When Facebook puts itself up for sale in its initial public offering, now scheduled for next Friday, May 18, it is expected to be the biggest IPO in American history. Facebook has said it expects to raise around $12 billion from the offering, although other estimates peg the proceeds at closer to $10 billion. But a look back at the ten biggest previous IPOs shows that simply raising billions in the market is no guarantee of long-term success.

See also: The Landscape for the Facebook IPO

AT&T

The lower end of the estimates would put the offering at just about equivalent to the current record holder, that of AT&T Wireless. When AT&T spun off that part of its business in April 2000, it raised $10.6 billion, just as the highflying high-tech market of the 1990s was beginning its slide downward. AT&T priced its shares at $29.50, but by 2003, the stock was trading below $10. A merger with Cingular in 2004 was completed with a share price of around $15. (The current AT&T Wireless was created by AT&T in 2005 and is not part of the earlier company.)

[Photo credit: AP Photo/Eric Gay, file]

Kraft

The experience of the AT&T Wireless IPO scared off Verizon, which had been planning to spin off its own wireless subsidiary. But it didn’t prevent Philip Morris from spinning off Kraft in an IPO the following summer, on June 12, 2001. Philip Morris kept 88 percent of the company and sold the rest, a far cry from Facebook’s plan to sell about 64 percent of its stock.

Initially, the Kraft IPO was slightly less spectacular than the AT&T Wireless IPO, raising $8.68 billion. But for the long term, it was much more successful: Despite bouncing along like most American stocks in the past decade, Kraft is trading in the upper 30s now, above its IPO price of 31. Philip Morris (then known as Altria) sold its Kraft stock to the public in 2007, and Kraft became one of the 30 companies in the Dow Jones industrial average in September 2008. That’s a success story Facebook would be happy to emulate, although Kraft was obviously a well-established corporation at the time of its IPO, and it’s hard to compare a spinoff to a company selling itself.

[Photo credit: AP Photo/Morry Gash, file]

UPS

The third-largest was another success story involving a well-known American brand: United Parcel Service. UPS leapt out of the gate on November 10, 1999, with an IPO priced at 50 a share, which shot up to 70 before the day was over. All told, the offering raked in $5.47 billion. Although the stock has been up and down since then, it’s now trading near 80.

[Photo credit: AP Photo/David Duprey, file]

CIT

The fourth-largest IPO was another spinoff: CIT Group, a bank holding group that does primarily business lending. It had been around under various ownership schemes since 1908 and was wholly owned by Tyco when 100 percent of the company was spun off in 2002. The take at the time was $4.87 billion, at an offering price of $23, which slipped to $22 on the first day of trading.

After a strong first five years, in which the share price more than doubled, CIT collapsed with the rest of the financial sector in 2007, and eventually filed for bankruptcy in 2009. All of its common and preferred stock was canceled as part of the bankruptcy. Again, this is not the trail Facebook hopes to follow.

[Photo credit: AP Photo/Mark Lennihan, file]

Conoco

The fifth-largest IPO in American history was, at the time, the biggest, and took place in 1998 at the height of the dot-com stock hysteria. But it wasn’t a hot tech company; it was Conoco, the venerable oil giant. Like CIT, Conoco had been around a long time — since 1875 — and had been owned by various other entities. In 1998, parent company DuPont sold off around 30 percent of its stake in Conoco to the public for $4.4 billion.

The stock carried an offering price of 23, and rose to just over 25 on its first trading day. It’s been an unalloyed success since then: Conoco merged with Phillips Oil in 2002, and shares of the combined company currently trade at 54.

[Photo credit: AP Photo/David Zalubowski]

Citigroup

The sixth-largest IPO was another spinoff: Citigroup selling off Travelers Property Casualty in 2002. That one raised $4.27 billion. In seventh place is yet another: the short-lived Agere Systems, spun off from Lucent in 2002 at a cost to the public of $4.14 billion, then acquired by LSI Coroporation in 2007.

[Photo credit: AP Photo/Mark Lennihan]

Charter Communications

Finally, in eighth place, we arrive at the biggest IPO in which a fairly young standalone company was offering its stock to the public for the first time: Charter Communications, a cable TV and high speed internet company. Founded in 1993, Charter was owned by Microsoft co-founder Paul Allen when it had its IPO on November 8, 1999, raising $3.7 billion. From an offering price of 19, the share price rose to 27.75 later that month, but that would be its high-water mark. By 2002, the stock was selling for less than a dollar. Charter ended up filing for bankruptcy in 2009, then re-listed its stock later that year.

[Photo credit: AP Photo/Jeff Roberson, file]

Prudential

Ninth and tenth place belong to Goldman Sachs, which raised $3.66 billion in its 1999 IPO, and Prudential, which raised $3.48 billion in 2001. Both of those were century-old financial institutions that went public for structural reasons, and have little to do with Facebook.

Looking back over this list reveals just how audacious it is for Facebook to attempt to raise so much money. Nine of the ten largest American IPOs involved either spinoffs or long-established companies with iconic brands – or both.

Facebook is hoping its results are not like the one outlier on the list, Charter Communications, but rather more like Google, which launched its IPO in August 2004 for a relatively paltry $1.67 billion. But it’s now trading at more than six times its offering price of 85 – and no matter how many billions Facebook makes next week, it would love that kind of long-term performance.

[Photo credit: AP Photo/Douglas C. Pizac]