Despite riding the bullish wave amidst the entire Covid saga, when we look back in the rear-view mirror we come across a handful of promising names, once the 'darlings' of yesteryears' bull market, who lost their charm; leaving a sour taste in the investors' mouth. These fallen angels together are responsible for wiping out a whopping Rs 60,000 crore of shareholder wealth in just a matter of four years. This number is as big as Motherson Sumi’s entire market capitalisation or even about half of Zomato’s, as of today. Let that sink in!These once magnanimous large, mid-caps are either already a penny stock trading in single digits or are on the brink of becoming one, except for Zee who was recently saved by the Sony merger!Now, bear in mind, that these are just a few names off the top of our heads. In reality, there could be a lot many names that could be added to this list of 'the biggest and most notable market failures', pushing the Rs 60,000 crore losses mark even higher.Surprisingly, all these businesses had one thing in common, they were the absolute darlings of the bull market and created all the buzz back in their days; for their respective prospects of course. In fact, not a single soul could have predicted that anything could go wrong with them. One just had to invest in one or even a basket of these dozen-or-so promising businesses, hold them for a few years and count the gains!But no one could have imagined what came next! When a business lists itself publicly, it sure can bring in an instant flood of capital, but we as investors fail to grasp that it also opens up the business to greater public scrutiny, airing out albeit not all but most of the company’s dirty laundry. And this becomes the duty of the investor to diligently study the company, its business and especially befriend its numbers which have the immense power to convey the honest truth, the real inside story, rather than the one being sold to them constantly by the media and company reports.Read Here | M-cap of top-10 valued firms jumps over Rs 1.56 lakh crThe list is full of classic examples wherein investors fell for a story rather than an attractive quality business at a reasonable price.Apart from the whispers of profit and loss, and balance sheet, fudging with practices of aggressively boosting revenues and conservative booking of bad debts; a few other commonalities we noticed with the majority of these dimmed stars were massive borrowings (debt), lofty promoter share pledges accompanied with a negative return on capital employed and cash flow from operating activities. We are barely scratching the surface here but as one may suspect, there’s also an independent crisis story unfolding behind each of these monster-sized setbacks. But we wouldn’t get deeper into that as most of us are well aware of these downfalls. But when we take a step back and look at these businesses collectively we notice that most of these stories show us the dangers of unmet and unrealistic expectations rooted more in hope than plausibility.With that as the backdrop, here’s a run-down of a few of the biggest and most notable market failures from the past four years. And even though we’re sure that the numbers may change going forward, but one thing we’re sure about is that it is unlikely that any of these stock flops will perform their way off of the list, at least anytime soon.Cox & Kings, once a household brand name in India and directly compared to Thomas Cook, got its name tarnished with the alleged accounting frauds. Losing over 99 percent of its value, the company is now in shambles!Read Here | We may be over-worrying about rising treasury yields, here's why India’s largest fitness group, Talwalkars, which was considered to be a steady, conservative and successful enterprise also wound up shredding 99 percent of its value in the last four years. The fitness group borrowed massively along with pledging nearly three-fourths of the promoter shareholding.Analysts salivated at the prospects of the Adlabs Initial Public Offering (IPO) back in the day with newspapers covering articles like 'Top 5 reasons why Adlabs is good for long-term investors'. Adlabs Imagica once touted as the Disney Land of India also lost about 86.6 percent of its total market capitalisation.YES Bank’s technological prowess was supposed to be a strategic business enabler to build distinct competitive advantage as well as provide better products and services but immediately after its peak, it began lending to companies that were under stress, including the Anil Ambani Group, DHFC, and the Zee. Long story short, eventually the debts kept piling up leading to more and more non-performing assets. Ironically, the helping hand of YES Bank also got pulled down during this entire debacle to make its way to the list of dreadful market failures.Interestingly, about 40-50 percent of these companies’ holdings stood solely with retail investors. And as we already know promoter pledging was huge, proving they absolutely had no skin in the game whatsoever. What’s even more daunting is the fact that the majority of these pledged shares lay with government banks!Clearly, a lot can go wrong even with the biggies as they can quickly fall out of favour. So, go back and check again if you are sitting on today’s Adlabs, Talwalkars, perhaps Jet, or even RCom! Tread carefully, these are dangerous waters! Do not give in to tempered enthusiasm and always invest diligently; ensuring that occurrences like these do not run you off the road, but instead only remain mere speed bumps on your way to immense wealth creation!—The authors, Koushik Mohan, is a fund manager at MoatPMS, and Salonee Desi, is a senior equity research analyst at MoatPMS. The views expressed in this article are their own.