Terra Fallin'
Helmsley, meanwhile, had debuted in the summer of 1995 as a somehow more entitled younger version of the Million Dollar Man; while it seemed like Dibiase had somehow earned his wealth (most likely through some very 1980s Wolf of Wall Street shenanigans), Helmsley was portrayed as the heir to a great deal of generational family wealth.
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Helmsley was Connecticut Old Money, the type of people McMahon now counted as neighbors (and, reportedly, hated, despite his own showy affluence and running a family business). Upon completing his feud with Corporation member Sycho Sid, Godwinn and Helmsley began feuding for rational and well-founded personal issues featuring nuance and depth.
Either that, or Helmsley and Godwinn were thrown together because the clash between their characters gave McMahon, on commentary, loads of opportunities to shout, "Yee-haw!" and revel in the embarrassment of a stand-in for his neighbors.
Helmsley and Godwinn fought on opposing Survivor Series teams at the 1995 edition of the event, Godwinn on an Undertaker-led Dark Side team united only by onscreen babyface alignment and backstage boredum busters, and Helmsley on Jerry Lawler's Royals team, featuring Lawler, Helmsley, "King" Mabel, and the evil dentist Isaac Yankem, D.D.S.
The match featured some back-and-forth between the two teams until 'Taker (presumably) decided, "This is dumb," and eliminated all four members of the opposing team in quick succession. Helmsley was the third (and last in-ring elimination), falling by chokeslam before Mabel ran away in fear.
Because of the bad blood still simmering from this match reasons, Helmsley and Godwinn continued their feud into December, with Helmsley attacking Godwinn after a match and Godwinn retaliating by slopping himself before a Monday Night Raw encounter to ensure the rich boy would encounter the maximum amount of filth in their matchup.
Helmsley slipped repeatedly on the slop, meaning one would reasonably assume the heel was embarrassed enough to end the feud. Regardless, it was announced that the pair would finally settle their differences in the company's first ever Arkansas Hog Pen Match at the December In Your House event.