Andrés de la Cruz, Cleary Gottlieb Steen & Hamilton
Andrés de la Cruz, Cleary Gottlieb Steen & Hamilton (Carmen Natale)

Joe Frumkin and Eric Krautheimer, Sullivan & Cromwell

Sullivan & Cromwell has represented AT&T Inc. in mergers and acquisitions work for decades, developing a seamless team that came in handy when advising the telecommunications giant on 2016′s largest M&A deal.

Joe Frumkin and Eric Krautheimer led the team advising AT&T on its $108.7 billion acquisition of Time Warner Inc., constructing unique deal terms and doing it in lightning speed to help minimize the chance of leaks. The deal was negotiated in a week, including Frumkin’s work to line up $40 billion in financing in three days, as well as to secure a low breakup fee of $500 million.

“As a philosophical matter, AT&T has historically always done its big deals very quickly,” Frumkin says, noting his firm’s history with the client makes it well suited to keep pace with those goals.

The most interesting aspect of a deal that encompasses the rights to news and entertainment ranging from “Game of Thrones” to CNN may be its unique tax structure. It was structured as a tax-free “reorganization” even though shareholders received both stock and cash. Frumkin first used the concept in his representation of Enbridge Inc. in its $28 billion acquisition last year of Spectra Energy Corp. In the AT&T deal, Time Warner waived the right not to close if the tax status of the deal changes.

“It’s a structure that doesn’t condition the closing of the deal on being able to receive opinions that the deal is tax free to shareholders,” Frumkin says. “While it would be preferable for it to be tax free, particularly for Time Warner, [that] isn’t fundamental to the economics of the deal, so the thought is it isn’t appropriate to be a condition.”

Erica Berthou, Debevoise & Plimpton

It wasn’t the typical fund formation work for Erica Berthou, a Debevoise & Plimpton partner. She led a team that raised $6.5 billion for Blackstone’s GSO Capital Opportunities Fund III from roughly 200 investors—and did it in just about five months.

The condensed time frame for the fundraising effort meant that Berthou and her team had to fully devote themselves to the work of negotiating with investors. “We went all out,” she says.

The size and nature of the fundraising also presented challenges. Because GSO was raising capital for a closed-end fund, it required a long-term commitment from investors. And with about 200 investors eventually signing on, there were myriad viewpoints to consider and a high level of scrutiny.

Keeping her team focused and leading the way, Berthou helped GSO attract investors of different stripes, ranging from foreign sovereigns to U.S. public pension plans to family offices.

“When you have a fund of this size, there are a lot of investors—you want to make sure everyone is heard,” she says. “As a counselor, it’s not like an M&A deal where you can have very contentions negotiations. Here, we’re really building a partnership for the future and good ongoing relations are key. We are the face of our client.”

Bruce Bennett, Jones Day

Sometimes a feisty litigation battle serves as a precursor to a better deal for a client. Bruce Bennett of Jones Day can attest to that in the wake of his efforts to help a committee of noteholders reach a settlement in the Caesars Entertainment Operating Company bankruptcy that bumped up their recovery by more than $3 billion.

Bennett represented second priority noteholders in the bankruptcy, a group that included investment funds such as Appaloosa Management, Oaktree Capital Management, Centerbridge Partners and Tennenbaum Capital Partners. On the other side was Caesars and its private equity backers Apollo Global Management and TPG Capital.

He helped guide those noteholders through court battles and out-of-court negotiations during an intense, nearly two-year period starting in early 2014. Bennett’s goal—to help his lender clients get a better recovery than Apollo and TPG’s initial offer of 9 cents on the dollar—was far surpassed. The final Caesars reorganization plan offered the second priority noteholders 65.5 cents on the dollar.

“In a lot of ways, there was a litigation aspect to the project,” Bennett says. “But if you had asked me at any time, I would have told you, ‘This is going to end with a deal.’ The question was, what deal?”

Andrew Brownstein and Mark Gordon, Wachtell, Lipton, Rosen & Katz

When the level of antitrust scrutiny—and in turn the needed level of divestitures—is up in the air, valuing a deal can get pretty dicey. But with client The Valspar Corp. taking a deal-or-no-deal approach in seeking a buyer, Andrew Brownstein and Mark Gordon of Wachtell, Lipton, Rosen & Katz got creative. They structured a first-of-its-kind deal that featured a two-price, three-divestiture-tier model engineered to resolve an impasse over valuation.

Both Valspar and its acquirer, The Sherwin-Williams Co., agreed Valspar was worth $113 a share intact. But if certain pieces of the company had to be divested, what would the deal value be? Valspar didn’t think any significant divestitures would be required, and an attractive breakup fee wouldn’t be enough because by that point Valspar would have lost out on another deal it was giving up for the Sherwin-Williams tie-up. But the mutual trust between the two entities, Brownstein and Gordon say, allowed for a more creative model.

“It was, I think, a unique solution to a problem that is, in fact, not all that uncommon,” Brownstein says.

The parties agreed to pay $105 a share if divestitures of more than $650 million occurred, or $113 a share (more than $11 billion) if the divestitures were kept at a minimum. The team didn’t want to use a sliding scale between those numbers because it would provide incentives for either side to game the deal through pushing, or not, for divestitures.

“Getting the thresholds precisely right takes a lot of very detailed, asset-level analysis,” Gordon says. “It resulted in a package that just worked very well for both sides. And this is what you try to do as lawyers and problem solvers. It addressed both sides’ concerns very well.”

Matthew Hurd, Sullivan & Cromwell

Bayer’s $66 billion acquisition of Monsanto Co. turned out to be the largest all-cash M&A deal of all timebut it wasn’t supposed to be.

Sullivan & Cromwell’s Matthew Hurd initially worked to structure his client Bayer AG’s acquisition as a cash-and-stock transaction, but he had to act fast when a pre-announcement press leak caused Bayer’s stock price to drop.

Hurd and his team worked with lawyers on the other side to convert the deal to an all cash because Bayer had already lined up a commitment letter on a $57 billion line of credit. That made for the largest-ever acquisition financing. It was coupled with a low breakup fee Hurd helped negotiate.

There were many firsts in this deal. It also accounted for the biggest acquisition of an American company by a foreign buyer and the biggest M&A transaction by a German company.

Hurd took a Zen-like approach to the press leak, at least after the fact.

“If you can’t have secrecy, at least you can have preparedness,” Hurd says. “Secrecy and preparedness are what working on mergers and acquisitions is all about.”

This wasn’t the first time Hurd had worked on a deal where Monsanto was purchased. Nearly 20 years ago, he helped client Pharmacia purchase Monsanto, which was later spun off again.

George “Gar” Bason Jr.. Davis Polk & Wardwell

As a co-chairman of Davis Polk & Wardwell’s mergers and acquisition practice, George “Gar” Bason Jr. has done plenty of high-stake deals. But there was no exact precedent he could look to while representing Baker Hughes Inc. in its combination with General Electric Co.’s oil and gas unit.

With oil prices slumping, neither an all-cash or all-stock acquisition would work. Instead, the proposed deal calls for a partnership structure, in which GE Oil & Gas and Baker Hughes both contribute their assets to the “new” Baker Hughes, which will be a GE company. GE will take a 62.5 percent interest in the new partnership, while Baker Hughes shareholders will retain a 37.5 percent stake in the entity and also receive a one-time cash dividend.

In some ways, Bason says, the Baker Hughes-GE tie-up, which at press time was still subject to regulatory approval, was “fundamentally no different” from the exercise lawyers typically go through during a proposed transaction: Bason’s goal was to advance the interests of his client and its shareholders.

But there were unique challenges in protecting Baker Hughes shareholders, who would voluntarily become minority stakeholders in the new company.

“What was very different is, normally, you have lots of precedents to look to and you’re treading well-worn steps,” Bason says. “Here, it was writing on a clean slate.”

Andrés de la Cruz, Cleary Gottlieb Steen & Hamilton

A late-2015 administration change may have helped pave the way for Argentina to return to the world bond markets after a long-running court battle with certain creditors in the wake of a 2001 default. But the country also has to thank a Cleary Gottlieb Steen & Hamilton team led by Andrés de la Cruz, who helped push the Argentine government over the finish line to a $16.5 billion sovereign debt offering.

Led by de la Cruz, Cleary Gottlieb helped guide the Argentine government toward financing a settlement with most of the holdout bondholders who had been litigating against the country for years. He also led efforts to structure a trust that would allow Argentina to repay those bondholders while also being insulated from interference by other holdout creditors who didn’t accept the settlement.

“What we ended up doing was creating a trust to which the proceeds of the bond offering were attached,” de la Cruz says. “And that trust was basically shielded by attack from the holdouts.”

But there was one final challenge: getting Argentina’s disclosure documents up to date after a long absence from the bond markets. There, the firm’s long-standing representation of Argentina’s government paid off, says de la Cruz, because Cleary Gottlieb had a wealth of historical and institutional knowledge it could offer the new administration.

“Our contribution was very important, because I believe that without the institutional knowledge that we had … that would have delayed the process,” de la Cruz says.

Marc Kieselstein and Chad Husnick, Kirkland & Ellis

When Energy Future Holdings Corp. filed for bankruptcy in 2014, it was the biggest operating Chapter 11 in Delaware and the seventh-largest Chapter 11 case ever. The Texas-based generator, distributor, and retail electricity provider listed liabilities in excess of $49 billion and assets worth $36 billion spread across three separate units of the company.

While the company had tried to amend existing debt before its Chapter 11 filing, intercompany claims and loans across its three units ballooned, giving rise to competing creditors’ interests once bankruptcy proceedings began.

Kirkland & Ellis partners Marc Kieselstein and Chad Husnick led negotiations that reconciled multitudinous claims among the various creditors while finding a solution for the company to emerge from Chapter 11 unfettered.

Kieselstein and Husnick were also able to negotiate the separation of the TCEH unit from Energy Future without triggering a cash liability estimated at $6 billion.

Peter Thomas, Simpson Thacher & Bartlett

State-owned China National Chemical Corp., also known as ChemChina, agreed to purchase Swiss agrochemical and seed company Syngenta AG for $43 billion in the largest outbound Chinese investment ever in early 2016.

But this would be a tough sell to regulators, especially at a time of significant consolidation in the agrochemical industry.

“We knew going in that it was likely to attract very significant attention both in political circles in Washington as well as on the regulatory front,” Simpson Thacher & Bartlett’s Peter Thomas says.

National security concerns were raised by the Committee on Foreign Investment in the United States (CFIUS) over the implications of the massive agrochemical merger between the state-owned entity and Syngenta, a major supplier of products to the U.S. agricultural industry with facilities near U.S. military bases.

Thomas and his team at Simpson Thacher “quarterbacked” public affairs, government relations and regulatory strategies to fend off political headwinds from Capitol Hill.

Thomas worked to demonstrate to lawmakers and regulators that although ChemChina was a state-owned enterprise, it was indeed an independent and entrepreneurial company. He persuaded the company to identify its co-investors and their disclosure percentages, and showed that the transaction had a strong commercial rationale given ChemChina’s portfolio of chemical technology.

Thomas was also able to successfully negotiate the allocation of regulatory risk with Syngenta that contained noninclusion of reverse termination fees for ChemChina. In August, CFIUS signed off on the merger, removing one of the deal’s biggest impediments.

Stephen Arcano and Richard Grossman, Skadden, Arps, Slate, Meagher & Flom

Sometimes, the most important M&A work can be in making sure a deal doesn’t happen. For the Skadden, Arps, Slate, Meagher & Flom lawyers leading work for Norfolk Southern Corp., last year’s hostile takeover attempt was one of those times.

In the railroad industry, any merger must be approved by the federal Surface Transportation Board (STB). Skadden partners Stephen Arcano and Richard Grossman used this regulatory measure to thwart a $30 billion hostile takeover attempt launched by Canadian Pacific Railway Limited and its activist investor, Bill Ackman, on American railroad Norfolk Southern.

After rejecting three bids by Canadian Pacific, Arcano and Grossman counseled Norfolk to agree to discuss a potential deal only if Canadian Pacific obtained declaratory approval by the STB, as well as increased its offer price.

And the Canadian railroad did just that in early 2016, submitting a proposal to the STB for a voting structure that would have placed the Canadian Pacific CEO at the head of Norfolk, essentially “handing the keys over to Canadian Pacific management to run the railroad,” Grossman says.

The Justice Department, Department of Defense, and the U.S. Army all intervened before the STB on behalf of Norfolk, claiming this would compromise the independence of the American railroad. Before the STB could even vote, Canadian Pacific withdrew its proposal.

“[This] allowed Norfolk Southern’s management team to get on with implementing the value enhancing strategic plan that it had adopted and avoided the long distraction of an extended proxy fight or the regulatory limbo that would have resulted If Canadian Pacific and Norfolk Southern had entered into the proposed transaction,” Arcano says.

Amy Caton, Kramer Levin Naftalis & Frankel

Puerto Rico’s default is the largest municipal default in history. Over the years, the commonwealth and its agencies amassed close to $70 billion in debt. Amy Caton, a partner at Kramer Levin Naftalis & Frankel, has negotiated the only consensual deal with a restructuring support agreement which could form the basis for other debt negotiations.

“That, in and of itself, is a huge win because most people would like to cut their deals in Puerto Rico and move on,” Caton says.

Caton represents eight mutual funds holding more than $10 billion of that debt, making them the commonwealth’s largest creditors. They also held $3.2 billion of Puerto Rico Electric Power Authority (PREPA) bonds. In a deal that was held together at times “with chewing gum and paper clips,” Caton arranged for an $8 billion utility securitization that lowered PREPA’s debt service costs and provided increased protections for her clients.

“[My clients] were nervous about what it meant,” Caton says. But she reassured them that the securitization would ultimately provide them with more security and keep the politics out of PREPA that could result in increased utility rates.

The deal also contained forbearance agreements that provided PREPA with enough liquid capital to keep operating.

“Our clients, because they have such large investments in Puerto Rico, really do want to see Puerto Rico succeed at the end of the day,” Caton says.

Joshua Cammaker, Wachtell, Lipton, Rosen & Katz

Compared to some of 2016′s record-breaking deals, Lexmark International Inc.’s $3.6 billion sale to a Chinese private equity consortium coupled with a Chinese printer maker was small. But the deal was jam-packed with complexities and creative lawyering.

Wachtell, Lipton, Rosen & Katz’s Joshua Cammaker, who led Lexmark’s work on the deal, says it could be a template for future work involving Chinese acquirers.

“It was one of the more challenging deals I’ve worked on from a technical standpoint as well as from an overall cultural standpoint in terms of what works in the U.S. versus” in other countries, Cammaker says.

Given concerns over financing, antitrust and enforceability—since the acquirers were foreign private equity firms or lacked meaningful assets outside of China—Cammaker insisted on U.S.-style financing commitments from the Chinese lending banks and equity providers. He also extracted a “hell-or-high-water” commitment from the acquirers to obtain antitrust approval from the Committee on Foreign Investment in the United States, as well as other worldwide regulators.

Cammaker worked out other conditions, such as a $150 million letter of credit issued to Lexmark by the New York branch of the Bank of China to back up the consortium’s obligation to pay a reverse breakup fee. He also negotiated the exclusive use of the Delaware rapid arbitration program to settle any disputes, a waiver of sovereign immunity and the absence of a closing condition tied to approval by the Chinese printer company’s shareholders.

Running an auction helped put Lexmark in a position to negotiate these conditions, Cammaker says.

Correction, 3/28/17: An earlier version of this article misspelled the name Simpson Thacher & Bartlett and misstated the value of Canadian Pacific Railroad Limited’s hostile offer for Norfolk Southern Corp. as $30 million instead of $30 billion. We regret the errors.

Joe Frumkin and Eric Krautheimer, Sullivan & Cromwell

Sullivan & Cromwell has represented AT&T Inc. in mergers and acquisitions work for decades, developing a seamless team that came in handy when advising the telecommunications giant on 2016′s largest M&A deal.

Joe Frumkin and Eric Krautheimer led the team advising AT&T on its $108.7 billion acquisition of Time Warner Inc. , constructing unique deal terms and doing it in lightning speed to help minimize the chance of leaks. The deal was negotiated in a week, including Frumkin’s work to line up $40 billion in financing in three days, as well as to secure a low breakup fee of $500 million.

“As a philosophical matter, AT&T has historically always done its big deals very quickly,” Frumkin says, noting his firm’s history with the client makes it well suited to keep pace with those goals.

The most interesting aspect of a deal that encompasses the rights to news and entertainment ranging from “Game of Thrones” to CNN may be its unique tax structure. It was structured as a tax-free “reorganization” even though shareholders received both stock and cash. Frumkin first used the concept in his representation of Enbridge Inc. in its $28 billion acquisition last year of Spectra Energy Corp. In the AT&T deal, Time Warner waived the right not to close if the tax status of the deal changes.

“It’s a structure that doesn’t condition the closing of the deal on being able to receive opinions that the deal is tax free to shareholders,” Frumkin says. “While it would be preferable for it to be tax free, particularly for Time Warner, [that] isn’t fundamental to the economics of the deal, so the thought is it isn’t appropriate to be a condition.”

Erica Berthou, Debevoise & Plimpton

It wasn’t the typical fund formation work for Erica Berthou, a Debevoise & Plimpton partner. She led a team that raised $6.5 billion for Blackstone’s GSO Capital Opportunities Fund III from roughly 200 investors—and did it in just about five months.

The condensed time frame for the fundraising effort meant that Berthou and her team had to fully devote themselves to the work of negotiating with investors. “We went all out,” she says.

The size and nature of the fundraising also presented challenges. Because GSO was raising capital for a closed-end fund, it required a long-term commitment from investors. And with about 200 investors eventually signing on, there were myriad viewpoints to consider and a high level of scrutiny.

Keeping her team focused and leading the way, Berthou helped GSO attract investors of different stripes, ranging from foreign sovereigns to U.S. public pension plans to family offices.

“When you have a fund of this size, there are a lot of investors—you want to make sure everyone is heard,” she says. “As a counselor, it’s not like an M&A deal where you can have very contentions negotiations. Here, we’re really building a partnership for the future and good ongoing relations are key. We are the face of our client.”

Bruce Bennett, Jones Day

Sometimes a feisty litigation battle serves as a precursor to a better deal for a client. Bruce Bennett of Jones Day can attest to that in the wake of his efforts to help a committee of noteholders reach a settlement in the Caesars Entertainment Operating Company bankruptcy that bumped up their recovery by more than $3 billion.

Bennett represented second priority noteholders in the bankruptcy, a group that included investment funds such as Appaloosa Management, Oaktree Capital Management, Centerbridge Partners and Tennenbaum Capital Partners. On the other side was Caesars and its private equity backers Apollo Global Management and TPG Capital.

He helped guide those noteholders through court battles and out-of-court negotiations during an intense, nearly two-year period starting in early 2014. Bennett’s goal—to help his lender clients get a better recovery than Apollo and TPG’s initial offer of 9 cents on the dollar—was far surpassed. The final Caesars reorganization plan offered the second priority noteholders 65.5 cents on the dollar.

“In a lot of ways, there was a litigation aspect to the project,” Bennett says. “But if you had asked me at any time, I would have told you, ‘This is going to end with a deal.’ The question was, what deal?”

Andrew Brownstein and Mark Gordon, Wachtell, Lipton, Rosen & Katz

When the level of antitrust scrutiny—and in turn the needed level of divestitures—is up in the air, valuing a deal can get pretty dicey. But with client The Valspar Corp. taking a deal-or-no-deal approach in seeking a buyer, Andrew Brownstein and Mark Gordon of Wachtell, Lipton, Rosen & Katz got creative. They structured a first-of-its-kind deal that featured a two-price, three-divestiture-tier model engineered to resolve an impasse over valuation.

Both Valspar and its acquirer, The Sherwin-Williams Co. , agreed Valspar was worth $113 a share intact. But if certain pieces of the company had to be divested, what would the deal value be? Valspar didn’t think any significant divestitures would be required, and an attractive breakup fee wouldn’t be enough because by that point Valspar would have lost out on another deal it was giving up for the Sherwin-Williams tie-up. But the mutual trust between the two entities, Brownstein and Gordon say, allowed for a more creative model.

“It was, I think, a unique solution to a problem that is, in fact, not all that uncommon,” Brownstein says.

The parties agreed to pay $105 a share if divestitures of more than $650 million occurred, or $113 a share (more than $11 billion) if the divestitures were kept at a minimum. The team didn’t want to use a sliding scale between those numbers because it would provide incentives for either side to game the deal through pushing, or not, for divestitures.

“Getting the thresholds precisely right takes a lot of very detailed, asset-level analysis,” Gordon says. “It resulted in a package that just worked very well for both sides. And this is what you try to do as lawyers and problem solvers. It addressed both sides’ concerns very well.”

Matthew Hurd, Sullivan & Cromwell

Bayer’s $66 billion acquisition of Monsanto Co. turned out to be the largest all-cash M&A deal of all timebut it wasn’t supposed to be.

Sullivan & Cromwell ‘s Matthew Hurd initially worked to structure his client Bayer AG ‘s acquisition as a cash-and-stock transaction, but he had to act fast when a pre-announcement press leak caused Bayer’s stock price to drop.

Hurd and his team worked with lawyers on the other side to convert the deal to an all cash because Bayer had already lined up a commitment letter on a $57 billion line of credit. That made for the largest-ever acquisition financing. It was coupled with a low breakup fee Hurd helped negotiate.

There were many firsts in this deal. It also accounted for the biggest acquisition of an American company by a foreign buyer and the biggest M&A transaction by a German company.

Hurd took a Zen-like approach to the press leak, at least after the fact.

“If you can’t have secrecy, at least you can have preparedness,” Hurd says. “Secrecy and preparedness are what working on mergers and acquisitions is all about.”

This wasn’t the first time Hurd had worked on a deal where Monsanto was purchased. Nearly 20 years ago, he helped client Pharmacia purchase Monsanto, which was later spun off again.

George “Gar” Bason Jr.. Davis Polk & Wardwell

As a co-chairman of Davis Polk & Wardwell ‘s mergers and ac quisition practice, George “Gar” Bason Jr. has done plenty of high-stake deals. But there was no exact precedent he could look to while representing Baker Hughes Inc. in its combination with General Electric Co. ‘s oil and gas unit.

With oil prices slumping, neither an all-cash or all-stock acquisition would work. Instead, the proposed deal calls for a partnership structure, in which GE Oil & Gas and Baker Hughes both contribute their assets to the “new” Baker Hughes , which will be a GE company. GE will take a 62.5 percent interest in the new partnership, while Baker Hughes shareholders will retain a 37.5 percent stake in the entity and also receive a one-time cash dividend.

In some ways, Bason says, the Baker Hughes-GE tie-up, which at press time was still subject to regulatory approval, was “fundamentally no different” from the exercise lawyers typically go through during a proposed transaction: Bason’s goal was to advance the interests of his client and its shareholders.

But there were unique challenges in protecting Baker Hughes shareholders, who would voluntarily become minority stakeholders in the new company.

“What was very different is, normally, you have lots of precedents to look to and you’re treading well-worn steps,” Bason says. “Here, it was writing on a clean slate.”

Andrés de la Cruz, Cleary Gottlieb Steen & Hamilton

A late-2015 administration change may have helped pave the way for Argentina to return to the world bond markets after a long-running court battle with certain creditors in the wake of a 2001 default. But the country also has to thank a Cleary Gottlieb Steen & Hamilton team led by Andrés de la Cruz, who helped push the Argentine government over the finish line to a $16.5 billion sovereign debt offering.

Led by de la Cruz, Cleary Gottlieb helped guide the Argentine government toward financing a settlement with most of the holdout bondholders who had been litigating against the country for years. He also led efforts to structure a trust that would allow Argentina to repay those bondholders while also being insulated from interference by other holdout creditors who didn’t accept the settlement.

“What we ended up doing was creating a trust to which the proceeds of the bond offering were attached,” de la Cruz says. “And that trust was basically shielded by attack from the holdouts.”

But there was one final challenge: getting Argentina’s disclosure documents up to date after a long absence from the bond markets. There, the firm’s long-standing representation of Argentina’s government paid off, says de la Cruz, because Cleary Gottlieb had a wealth of historical and institutional knowledge it could offer the new administration.

“Our contribution was very important, because I believe that without the institutional knowledge that we had … that would have delayed the process,” de la Cruz says.

Marc Kieselstein and Chad Husnick, Kirkland & Ellis

When Energy Future Holdings Corp. filed for bankruptcy in 2014, it was the biggest operating Chapter 11 in Delaware and the seventh-largest Chapter 11 case ever. The Texas-based generator, distributor, and retail electricity provider listed liabilities in excess of $49 billion and assets worth $36 billion spread across three separate units of the company.

While the company had tried to amend existing debt before its Chapter 11 filing, intercompany claims and loans across its three units ballooned, giving rise to competing creditors’ interests once bankruptcy proceedings began.

Kirkland & Ellis partners Marc Kieselstein and Chad Husnick led negotiations that reconciled multitudinous claims among the various creditors while finding a solution for the company to emerge from Chapter 11 unfettered.

Kieselstein and Husnick were also able to negotiate the separation of the TCEH unit from Energy Future without triggering a cash liability estimated at $6 billion.

Peter Thomas, Simpson Thacher & Bartlett

State-owned China National Chemical Corp., also known as ChemChina, agreed to purchase Swiss agrochemical and seed company Syngenta AG for $43 billion in the largest outbound Chinese investment ever in early 2016.

But this would be a tough sell to regulators, especially at a time of significant consolidation in the agrochemical industry.

“We knew going in that it was likely to attract very significant attention both in political circles in Washington as well as on the regulatory front,” Simpson Thacher & Bartlett ‘s Peter Thomas says.

National security concerns were raised by the Committee on Foreign Investment in the United States (CFIUS) over the implications of the massive agrochemical merger between the state-owned entity and Syngenta, a major supplier of products to the U.S. agricultural industry with facilities near U.S. military bases.

Thomas and his team at Simpson Thacher “quarterbacked” public affairs, government relations and regulatory strategies to fend off political headwinds from Capitol Hill.

Thomas worked to demonstrate to lawmakers and regulators that although ChemChina was a state-owned enterprise, it was indeed an independent and entrepreneurial company. He persuaded the company to identify its co-investors and their disclosure percentages, and showed that the transaction had a strong commercial rationale given ChemChina’s portfolio of chemical technology.

Thomas was also able to successfully negotiate the allocation of regulatory risk with Syngenta that contained noninclusion of reverse termination fees for ChemChina. In August, CFIUS signed off on the merger, removing one of the deal’s biggest impediments.

Stephen Arcano and Richard Grossman, Skadden, Arps, Slate, Meagher & Flom

Sometimes, the most important M&A work can be in making sure a deal doesn’t happen. For the Skadden, Arps, Slate, Meagher & Flom lawyers leading work for Norfolk Southern Corp., last year’s hostile takeover attempt was one of those times.

In the railroad industry, any merger must be approved by the federal Surface Transportation Board (STB). Skadden partners Stephen Arcano and Richard Grossman used this regulatory measure to thwart a $30 billion hostile takeover attempt launched by Canadian Pacific Railway Limited and its activist investor, Bill Ackman, on American railroad Norfolk Southern.

After rejecting three bids by Canadian Pacific, Arcano and Grossman counseled Norfolk to agree to discuss a potential deal only if Canadian Pacific obtained declaratory approval by the STB, as well as increased its offer price.

And the Canadian railroad did just that in early 2016, submitting a proposal to the STB for a voting structure that would have placed the Canadian Pacific CEO at the head of Norfolk, essentially “handing the keys over to Canadian Pacific management to run the railroad,” Grossman says.

The Justice Department, Department of Defense, and the U.S. Army all intervened before the STB on behalf of Norfolk, claiming this would compromise the independence of the American railroad. Before the STB could even vote, Canadian Pacific withdrew its proposal.

“[This] allowed Norfolk Southern’s management team to get on with implementing the value enhancing strategic plan that it had adopted and avoided the long distraction of an extended proxy fight or the regulatory limbo that would have resulted If Canadian Pacific and Norfolk Southern had entered into the proposed transaction,” Arcano says.

Amy Caton, Kramer Levin Naftalis & Frankel

Puerto Rico’s default is the largest municipal default in history. Over the years, the commonwealth and its agencies amassed close to $70 billion in debt. Amy Caton, a partner at Kramer Levin Naftalis & Frankel , has negotiated the only consensual deal with a restructuring support agreement which could form the basis for other debt negotiations.

“That, in and of itself, is a huge win because most people would like to cut their deals in Puerto Rico and move on,” Caton says.

Caton represents eight mutual funds holding more than $10 billion of that debt, making them the commonwealth’s largest creditors. They also held $3.2 billion of Puerto Rico Electric Power Authority (PREPA) bonds. In a deal that was held together at times “with chewing gum and paper clips,” Caton arranged for an $8 billion utility securitization that lowered PREPA’s debt service costs and provided increased protections for her clients.

“[My clients] were nervous about what it meant,” Caton says. But she reassured them that the securitization would ultimately provide them with more security and keep the politics out of PREPA that could result in increased utility rates.

The deal also contained forbearance agreements that provided PREPA with enough liquid capital to keep operating.

“Our clients, because they have such large investments in Puerto Rico, really do want to see Puerto Rico succeed at the end of the day,” Caton says.

Joshua Cammaker, Wachtell, Lipton, Rosen & Katz

Compared to some of 2016′s record-breaking deals, Lexmark International Inc. ‘s $3.6 billion sale to a Chinese private equity consortium coupled with a Chinese printer maker was small. But the deal was jam-packed with complexities and creative lawyering.

Wachtell, Lipton, Rosen & Katz ‘s Joshua Cammaker, who led Lexmark’s work on the deal, says it could be a template for future work involving Chinese acquirers.

“It was one of the more challenging deals I’ve worked on from a technical standpoint as well as from an overall cultural standpoint in terms of what works in the U.S. versus” in other countries, Cammaker says.

Given concerns over financing, antitrust and enforceability—since the acquirers were foreign private equity firms or lacked meaningful assets outside of China—Cammaker insisted on U.S.-style financing commitments from the Chinese lending banks and equity providers. He also extracted a “hell-or-high-water” commitment from the acquirers to obtain antitrust approval from the Committee on Foreign Investment in the United States, as well as other worldwide regulators.

Cammaker worked out other conditions, such as a $150 million letter of credit issued to Lexmark by the New York branch of the Bank of China to back up the consortium’s obligation to pay a reverse breakup fee. He also negotiated the exclusive use of the Delaware rapid arbitration program to settle any disputes, a waiver of sovereign immunity and the absence of a closing condition tied to approval by the Chinese printer company’s shareholders.

Running an auction helped put Lexmark in a position to negotiate these conditions, Cammaker says.

Correction, 3/28/17: An earlier version of this article misspelled the name Simpson Thacher & Bartlett and misstated the value of Canadian Pacific Railroad Limited’s hostile offer for Norfolk Southern Corp. as $30 million instead of $30 billion. We regret the errors.