It’s been said business is war without bullets. With that in mind, today we examine the good, the bad, and the ugly of some of the largest mergers and hostile takeovers in U.S. business history.

The Good – Exxon Mobil

This merger ended up a perfect model for what a highly synergistic partnership should be. Today with a market cap of over $339 billion, ExxonMobil is the 7th largest company in the world and the largest of the big oil companies. The partnership was formed on November 30, 1999, when Exxon (formerly Standard Oil Company of New Jersey) and Mobil (formerly the Standard Oil Company of New York) merged.

When forming a company larger than the GDP of most nations there will inherently be hurdles and unhappy people along the way. One of the largest hurdles this merger faced was with the United States Federal Trade Commission. In order for the deal to go through, ExxonMobil had to agree to the largest divestiture in U.S. history in order to comply with its antitrust charges. Once this hurdle was cleared, under the terms of the agreement Mobil shareholders were to receive 1.32015 shares of Exxon stock for every Mobil share held. Formally, Exxon bought out Mobil. At the time the merger was highly criticized. But today, nearly twenty years later, ExxonMobil stands as one of the most respected companies in the world.

The Bad – AOL Time Warner

You can’t talk big U.S. mergers without mentioning the ill-fated AOL Time Warner disaster. In 1996, during a speech to the American Enterprise Institute, then Federal Reserve Chairman Alan Greenspan railed against the attitude of ‘irrational exuberance’ he saw emerging with the explosion in the bubble. Few companies would have been better served to heed that warning more than AOL and Time Warner.

Looking back it’s hard to understate how pervasive AOL’s presence was in the late 1990’s. At the height of the boom, in early 2000, AOL had amassed a then staggering 25 million online users and was seen as the undisputed king of the bright new field of online media. It was this position, and the seemingly unlimited growth potential of the internet, that allowed AOL the confidence to make the bid for the ‘old media’ company Time Warner. With Time Warner’s library of ebooks, magazines, television shows, movies, and music and AOL’s digital distribution platform, the pair seemed unbeatable. On January 10th, 2000 it was announced that AOL would acquire Time Warner for $162 billion with AOL shareholders owning 55% of the new company and Time Warner shareholders owning the rest. At the time, this deal too was the largest merger in business history. The resulting company saw a market capitalization of $352 billion.

But the marriage was short lived however. Shortly after the deal was finalized, the bubble burst, and a recession began. In the blink of an eye the advertising revenues that the brash young AOL relied upon were gone. In 2002, the company was forced to take a good-will write down and posted a $99 billion loss. This was also due in large part to the fact that faster broadband internet service providers had now replaced the slower dial-up providers AOL once dominated. As subscribers continued to flee AOL, the value of the company plummeted from $226 billion at its height, to just $20 billion. On December 9, 2009 Time Warner officially spun-off AOL into it’s own company and the two officially parted ways. Today, Time Warner’s market cap sits at just over $79 billion, while AOL was purchased in 2015 by Verizon, for $4.4 billion.

The Ugly – Nabisco RJR

Few mergers have set the business world ablaze like the 1988 leveraged buyout of Nabisco RJR by Kohlberg Kravis Roberts & Co. In October and November of 1988, the struggle for controlling power of one of the nation’s largest companies Nabisco RJR (R.J. Reynolds Tobacco Company) was underway. Tensions began to mount when CEO, F. Ross Johnson, revealed his intention to buyout the rest of the Nabisco RJR’s shareholders. On October 20, 1988, Johnson, in partnership with the Wall Street firm Shearson Lehman Hutton, announced his intentions to take the company private with a $17 billion leverage buyout bid, at $75 a share. This initial salvo setoff a bidding war that would see many of Wall Street’s top investment firms jump into the mix. Over the next month firms as diverse as Salomon Brothers, Forstmann Little, Shearson Lehman Hutton, Goldman Sachs, First Boston, Merrill Lynch, and even Morgan Stanley had participated in the bidding war. By the end of November, after more than a month of heavily volatile stock fluctuations, the company went to the firm Kohlberg, Kravis and Roberts for $24.88 billion ($109 a share – $81 in cash, $18 in preferred securities, and $10 worth of equity in the acquiring company). At the time, it was the largest merger in U.S. history. When the deal closed, Johnson received $53 million from the buyout. The entire saga was later recounted in the book, and film, Barbarians at the Gate.