then go on to beat Seth Rollins clean and was positioned to be WWE's top babyface for Raw until he was sadly injured and then AJ Styles who is currently the WWE World Champion having pinned John Cena 3 times and only one of those was from outside causes. (You can say he tapped at No Mercy but he was in a double submission so you can make the argument that it was a smart heel move to escape the hold and the chair he used is entirely legal in Triple Threat matches so technically it was clean in my books). If Omega left for WWE there is zero doubt in my mind he would follow the same path they did.