(DryShips poll, originally published Dec. 31, updated with latest news.)

NEW YORK ( TheStreet) -- DryShips ( DRYS) has reasserted itself as the name to watch among shipping stocks as CEO George Economou, true to his nature, steers his company into dangerous but potentially lucrative waters yet again.

Last month, Economou stunned the maritime industry by acquiring $770 million worth of new oil tankers. That's a huge and risky wager for the dry-bulk carrier.

On Monday, the first trading session of 2011, DryShips' stock received a downgrade from Morgan Stanley ( DRYS) analyst Ole Slorer, who views the tanker purchase with a jaundiced eye. He cut his rating to underweight from overweight. DryShips shares were down about 5% to $5.21 on heavy volume Monday afternoon.

The conventional wisdom has been that investors prefer pure-play shipping stocks. That is, they want their dry-bulk fleets (which haul coal, iron ore, grain and the like) separate from their tanker fleets, since the dynamics that govern each of those markets differ so significantly. A public company that owns both types of ship would only serve to make an already murky business that much less transparent -- and would hurt shareholders, since separate companies would fetch better values from the market.

Should You Abandon Ship?

Economou, of course, understands this. He therefore plans to spin off the tanker fleet into a new company through an initial public offering. In the meantime, though, he's essentially using DryShips itself as collateral. And, as history has shown, the company has had problems in the past spinning off businesses that it has told investors it wants to spin off.

(DryShips isn't alone here. Shipping magnates love to trade vessels and are constantly on the lookout for bargain ship prices. The normally conservative Diana Shipping, for example, has acquired containerships for what it believes are cheap prices, and has announced plans to sell that fleet off in an IPO.)

The Athens-based DryShips slogged through most of 2010 under a cloud of uncertainty caused by just such a situation. In another bold move several years ago -- some investors called it foolhardy -- DryShips made a multibillion-dollar bet on the energy business when it acquired a small fleet of so-called drill-ships -- portable rigs used to explore for crude oil in extremely deep waters.

The company's plan was always to spin off the drill business in an IPO as soon as it could. But it ran into trouble in 2010 when it couldn't find any takers from oil companies to charter out four new rigs it had commissioned from Samsung Heavy Industries, the big South Korean shipyard. That meant that DryShips couldn't find bank financing for two of those newbuildings. (The company had four drillships on order, but the other two were fully paid for.)

Finally, though, in November and December, a series of deals appeared to change DryShips' fortunes. First, it was able to ink charter contracts for two of its four newbuilding rigs. ("Newbuilding" refers to a ship on order and being constructed at a shipyard.) Then, it made up the financing gap by taking out a $325 million bridge loan and raising $350 million in an at-the-market offering of stock. DryShips has a checkered history of doing dilutive ATM offerings whenever its share price pops higher, which it certainly did after the company announced the rig contract.

Just on Tuesday, DryShips further steadied its drillships business by striking another series of charter deals worth nearly $590 million.

DryShips shares were rising 2% Monday afternoon in heavy trading. Only one of its four newbuildings remains without a charter contract.

DryShips has also secured options to buy four other drillship newbuildings. If the company ends up carrying out those options, it will have a fleet of ten rigs. The prospect has rejuvenated the bullishness of some sell-side analysts. "We expect these catalysts to push the stock higher as each additional event is another step closer towards DryShips successfully building a deep water rig company with scale," Credit Suisse shipping analyst Greg Lewis wrote in a research note in mid December. He boosted his 12-month price target on DryShips stock to $9 from $5.

If the rig controversy has cleared to some degree, investors must now contend with DryShips' huge oil-tanker bet. The deal will give the company 12 ships, all still in the midst of construction at a Korean shipyard, and due for delivery between 2012 and 2013. DryShips said it would pay for the vessels with its own cash and with bank loans.

The company's stock, meanwhile, has grown volatile once more after spending months in the doldrums. Average daily volumes have spiked. Since Nov. 1, the stock has ranged between $4.06 and $6.44. It was trading on New Year's Eve at $5.50.

So what do you think? Will Economou's gambles pay off for shareholders in the end? Click to below to take our poll on where DryShips stock will be trading by the end of 2011 -- and to see what TheStreet predicts for the stock in the coming year.

Where do you see DryShips stock trading by the end of 2011?

Below $5
Between $5 and $10
Between $10 and $15
Above $15

-- Written by Scott Eden in New York

>To contact the writer of this article, click here: Scott Eden.

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Disclosure: TheStreet's editorial policy prohibits staff editors and reporters from holding positions in any individual stocks.

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