NEW YORK ( TheStreet) -- Barnes & Noble ( BKS) is not known for its deal prowess, so plans to spin off its fast-growing and profitable Nook business should give shareholders pause.

The nation's largest in-store bookseller saw its shares open Thursday trading below $10 a share and within reach of all-time lows after the Nook announcement and a cut to its sales and earnings outlook. The share drop put into question the wisdom of the Nook digital books spin. The unit saw sales jump over 40% in this year's nine week holiday season, compared with 2010.

Nook tablets and digital content have been one of the only bright spots for Barnes & Noble, which has been hurt by declining sales of physical books for several years. In its business selling digital content and mobile e-reading devices, Nook's sales rose 43% from 2010, while Barnes & Noble brick-and-mortar rose just 2.5%.

On a dimming sales outlook and uncertain spin plans, Barnes & Noble's share plunge hit to two of its biggest shareholders, chairman Leonard Riggio and activist investor Ron Burkle and his Yucaipa Companies funds. Riggio, who bought Barnes & Noble in 1970, owns nearly 30% of the company's shares, while Yucaipa has a near 20% Barnes & Noble stake.

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Barnes & Noble cut its overall 2012 outlook for sales and earnings - leading to an earnings per share loss expectation as high as $1.40. Meanwhile, the company ascribed a glowing outlook to its Nook-fueled BN.com business, which it expects to grow as much as 50% in 2012, while its brick and mortar and Barnes & Noble College businesses achieve flat sales.

For more on Barnes & Noble here's a look at black-friday-2011-stock-short-squeezes and the reasons why Barnes & Noble can't act like Amazon.

With investors questioning the logic of Barnes & Noble's latest spin attempt, here's a look at the other deals that transformed the bookseller with a 100-year plus legacy, which did not always benefit shareholders.

4. Bertelsmann Takes a 50% Stake in barnesandnoble.com, an IPO Adventure Ensues.

Foreseeing the importance of the Web for retailers, Barnes & Noble launched barnesandnoble.com in 1997 to capture future online book sales after initial forays with partners CompuServe and AOL ( AOL) floundered.

By 1998, Barnes & Noble began preparing for an initial public offering of the site. That October, IPO plans were put on hold after German media conglomerate Bertelsmann paid $200 million and provided an additional $100 million capital commitment for a 50% stake in the Web books-selling arm of Barnes & Noble.

With Bertelsmann onboard, Barnes & Noble looked to take on rival online bookseller and Web sales pioneer Amazon, initiating a competitive relationship that's since gone on for over a decade.

Despite a more than 200% jump in sales, barnesandnoble.com losses escalated and operating costs exceeded sales in 1999. Nevertheless, barnesandnoble.com went ahead with an IPO in May 1999, raising $450 million in an exuberant tech hungry market, which bid up shares over 27% to $22.93 in their first day of trading.

Bertelsmann pulled the plug on the venture, selling its stake in barnesandnoble.com back to Barnes & Noble for $163.83 million in July 2003, after four consecutive lossmaking years. Barnes & Noble then bought the remaining publicly available shares of the venture for $3.04, an over 80% drop from their pre-IPO price.

With the Web site wholly owned once more, Barnes & Noble picked up an online books selling unit with $425 million in annual sales and a loss of $11.4 million at the time. Nevertheless, the deal paved the way for Barnes & Noble's later e-books and tablet devices push in Nook. The Nook unit, is housed within a now rebranded BN.com, Barnes & Noble's only fast-growing business, which is expected to eclipsed $1 billion in annual sales in 2011.

3. Barnes & Noble May Not Flunk on College Booksellers Deal.

After separating Barnes & Noble from its College Booksellers business in 1986 to help fund the purchase of B. Dalton Booksellers, the company bought the college textbooks unit back for $595 million in August 2009.

At the time the deal was cut, Barnes & Noble was just beginning to launch its digital books and e-reader business to take on Amazon's Kindle, after losing the battle for online book sales.

Barnes & Noble expanded into the stable-selling textbooks market and paved the way for a digital education push with the College Booksellers unit. Before the acquisition, the chain of 624 college bookstores carried the Barnes & Noble brand as a licensee - and generated $1.8 billion in revenue, compared with Barnes & Noble's consolidated $5.1 billion in sales. At the time, Barnes & Noble expected the deal to boost earnings per share by up to 35%, to a full year forecast of $1.40

College Booksellers' sales have fallen year-over-year in the last two quarters and 2011 sales fell below the $1.8 billion revenue mark it notched before Barnes & Noble bought the business. Nevertheless, management expects the unit to grow moderately in 2012 and be a big piece of its Nook push.

2. GameStop Spin Levels Up Against Barnes & Noble.

In October 1999, Barnes & Noble bought Babbage's Etc. a video games retailer partly owned by chairman Leonard Riggio for $215 million in cash.

The move was a push into growing video-game market as console makers Sony ( SNE), Microsoft ( MSFT) and Nintendo ( NTDOY) and software makers like Electronic Arts ( ERTS) drove gaming innovation. It was also expected to help barnesandnoble.com keep pace with rival Amazon by offering an expanded suite of PC and console games.

At the time of the deal, Babbage's Etc. operated 495 brick and mortar stores and an online games selling business valued at 5.1 times estimated 1999 EBITDA. To make the opportunistic purchase, Barnes & Noble drew on a $850 million line of credit.

Babbage's Etc. was then rebranded to the recognizable GameStop ( GME) brand, which saw stores and sales surge after the acquisition. By August 2001, GameStop nearly doubled its video-game selling stores and was preparing for an IPO after quarterly sales surged 63% to $206 million. With the IPO, Barnes & Noble expected to reduce its debt and recapitalize the gaming retailer.

After shelving the IPO until February 2002, GameStop shares made an impressive debut on the New York Stock Exchange, rising 12% to close at $20.10 - raising $325 million for Barnes & Noble. Since the IPO, the two companies have seen their fates diverge.

GameStop shares surged over 145% since its initial public offering - even after a post-recession slump and dimming sales outlook -- while Barnes & Noble has seen its shares cut by more than half. GameStop also has been profitable in every quarter as a public company, with sales and profits growing in 2010. Meanwhile, Barnes & Noble lost money in 2011, and is tied to a strategy of plowing cash into its Nook business to drive sales growth as its brick and mortar stores lag.

1. The Liberty Media Buyout That Never Happened.

After putting the company on the selling block in August 2010, Barnes & Noble spurned a May 2011 bid by John Malone run Liberty Media ( LMCA) to buy the bookstore for $1.02 billion, or $17 a share, a 20% premium to shares at the time.

Instead, Barnes & Noble settled on selling a 17% stake to Liberty Media for $17 a share or $204 million. Since the offer, Barnes & Noble shares have fallen over 40% as sales in its stores have slowed, diming its earnings outlook and potentially leading to Thursday's Nook spinoff proposal.

For Malone, who's taken opportunistic stakes in other companies like satellite radio giant Sirius XM ( SIRI) during the financial crisis, the Barnes & Noble partial investment has so far been a financial hit.

-- Written by Antoine Gara in New York

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