From flash crashes to the flash-fire contagion of credit distress, investors are busy weighing their perceptions of risk against the opportunities in well-selected stocks. Voluntary exposure to risk can have its place ... so long as those risks are well understood.

DryShips (Nasdaq: DRYS) -- that enigmatic, much-transformed shipper with a vehemently loyal following -- provides the ideal example of a stock pick where perhaps both risk and potential reward approach the limits of the imagination. I have long considered this one of the scariest stocks from any sector, but lost between the lines is my corresponding acknowledgement of the potential reward.

Curious George antes up
Believe it or not, the stakes keep climbing. If the initial foray into the ultra-deepwater drillships sector with the Ocean Rig acquisition were not a large enough gamble for a dry bulk shipper, CEO George Economou has doubled down with options to build another four drillships for delivery in 2013 and 2014. Representing a notional outlay of $2.4 billion, the move raises the specter of persistent debt distress for a company that has already put its shareholders through the ringer.

Even before delivering on the long-anticipated spinoff of that venture, the company boldly charged into the oil tanker business with a $770 million venture to acquire 12 oil tankers. Morgan Stanley analyst Ole Slorer downgraded the stock in response, stating that DryShips "has become difficult to value."

Moderating that expanding risk profile somewhat, DryShips has scored some very critical contracts for all but one of the first four newbuilding drillships. The newly delivered Ocean Rig Corcovado secured a six-month contract worth $142 million, with the charterer also contracting the semisubmersible rig Leiv Eriksson for $95 million. Corcovado's sistership, Poseidon, will be employed by a subsidiary of Petrobras (NYSE: PBR) for a 600-day stint generating $353 million in revenue.

Understanding the stakes
Given the company's unfortunate track record for woeful share dilution, excessive debt exposure, and often opaque dealings that leave many onlookers wondering whose interests are being served, Fools are advised to assess the stakes carefully before considering a gamble with DryShips.

First and foremost, it must be understood that DryShips is no longer primarily a dry bulk stock. Before rolling these dice, be sure you like the odds for improvement in three separate segments of the maritime industry: dry bulk, ultra-deepwater drilling, and now oil tankers. With the Baltic Dry Index mired in persistent weakness, it's clear that segment has yet to work through an epic oversupply situation. On the flip side, one could argue fairly effectively that these recent drillship contracts provide a powerful counterpoint to the thin operating margins presently descending upon pure-play dry bulkers like Baltic Trading (NYSE: BALT).

Like a gambler who borrows from the house to sit at the table, DryShips is acutely leveraged with debt. The company's $1.7 billion market capitalization cowers beneath the shadow of a debt burden that will likely stand well above $3 billion once the recent $325 million bridge loan for the Corcovado and forthcoming installments on the tanker fleet are added to the tally. If worst-case scenarios were to play out in the global credit markets, highly leveraged companies like DryShips enter stormy waters. On the other hand, a landmark financing deal between China's new $5 billion shipping investment fund and DryShips suggests the company may have some key allies interested in keeping the operator afloat. Fellow Greek shipper Diana Shipping (NYSE: DSX) has noted the strategic importance of China's investment initiative in securing the outlook for these embattled shippers.

Pondering the payday
Now that we've contemplated the ways one can lose with a bet on DryShips, it's time to consider the potential gains from a successful outcome for Economou's unabashed quest for countercyclical growth. After all, it was not long after I warned investors of the debt-driven dangers of Teck Resources (NYSE: TCK) that the stock catapulted straight through nine-bagger status to stand today at a 24-fold gain from its multiyear low. We wouldn't call it gambling if the potential gains were not substantial.

In a jackpot scenario where DryShips manages to build a backlog of contracts on these first four drillships, which could in turn funnel capital into the exercising of options on the additional vessels, a forward-looking Fool can begin to see just how massively undervalued this 78%-owned Ocean Rig venture may arguably be. If such conditions were to be accompanied over time by improving market conditions in both the dry bulk and oil tanker segments, one could conceivably see these embattled shares shooting for the moon. Since DryShips has already diluted its share count a gut-wrenching 11-fold during its first five years as a publicly traded company, one might tentatively surmise that the worst of that activity must certainly lie in the past.

In parting, I would remind Fools of the principal advantage inherent in a truly high-stakes bet: Even a modest wager that one is prepared to lose outright can conceivably deliver that delightful surprise with a legendary multibagger return. I will continue to rely upon far safer resource plays like Peabody Energy (NYSE: BTU) and BHP Billiton (NYSE: BHP) to form the conservative core of my commodity-related exposure, but risk-ready Fools seeking a high-octane vehicle for overlooked growth potential may wish to give DryShips' roulette wheel a spin.

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This article represents the opinion of the writer, who may disagree with the “official” recommendation position of a Motley Fool premium advisory service. We’re motley! Questioning an investing thesis -- even one of our own -- helps us all think critically about investing and make decisions that help us become smarter, happier, and richer.