#13: Albertsons' exit was thrown into question last week
Deal value at time of purchase: $17.4 billion in 2006
Inflation adjusted value: $20.5 billion today
Buyers: Cerberus Capital Management, SuperValu, CVS
Cerberus was joined by a couple of corporate players in its buyout of Albertsons. And, it would take about nine years to line the company up for its big IPO — which was set to take place a week ago. But it didn't happen. The company scheduled its initial public offering the same day Walmart issued guidance that hurt many retailers' shares, and the offering was pulled indefinitely. This is one PE deal that still hasn't found the exits yet.
#12: Investors in Freescale Semiconductor waited a while to eek out a return
Deal value at time of purchase: $17.6 billion in 2006
Inflation adjusted value: $20.8 billion in today's dollars
Buyers: Blackstone Group, Permira, the Carlyle Group & TPG Capital
The deal for Freescale Semiconductor, at the time, represented the biggest LBO in the tech sector. But it didn't go so great. The company filed for IPO in 2011 and posted solid returns on public markets and ultimately agreed to be bought out by NXP Technologies earlier this year. After all this, according to a Forbes report, PE profits were meager.
#11 (tie): Silver Lake's first deal to buy Dell cost it nearly $25 billion at the time
Deal value at time of purchase: $24.9 billion in 2013
Inflation adjusted value: $25.4 billion today
Buyers: Silver Lake, MSD Partners and Michael Dell
In 2013, Silver Lake and Michael Dell — who helped seed the private equity investor's very first fund — embarked upon what would eventually lead to the biggest LBO in private equity history: Dell-EMC. The first time around, however, it took about $25 billion to get the deal done.
#11 (tie): Kinder Morgan was a rare bright spot for private equity investors in the energy sector
Deal value at time of purchase: $21.6 billion in 2006
Inflation adjusted value: $25.4 billion now
Buyers: The Carlyle Group, Riverstone and Goldman Sachs private equity
#10: KKR's round-tripper on its Alliance Boots investment
Deal value at time of purchase: $24.8 billion in 2007
Inflation adjusted value: $28.4 billion now
The deal for the European pharmacy company proved to be enormously valuable to KKR; earlier this year a Wall Street Journal report stated the investor quadrupled its money on the investment. KKR finished selling the last portion of its stake in Alliance Boots last year.
#9: Blackstone's stay at the Hilton has turned a paper profit
Deal value at time of purchase: $26 billion in 2007
Inflation adjusted value: $29.8 billion today
Buyers: The Blackstone Group
Part of the reason Blackstone has grown to be the biggest asset manager of all private equity is owed to its success doing real estate transactions. Hilton Hotels certainly qualifies as this, and it seems as if the hotel chain is part of a broadening attempt by Steve Schwarzman's private equity firm to continue its push into property. The deal was a success on paper, but Blackstone Group is yet to sell out all of its stake.
#8: Private equity investors' dials have been stuck on Clear Channel a while now
Deal value at time of purchase: $25.7 billion in 2006
Inflation adjusted value: $30.3 billion now
Buyers: KKR, Bain Capital and Thomas H. Lee Partners
It's not clear if, how, or when the private equity investors behind Clear Channel will be able to make an exit. The company has undergone several major strategy shifts in the years since its LBO, including the division of US operations from international ones.
#7: Alltel's LBO was a quick flip for private equity
Deal value at time of purchase: $27 billion in 2007
Inflation adjusted value: $31 billion now
Buyers: Goldman Sachs' private equity division and TPG Capital
The big winners on private equity's 'biggest deals ever' roster tend to be the quick flips. And that's just what Goldman Sachs' PE team and TPG Capital did, flipping Alltel Wireless to Verizon in a 2008 sale that netted the investors a tidy profit.
#6: The bet on Caesars rolled a seven for private equity investors
Deal value at time of purchase: $27.4 billion in 2006
Inflation adjusted value: $32.4 billion
Buyers: Apollo Global Management and TPG Capital
Two seasoned private equity firms went out and gambled on Caesars in 2006 and they ultimately made a bad bet. Today, most of Apollo and TPG's investment in Caesars has been wiped out and the casino conglomerate continues to undergo a messy bankruptcy.
#4: When two PE investors teamed to take Hospital Corp. of America private, it was the biggest buyout ever (at the time)
Deal value at time of purchase: $32.7 billion in 2006
Inflation adjusted value: $38.6 billion today
Buyers: Bain Capital, KKR & Merrill Lynch
One of the more successful mega-buyouts, the private equity trio that bought out HCA in 2006 brought it back to public markets five years later. It proved to be a big winner for the investors.
#3: Blackstone has successfully exited most of its Equity Office Properties deal
Deal value at time of purchase: $38.9 billion in 2007
Inflation adjusted value: $44.6 billion today
Buyers: Blackstone Group
Most private equity firms have struggled to navigate their biggest deals ever; Blackstone's deals through its real estate-dedicated fund and one of its private equity funds in EOP proved to be a successful deal. Blackstone has sold more than half of the properties it had invested in through the 2007 deal.
#2: The mega-buyout of energy company TXU turned ugly years later
Deal value at time of purchase: $44.4 billion in 2007
Inflation adjusted value: $50.9 billion today
Buyers: Goldman Sachs' private equity division, KKR, TPG Capital
When TXU (at $45 billion, the biggest buyout ever at the time), went bust it would also wipe out equity from investors including Goldman Sachs’ private equity division and TPG Capital, more than seven years after the deal was announced.
#1: KKR's 1989 LBO of RJR Nabisco is an industry legend
Deal value at time of purchase: $31.1 billion in 1989
Inflation adjusted value: $59.6 billion now
Though the deal was a feather in budding PE genius Henry Kravis' hat at the time, it turned out that the KKR-RJR Nabisco buyout generated little to no value for the investor, and bogged down the returns of the fund that did the deal.