Yesterday, I highlighted the three best moves in gaming over the last couple of years. It's easy to see how executives made smart decisions when their stock prices were rising, but we should also look back to see why their stocks were in the dumps to start with. Here are the three worst moves in gaming during the last half-decade.

Sheldon Adelson sticks it to shareholders
Las Vegas Sands
(NYSE: LVS) CEO Sheldon Adelson has gotten a lot of credit for his vision in Asia. But in 2008, with the stock price tumbling, debt covenants choking the company, and the economy plummeting, Adelson failed to act quickly to stop the bleeding. Maybe he thought customers would come back in time, or maybe he ignored executives' pleas for him to raise cash, but in the end, Adelson deserves the blame for Sands' massive stock fall.

He could have made the sort of dilutive stock offering the company needed at any time after shares hit $140 late in 2007. Instead, he waited until it was almost too late. As a result, shareholders took a massive hit, and the company nearly went bankrupt. But Adelson himself took a big part in the offering, including shares of preferred stock and warrants, so his portfolio took a much smaller hit. It's funny how things work in your favor when you call the shots.

Adelson is a great CEO to have when the economy is booming and aggressive risk-taking is the order of business. But when times are tough, Wynn Resorts (Nasdaq: WYNN) CEO Steve Wynn takes shareholders' interests much more to heart.

MGM from 2007 – 2009
Missteps at MGM Resorts (NYSE: MGM) abounded toward the end of ex-CEO Terry Lanni's days at the helm. He presided over the design of the worst investment in gaming, CityCenter, which would be enough to make anyone's tenure look terrible. But when billionaire and MGM investor Kirk Kerkorian offered him a way out by splitting CityCenter and Bellagio into a separate company, Lanni couldn't make the deal happen. It would have been perfect timing, since the housing market was peaking and casino stocks had never been higher, but Lanni missed the opportunity.

That inaction helped lead to the fire sale of Strip property Treasure Island to Phil Ruffin a year later, when MGM needed cash. And while further stock offerings and asset sales have put the company in a better financial position, this is the only major casino company that still raises questions regarding its survival.

Private equity falls in love with gaming
Now for my favorite private equity purchase of all time: The Apollo Management/TPG Capital buyout of Harrah's Entertainment, now known as Caesars Entertainment. The $27.8 billion deal was completed in early 2008, near the peak of the stock market, when gaming veterans had their eyes elsewhere. By the time the purchase went through, Las Vegas Sands, Wynn Resorts, and MGM had joined Melco Crown (Nasdaq: MPEL) in building casinos in Asia, where growth shot through the roof.

After the company barely survived the recession with the help of some financial magic and the largesse of its debtholders, the market laughed when Caesars wanted to go public. The private equity firms took a risky bet, and so far, they've come up empty.

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