It's a fitting metaphor for the dying days of WCW, the ubiquitous 'On A Pole' match, which creative head Vince Russo re-popularised in late 1999. Swerve! It was never popular.
Judge it against the competition, with which WCW was locked in a battle for supremacy and, eventually, survival. The WWF implemented Hell In A Cell as its trademark unique battleground; with the odd RAW exception, the steel structure throughout the Attitude Era was only lowered to settle the fiercest of rivalries, and on the most special of occasions. The match invariably delivered because it was bloody, epic and spectacularly brutal. The mere association of a wrestler with the stipulation raised their stock: only the biggest of stars entered the battleground.
In contrast, WCW's branded 'On A Pole' match, in which an object of some (typically baffling) description was erected above the apparatus, became a rite of passage en route to failure. The pole appeared on virtually a fortnightly basis at one point, contriving to normalise possibly the most mundane stipulation match imaginable. The Pole match was a ladder match sans the brutality, tension and high spots. It was a climbing contest, an elevator to nowhere.
The 'On A Pole' matches weren't just searingly idiotic, in and of themselves; Russo didn't know, nor care about, the rules...