According to an incredibly detailed article in Newsweek, MIBSL is indeed an homage to Walt Jabsco, better known as the iconic logo for The Specials, which itself was based on a photo of a young Peter Tosh when he was in The Wailers (read more about the art design of 2-Tone here and an interview with the graphic designer who helped create Walt Jabsco and 2-Tone art here).
The origins of MIBSL can be traced back to the late 1990's when Microsoft was developing Internet Explorer 4.0 which for the first time included a new font called Webdings that enabled users to swap letters on the computer keyboard for tiny proto-emoji. One of them, which was paired with the letter M (perhaps it was a take on the Madness logo?) looked like the images below:
Vincent Connare who was working in the Microsoft typography department:
"After deciding to incorporate Webdings in the browser, the Internet Explorer team and Connare’s manager, Simon Daniels, drew up a list of symbols to design, mostly stuff that might look good on a website in 1997. Connare went down the list, selecting the ones he was interested in. One option immediately stood out.“I had a Specials Japanese import LP, and I saw one of the keywords was ‘jump’ so thought it would be good to make a jumping, pogoing man,” he said. “The style of the 2 Tone guy was black on white, and it was graphic, so it was easy to make something like it into a font.”And so 17 years later, in late 2014, the Unicode Consortium (which determines which emoji are approved for use), announced that Version 7.0 would include adaptations of the original Webdings characters. And that my friends is how the pogoing rude boy emoji somehow got stuck with the silly levitating businessman moniker!