Caremark's Boardroom Break

Caremark's (CMX - Cramer's Take - Stockpickr) lead director, Roger Headrick, is sporting another black eye.

This time, the shiner came from a Delaware judge who would like to see Headrick explain his recent actions. Headrick and his fellow Caremark board members have unanimously endorsed an unpopular merger with CVS (CVS - Cramer's Take - Stockpickr) while altogether shunning a competing -- and potentially better -- offer from rival pharmacy benefit manager Express Scripts (ESRX - Cramer's Take - Stockpickr). The directors face bruising criticism as a result.

But that's not why the judge is asking for an explanation. Last week, Delaware State Chancellor William Chandler found himself musing about the director's whereabouts instead.

After Headrick's lawyers tried to change the director's deposition schedule with Express Scripts' lawyers, Chandler upheld the original schedule -- and expressed some irritation at having to do so.

You "offer no explanation regarding director Headrick's reasons for being in New Zealand or 'difficult to reach' during an especially critical period in the life of the company on whose board he serves," Chandler wrote Thursday. "The Court can only surmise that the reasons were personal in nature.

"That does not suffice as a reason to require a flock of lawyers to travel to a location convenient to a single director of a public company," the judge continued, "especially when the inconveniences of a directorship are part of the job."

Caremark didn't respond to requests for comment. But for Headrick, the inconveniences of part-time work on the Caremark board have paid off handsomely.

As one of Caremark's longest-serving directors, Headrick has seen the company through both good times and bad -- with a core business going bankrupt early on -- and picked up plenty of valuable stock options along the way. His current stake in Caremark, including stock and options, is worth more than $150 million right now.

By now, Headrick is no stranger to controversy. Indeed, he seems to come under attack wherever he goes, whether he's running the fierce Minnesota Vikings or scrambling to save the lovable Pillsbury Doughboy.

His record at those places could offer some guidance to Caremark shareholders searching for clues about his role in the CVS-Express Scripts battle.