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Airline mergers can be logistical nightmares. The companies are huge operations, often with completely different corporate cultures, operating under a clutch of conflicting union contracts. But when Northwest Airlines Corporation agreed to tie the knot with Delta Air Lines, Inc., in April, the risk loomed especially large for Northwest. Powerful politicians vowed to try to block it even before the parties signed. The deal can be shot down by the U.S. Department of Justice's antitrust review. And, finally, there was one contingency that would cost the airline dearly just for signing the agreement, even if the pact failed to close: Northwest would lose its "golden share." [See "Crash Landings."]

Though it sounds like something out of a Harry Potter novel, the golden share was real enough. It consisted of preferred stock in Continental Airlines, Inc., which gave Northwest the right to block its competitor from most mergers. Northwest acquired it in 2001, after it bought a controlling stake in Continental-only to be sued by the Justice Department's antitrust division, which forced it to sell back all but the golden share. And it gave Northwest valuable leverage in an industry with, at least these days, a permanent urge to merge. But because Northwest agreed to the marriage with Delta, it had to sell it back to Continental for the grand sum of $100.

None of this blindsided Northwest's CEO, Doug Steenland, or his counterpart at Delta, Richard Anderson. For one thing, they're lawyers, so they "get" the intricacies of such issues. In their case, it was an important part of the merger negotiations. Why? As soon as the partners signed, Northwest lost that valuable weapon, which meant that it had more riding on the deal's successful outcome than Delta. Yet, Delta, as the surviving company, would have complete control of the regulatory approval process that would determine whether the merger did, in fact, close. Delta's Anderson recognized that this put his merger partners at a considerable disadvantage and upped the stakes for them if the deal fell apart. "They had to have some real certainty they were going to get across the finish line," he says. So he broke with convention and invited Steenland to head the regulatory process.

Anderson had confidence in his offer because he knows his counterpart well. They worked together at Northwest for 15 years. From 2001 to 2004, Anderson was the airline's CEO and Steenland its president. And when Anderson says that Steenland is "fantastic at the regulatory process," it isn't mere flattery. Steenland began his career as a Washington lawyer, and he knows his way around Capitol Hill.

It's not every day that the CEOs of two merging companies turn out to be lawyers-statistically, in fact, only 7 percent of the S&P 500 CEOs have legal training, according to executive search firm Stuart Spencer. (By contrast, 40 percent have an MBA.) But the airline industry is unusually lawyer-heavy in its executive ranks. When you add Continental's president, Jeffrey Smisek, to Steenland and Anderson, the six main network carriers currently feature three lawyers in leadership roles.

Moreover, since the late 1950s, when the budding business started to take off, at least a dozen lawyers have led airlines. Many enjoyed long and successful runs. (And some, like Anderson, have headed more than one carrier.) Among them are pioneers like Northwest's Donald Nyrop and U.S. Air's Edwin Colodny. Probably the best known is the cofounder and longtime leader of Southwest Airlines Co., Herb Kelleher, who was himself succeeded by GC James Parker. How much their legal training helped them in their new jobs is an open question, but alone it's rarely sufficient preparation for success.

Experts say that attorneys tend to do best as executives in heavily regulated industries like financial services, transportation, pharmaceuticals, and the media. Not coincidentally, that's where they seem to be most heavily represented. When laws and regulations are woven into the fabric of a business, lawyers are more likely to be involved in business decisions. That involvement, in turn, can create opportunities for an attorney to ascend the hierarchy.

That's certainly been true in the airline industry. From its beginnings in the 1920s, when early airlines were hauling the U.S. mail, the industry has been driven by laws and transactions, so airlines have always needed lawyers' hands on the yoke. By 1938 the industry had expanded sufficiently to warrant the legislation that created the Civil Aeronautics Board, which was empowered to supervise safety, fares, routes, and even schedules. It was no wonder, then, that lawyers who worked at the CAB had little trouble landing jobs at the airlines. And not just as lawyers. Four of the 12 lawyers who later led airlines worked first at the CAB: US Air's Colodny, Northwest's Nyrop, New York Air's Michael Levine, and Philip Bakes, president of Continental and later CEO of Eastern.

As the industry has grown, so has its dependence on myriad contracts: labor agreements, equipment leases, and partnerships between carriers, for example.

"The industry is so law-infected that the lawyer is very much part of the business decision-making process," says Levine, an attorney and former CEO of New York Air who is now a distinguished research scholar at New York University Law School.

The airline that has the longest tradition of lawyers at the helm is the one that will most likely vanish by year's end. Northwest has had four of the 12 lawyer-CEOs. Lawyers have been CEOs there for 43 of the past 54 years. The first was Don Nyrop, whose long reign spanned an era. He took over in 1954 and didn't step down as CEO until 1978, on the eve of deregulation. He inherited an enterprise in danger of failing, and patiently built a solid company that he ushered into the jet age. By all accounts, he was the frugal manager the company needed. The largest problem he left behind was one that has bedeviled many a lawyer and CEO since, especially in his industry: He had fractious relations with the labor unions.

Following an 11-year hiatus (and three nonlawyer CEOs), John Dasburg took over in 1990. Dasburg, who began a string of three lawyer-CEOs likely to be Northwest's last leaders, was the quintessential nonpracticing lawyer. He attended law school only after he earned an MBA, and he did so, he says, to learn tax law. The subsequent explosion of litigation made him especially glad he did, he hastens to add, but he always intended to pursue a career in business. Before his decade at Northwest, Dasburg was a partner at KPMG and a top executive at Marriott Corp. Where was his legal background most helpful? Labor contracts, Dasburg says. There were tense negotiations on his watch, too, and disruptions that included a pilots' strike. Having a CEO who fully understood contracts was a big plus, he says.

Dasburg's successor, Richard Anderson, began his career as a prosecutor in Houston. He wasn't lured to the airline business by what NYU's Levine calls "aviation fascination" (an affliction Levine says he caught at age 6). It was purely the need to enhance his paycheck. That and the serendipity of living near the then general counsel of Continental Airlines. That GC, Richard "Ben" Hirst, was a former trial lawyer himself, and, as the top lawyer of Continental, he liked to surround himself with good ones. Hirst was particularly glad to recruit Anderson in 1987 because Continental was slogging through a bankruptcy. It wasn't just Anderson's legal skills that attracted Hirst, however. More important was his intellectual curiosity. Anderson wasn't content to focus on narrow legal assignments, Hirst says. He wanted to know everything about the business.

In 1990 Hirst moved to Northwest, and Anderson soon followed. A year later Hirst hired Steenland, whose transactional experience helped round out his team. A partner at a Washington law firm that's now part of DLA Piper, Steenland's practice included hundreds of newspaper acquisitions (representing media entrepreneur Dean Singleton) as well as plenty of transportation and government relations matters. Again, what impressed Hirst most was his eagerness to learn the business. And he was obviously a fast learner. When Hirst became senior vice president for corporate affairs in 1994, Steenland replaced him as GC. (Hirst returned to the job last year, and will be GC of the merged company.)

The key to their climbs up the corporate ladder only started with success in the legal department. Steenland acknowledges that his legal background provided him with "a critical analysis skill set that I think is very helpful in carrying out CEO duties." But it's rare, and it would be risky, for a GC to go straight to the executive suite, he says. Usually a board will want to see how a potential CEO functions as an operations executive, or a finance executive, or both. In addition to serving as president, Steenland also served as chief corporate officer.

Anderson's trajectory included SVP of technical operations and airport affairs, and COO. "I had hangars and engine shops and 8,000 mechanics," he says of his first operations job, which was an important step in his development as a business leader. In 2001 Anderson was named CEO, and Steenland was tapped to be the carrier's president. When Anderson left to take an executive job at UnitedHealth Group Incorporated, in 2004, Steenland took over as CEO. Last year Delta reeled Anderson back into the business to succeed yet another lawyer, Gerald Grinstein.

Dasburg says he guided Anderson's career at Northwest and groomed him for the top spot. "It was not Richard's legal mind, it was his numeric mind that struck my interest," says Dasburg, now CEO of ASTAR Air Cargo, Inc. Anderson could see patterns in numbers that other people couldn't, which meant he was not only a gifted operations executive, says Dasburg, he could also handle the financial responsibilities of the CEO.

The wild card, however, is always leadership. In some ways legal training can impede an executive's development as a leader, says Anderson. Lawyers aren't trained to be team players, he notes. Quite the contrary: Law firm partners compete with each other to maximize their billings. Coaxing them to work together "is like herding cats," he says. But as CEO, "you have to be prepared to manage by consensus" and do what's best for the entire organization.

The Delta-Northwest merger drew on the executives' legal skills, but relied more heavily on their business acumen and leadership. And, in the end, after each side decided the linkup was in their company's strategic interests, the personal relationships of Anderson, Steenland, and Hirst helped make it happen.

Two legal pressure points were particularly tricky. First, the execs had hoped to get what's called in the business "a full prenup" before the signing-an agreement between the merged company and the two pilots unions, along with a seniority list agreed to by both. Failure to achieve these agreements has scuttled many mergers. They tried to get it done, but ran out of time. Northwest decided to sign the agreement without one, Hirst says, because they believed that Anderson, who will be the CEO of the merged company, would make a persuasive case to the pilots of each fleet, and treat them evenhandedly.

In turn, Anderson agreed to let Steenland take the lead in handling the regulatory review, even though Steenland would not be a member of the merged company's management (he will, however, have a seat on the board). Beyond the golden share and the personal relationship between the two, Steenland had demonstrated consummate skill in taking Northwest through probably the most successful restructuring of any airline to date, and he'd been instrumental in lobbying for federal legislation in 2004 and 2006 that protected the pensions of airline employees.

So far the results have been encouraging. In August the pilots overwhelmingly approved a new collective bargaining agreement, and agreed to submit the seniority list to arbitration. The lawyers say no previous merger had accomplished this feat between a signing and closing. Steenland and Anderson testified before numerous congressional and state hearings on the merger, and the criticism has been far more muted than initially anticipated. Their conversations with the Justice Department, they add, have convinced them the antitrust review will be completed in time for a closing this year.

NYU's Levine says the reputation of both executives is riding on how the merged company does. In general, he says, most of the industry's lawyer-CEOs have been quite successful, but the jury is still out on a few. "Steenland has been captain of the inflatable through some very rough rapids," he says. "We have to see if the boat ends up right-side-up or upside-down." As for Anderson: "He's made a huge bet on what Delta needs to be," observes Levine, who describes himself as a friend and admirer. "If it's the right bet, it will have been a great business decision."

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