This may look like a fleet of drybulk carriers with a couple of semi-submersible oil-drilling ships tossed in, but shareholders can tell you it's actually a naval flotilla in disguise, firing painful cannonballs of debt and dilution.

The flotilla in question is DryShips (NASDAQ:DRYS), under the devastating command of enigmatic CEO George Economou. Controversial business transactions, in which Economou has an interest on both sides of the handshake, are nothing new here. Colleagues such as Genco Shipping & Trading (NYSE:GNK) CEO Peter Georgiopoulos criticized the magnate and other shippers for playing "games with their shareholders' money."

DryShips' latest move feels like pouring salt into shareholders' gaping wounds. Less than two months after I took him to task for quadrupling the company's share count, Mr. Economou is tossing fiscal conservatism to the wind and directing DryShips to purchase the final 25% stake in the company's drillships subsidiary, Primelead Shareholders. The deal, which converts Primelead to a wholly owned subsidiary, is being touted as an accretive move to bring 100% exposure to future cash flow from the promising drillships industry.

I concede that the company's two existing drillships, and four similar vessels presently on order, are the new stars of DryShips' fleet, now that the dry bulk sector has entered troubled waters. With hire rates like the $575,000 dayrate paid by Petrobras (NYSE:PBR) for one of the existing rigs, no one is denying the cash flow potential from these assets. But the unrelenting aggressiveness of Economou's quest for growth through all stages of the business cycle gives me pause.

With a $2.85 billion cloud of debt hanging overhead, I believe the company can ill afford the $50 million cash expenditure the deal requires, to say nothing of the $280 million in convertible preferred stock that will become as many as 46.2 million common shares. The preferred shares will convert at a premium to the present share price, and also carry a dividend yield of 6.75%, payable in yet more convertible preferred shares. If you're wondering who stands to hold these new shares, you may have already guessed it: a company controlled by Mr. Economou himself is among the sellers.

I've given up trying to guess at a line that this guy won't cross, and in anticipation of the usual speculative fervor over his dealings, I've even added DryShips to my CAPS portfolio just for fun. I do not, however, consider DryShips a safe investment vehicle. I believe investors seeking exposure to deepwater drilling would be better served by the likes of Transocean (NYSE:RIG) or Atwood Oceanics (NYSE:ATW), while Navios Maritime Holdings (NYSE:NM) offers similarly bold growth initiatives without the massive debt load.

Further Foolishness:

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Fool contributor Christopher Barker used to captain yachts somewhat smaller than dry bulk carriers. He can be found blogging actively and acting Foolishly within the CAPS community under the username TMFSinchiruna. Atwood Oceanics is a Motley Fool Stock Advisor recommendation. Petroleo Brasileiro is a Motley Fool Income Investor pick. Try any of our Foolish newsletters today, free for 30 days. The Motley Fool has a seaworthy disclosure policy.