Following a stay in rehab Regal did return to the WCW for a little over a year before leaving the promotion in February 2000. Once again it wasn't long before Regal resigned with the WWE, but it was different this time as Regal was sent to the WWE's developmental territory for a short stint prior to heading to the main roster. This time around things were different and Regal would not only become the commissioner and a top heel, but he would really find stability for the first time in many years.
The reason for this edition of the series though is to focus on Regal's major run between 2007-2009 which is when he won the King of the Ring tournament in 2008. During that time Regal was a top heel in the company feuding with names like John Cena, Triple H, and Mr. Kennedy. This was most prominent position Regal had ever been in within the WWE and there was a rumor going around at the time that after his King of the Ring win Regal might've been in line for a reign as WWE Champion had he not gotten suspended. Though it might be hard for some fans to believe it is a possible situation considering the amount of heat that Regal would get at the time and his status within the company as a reliable hand.
Once he returned from the suspension he did win the Intercontinental championship soon after his status in the company would never again reach where it was in the above period of time. In 2009 Regal would be drafted to the ECW brand and though did once again reach the level of a top heel I'm not sure how much weight that carries considering the status of the brand he was on. His career was on it's last legs though as he would retire from active competition in 2014 becoming more of backstage/coach for the NXT brand. In my opinion there is very few talent better to help mold the new generation then someone who has been a member of this profession for as long as Regal has been. Either way though he is one of the many names that fans wonder what if when it comes to him holding the World Championship. The reality of it is though it might've just been a little "Too Little Too Late."