In this article, we discuss long-term returns of Carl Icahn’s 40 activist targets. You can skip our detailed analysis of Icahn’s activist targets and their historical performance and go directly to read Long-Term Returns of Carl Icahn’s 10 Activist Targets. 

He is one of Wall Street’s biggest stars and most successful investors. Carl Icahn is a force to reckon with as an American billionaire, financier, corporate raider, and private equity investor. He rose to prominence in the 1980s on investing in various public companies and demanding extreme corporate leadership and management changes to unlock shareholder value.

He has grown to become one of the biggest and most revered activist investors. His moves and calls in the market are often followed by investors who always rely on his activism to unlock significant value in undervalued or sleeping giants. “Icahn Lift” is the acronym that often refers to the shareholder value that comes about from Billionaire investor activism.

With a network of about $8.4 billion, Icahn dropped out of the New York University School of Medicine and started his long and fruitful career on Wall Street in 1961. He would go on to form Icahn & Co, a securities firm that would engage in various strategies to squeeze in value through risk arbitrage options trading or through other strategies.

It was in 1978 that the lone wolf of Wall Street started seizing control of positions in individual companies, including Viacom, Texaco, Philips Petroleum, and Western Union, among others, as part of his activism plays. In 1979 aggressive activism would earn Icahn $3 million on winning a seat on the board of kitchen stove maker Tappan and engineered its sale.

Driven by the philosophy of buying something that no one wants has etched his name as a contrarian investor. Icahn mostly focuses on identifying stocks with low price-to-earnings ratios and book values exceeding current valuation.

After purchasing a significant position in the company, he either calls for the election of the entire board or divestiture of assets to unlock shareholder value. Splitting up businesses’ and returning cash to shareholders to is one of the strategies he often deploys in the race to unlock shareholder value.

In 2015 he succeeded in convincing Apple Inc. (NASDAQ:AAPL), as part of his activism, to increase stock buybacks. The push came after the activist investor had a meeting with Apple CEO Tim Cook, after which he followed with a $150 billion buyback proposal while insisting the market was undervaluing Apple stock.

Activism has often put Icahn at crossroads with fellow high-profile investors. No one could ever forget his altercation with fellow activist investor Bill Ackman over the nutrition company Herbalife. As Ackman insisted the company was a fraud and poised to go to zero, he shorted the stock. Icahn, on the other hand, refuted the claims opting to buy large chunks of the stock.

As the founder and majority owner of Icahn Enterprises, Icahn mostly invests across seven operating segments, including Automotive, pharmaceutical, and home textile. He is also a big player in Tech and energy. In recent years, he has appeared to go slow, leaving his son Brett Icahn as Icahn Capital LP’s lead manager, an Icahn Enterprises subsidiary.

Contrary to perception, Icahn is not always on the winning side. Shares of Icahn Enterprises losing nearly a fifth of their value after Hindenburg Research announced the holding company was the target of its latest short underscores how things can also get nasty even for the lone wolf of Wall Street.

Hindenburg has also accused Icahn Enterprises of using money from new investors to pay out dividends to old ones terming such practices s Ponzi-like economic structures. Icahn, who has spent most of his life making such claims against other companies and investors, has resorted to waving off the claims terming the report self-serving.

In addition to the Hindenburg report, Icahn has also incurred a $9 billion loss in recent years on incorrectly predicting the financial markets will crash. He has admitted to learning his lesson on trying to time the markets and has since turned back to shaking up the companies he invests in.

Our Methodology

Amid the controversies and the losses, Icahn is still the go-to guy, given his solid stock-picking skills that have allowed him to amass significant wealth by betting on various stocks for decades. We have compiled a list of the billionaire investor, plays in the market, and how they have fared against the S&P 500 from the time of investment to when the famous investor exited the stocks. The stocks are ranked based on the chronological order of when the activist investor invested in the companies while also providing returns accrued over the investment period and compared with S&P gains over the same period.

40. Transocean Ltd. (NYSE:RIG)

Stock Return:  – 79.73%

S&P 500 Return: 44.47%

Investment date: 1/25/2013

Transocean Ltd. (NYSE:RIG) and its subsidiaries provide offshore contract drilling services for oil and gas wells worldwide. The company contracts its mobile offshore drilling rigs, related equipment, and work crews to drill gas and oil wells. Carl Icahn first invested in the company in early 2013, taking out a 3.2% stake in the offshore drilling contractor.

After that, the activist investor pushed for a shake-up of the board and a resumption of dividends that had been stopped the previous year. A fierce proxy battle would ensure that forced the company agreed to a $3 dividend against the $4 dividend that Icahn was pushing for. In addition, Icahn got seats on the board and continued to push for changes that he believed would unlock shareholder value. Part of the measures included reducing the number of board members. Nevertheless, in 2016 Icahn would trim his stakes in Transocean Ltd. (NYSE:RIG) by two thirds for tax planning purposes.

When he unloaded all his position at the end of 2016 his investment had yielded a loss of 79.73% against a 44.47% gain of the S&P 500 over the same period.

39. CVR Refining (NYSE:CVI)

Stock Return: -59.14%

S&P 500 Return: 75%

Investment date: 1/25/2013

CVR Refining was once a public company operating as a refiner and marketer of petroleum products. While being owned by CVR Partners LP, it was the subject of a fierce proxy war pitying billionaire investor Carl Icahn. As the biggest shareholder in 2013 with a 14.54% stake, Icahn sought to unlock value in the stock by demanding the company put itself up for sale.

Unknown to most people is that Icahn was plotting to acquire the company and take it private. He would later table a tender offer of $30 a share, which the company accepted. However, shareholders opposed the transaction and filed a class action lawsuit accusing the activist investor of manipulating the market price of CVR refining by issuing negative statements and threatening to delist the company.

In 2022 the parties settled with Icahn agreeing to pay the Unit holders $78.5 million without admitting any fault or liability.

While Icahn defended the transaction, it was one of his biggest mistakes as he incurred a loss of 59.14% on the investment, during which the S&P 500 gained 75%.

38. Herbalife Ltd. (NYSE:HLF)

Stock Return: 133.24%

S&P 500 Return: 173.93%

Investment date: 2/14/2013

Herbalife Ltd. (NYSE:HLF) is a health and wellness company that provides weight management products, targeted nutrition, energy sports, and fitness products. The company shot to the limelight in 2013 after Icahn acquired stakes to defend it against a short-selling campaign by another activist, Investor Bill Ackman.

Ackman had accused Herbalife Ltd. (NYSE:HLF) of being pyramid and opened a short position on the stock. Icahn grew his stakes in Herbalife to 15.5% leading to him getting seats on the board. He held stakes in the company until 2021 when he sold more than half of his holdings after Herbalife stock exploded to record highs amid solid earnings and growth prospects. He sold $600 million worth of stock back to the company.

Over the period Icahn held Herbalife, he is believed to have generated a 133.24% return from the investment compared to a 173.93% gain from the S&P 500.

37. Apple Inc. (NASDAQ:AAPL)

Stock Return: 55.84%

S&P 500 Return: 21.54%

Investment date: 8/13/2013

Apple Inc. (NASDAQ:AAPL) is a technology company that designs, manufactures, and sells personal computers, tablets, wearables, and accessories. In addition, the company offers various services, including Apple Music, cashless payment, and original content through Apple TV+. In 2013 Icahn confirmed the purchase of 27 million shares in the tech giant and increased his stake in the company in 2014 to 52 million shares, equal to a 0.9% stake.

While purchasing Apple Inc. (NASDAQ:AAPL), the activist investor reiterated that the company was highly undervalued and insisted it had the cash and borrowing capacity to do a massive buyback to jack up its stock price. The billionaire investor found himself at loggerheads as the company’s board asked shareholders to reject his proposal to spend most of their cash on buybacks and paying extra dividends. Icahn wanted the company to spend up to $150 billion on dividends and buybacks but watered the proposal to $50 billion.

When Icahn failed to get his way, he liquidated all his holdings in the company in 2016, the first year the company reported a sales decline in 13 years. Ultimately, he ended up with a 55.84% return outperforming the S&P 500, which was up 21.58% over the three years.

36. Nuance Communication

Stock Return: 5.24%

S&P 500 Return: 23.75%

Investment date: 8/29/2013

Nuance Communication was once a leader in conversational artificial intelligence and ambient intelligence across various industries, including healthcare, financial services, retail, and telecommunications. Icahn took the market by storm after confirming a 9.27% passive stake in the company in 2013.

With the investment, Icahn claimed he saw great potential in the company’s technology and market position, especially in healthcare. He would increase his stakes in the company to 13% and gain three seats on the board, one for himself, the other for his son, and the other for Icahn Enterprises CEO Keith Cozza. With the influence on the board, Icahn is believed to have pushed for the $19.7 billion deal that resulted in Microsoft acquiring Nuance.

Icahn gained 5.24% in Nuance Communication for the period he held the stock, compared to a 23.75% gain in the S&P 500.

35. Talisman Energy

Stock Return: -31.98%

S&P 500 Return: 26.25%

Investment date: 10/7/2013

Created from BP Canada, Talisman Energy was a Canadian independent oil and Gas Company with operations worldwide. It shot to the limelight in 2013 when activist investor Icahn bought 61 million shares for $277 million when the oil producer was underperforming by low commodity prices.

At the time, Icahn insisted on taking on the board to consider asset sales or restructuring to revitalize Talisman Energy’s fortunes. After gaining three seats on the board, Icahn would gain his way as he engineered a sale of the company to the Spanish company Repsol in 2015. He insisted that the $8.3 billion deal would create a stronger and more diversified company while unlocking shareholder value

Nevertheless, Icahn might have incurred a loss of 31.98% on the stock, a period in which the S&P 500 gained 26.25%.

34. VMware, Inc. (NYSE:VMW)

Stock Return: 3.98%

S&P 500 Return: – 7.37%

Investment date: 4/17/2018

VMware, Inc. (NYSE:VMW) is a leading provider of multi-cloud services for apps that enable digital innovation and enterprise control. The virtualization and cloud computing software vendor is the Dell Technologies subsidiary. Icahn first bought stakes in the company in 2014.

In 2018 he insisted that the company was worth $300 a share as he sought to scuttle Dell’s plan to go public while buying back the company shares. Dell had proposed a $21.7 billion to buy back VMware shares it did not own, a transaction that would allow it to go public without carrying out an IPO

After suing Dell over the proposed transaction, Icahn was forced to drop the lawsuit insisting it was unwinnable. When Icahn exited his position at VMware, Inc. (NYSE:VMW) in 2018, he gained 3.98% from the stock outperforming the S&P 500, down 7.37% over the same period.

33. Hologic, Inc. (NASDAQ:HOLX)

Stock Return: 63.98%

S&P 500 Return: 15.96%

Investment date: 11/21/2013

Hologic, Inc. (NASDAQ:HOLX) is a company that develops, manufactures, and supplies diagnostics products, medical imaging systems, and surgical products for women.

Icahn disclosed a 12.63%  stake in the company, prompting it to adopt a shareholder’s rights plan or poison pill as it sought to protect itself from a hostile takeover.

Icahn would gain two seats on Hologic, Inc. (NASDAQ:HOLX)’s board, from where he worked his way in unlocking value. At the time, the company struggled with cuts in hospital spending and a lack of reimbursement. Icahn engineered the reinstatement of former CEO Jack Cumming in the race to turn around the company’s fortunes.

Ultimately, Icahn’s activism would pay off as the stock rallied significantly, with Icahn generating a 63.98% return outperforming the S&P 500, which had only gained 15.96%.

32. eBay Inc. (NASDAQ:EBAY)

Stock Return: 6.72%

S&P 500 Return: 4.07%

Investment date: 1/22/2014

eBay Inc. (NASDAQ:EBAY) operates an online marketplace that connects buyers to sellers worldwide. The platform allows people to list, buy and sell various products. In 2014, the company found itself at crossroads as Carl Icahn acquired stakes and embarked on a long tussle with the board in a bid to revamp corporate governance practices and engineer a spinoff of a division.

In February of that year, he reiterated that lapses in corporate governance in the company were the most blatant he had ever seen. He took issue with director Marc Andreessen who had invested in seven startups that competed with eBay Inc. (NASDAQ:EBAY)’s PayPal. He called for an inspection of the company’s books.

Nevertheless, Icahn was forced to settle with eBay after failing to garner enough support for his proposed spinoff of the PayPal Unit. He was forced to withdraw his two nominees to the board. As he offloaded his stakes in the company in 2015, he had amassed a 6.72% gain above the 4.07% S&P 500 gain over the same period.

31. Family Dollar Stores

Stock Return: 29.26%

S&P 500 Return: 1.06%

Investment date: 6/6/2014

Family Dollar Stores was an American variety store chain that operated over 8,000 locations in all states except Alaska and Hawaii, mostly serving low-income customers. At its peak, it was the second-largest retailer.

In 2013, Icahn became Family Dollar Stores’s largest shareholder in the struggling retailer and started pushing for the company to sell itself.

With three seats on the board, he was the aggressor pushing for the company to sell itself to Dollar General even as he remained critical of the then-CEO.

Icahn would profit $200 million on the investment in 2016 as the company agreed to be acquired by Dollar Tree for $8.5 billion. His return amounted to a gain of 29.27% against a gain of 1.06% for the same period.

30. Seventy Seven Energy Inc.

Stock Return: -100%

S&P 500 Return: 7.06%

 Investment date: 7/9/2014

Seventy Seven Energy Inc. was a diversified oilfield Services Company that provided a wide range of well-site services and equipment in the US. The company offered upstream Services, including drilling, pressure pumping, and oilfield rental tools.

Icahn first got involved with the company in 2014 when it struggled with low commodity prices and high debt. After acquiring a 13.74% stake in the company, he pushed for cost-cutting measures, board changes, and asset sales to help improve the company’s fortunes.

Nevertheless, his effort did not have a significant impact, as Seventy Seven Energy Inc. filed for bankruptcy on July 7, 2016, after struggling with a $1.7 billion debt. With all the company’s outstanding shares canceled once it emerged from bankruptcy, Icahn incurred a 100% loss on the stock even as S&P 500 gained 7.06% in the same period.

29. Manitowoc Foodservice, Inc.

Stock Return: -6.45%

S&P 500 Return: 29.34%

Investment date: 12/29/2014

Manitowoc Foodservice, Inc. is a global leader in food service equipment and systems that builds and delivers the highest quality innovative product systems to enable healthy and safe food experiences. After acquiring a 7.7% stake, Icahn had the leeway to discuss the possibility of spearing the company’s crane and food service business into two separate entities.

In 2015, Manitowoc Foodservice, Inc. budged into Icahn activism, agreeing to separate its Cranes and Foodservice businesses. The investor also got his way by gaining a seat on the board. Over the four years that Icahn held stakes in the company; he amassed a loss of 6.45% as the S&P 500 gained 29.34%.

28. Xerox Holdings Corporation (NASDAQ:XRX)

Stock Return: -21.53%

S&P 500 Return: -115.63%

Investment date: 1/23/2015

Xerox Holdings Corporation (NASDAQ:XRX) is a workplace technology company that designs, develops, and sells document management systems and solutions. It offers workplace solutions, including desktop, monochrome color, and multifunction printers. Icahn first acquired stakes in the company in 2015 as part of his strategy of investing in undervalued and mismanaged companies.

After securing enough board seats, he is believed to have engineered the exit of several executives in the company, including Robert Zapf, and fired CEO JEFF Jacobson. His desire for leadership change is something familiar, as he always sees it as the only way to unlock value.

He remains the largest shareholder in Xerox Holdings Corporation (NASDAQ:XRX), with a 22% stake valued at over $573 million. Nevertheless, he has incurred a loss of 21.53% in the company underperforming the S&P 500, which has gained 115.63% over the same period.

27. Gannett Co., Inc. (NYSE:GCI)

Stock Return: 32.34%

S&P 500 Return: 7.08%

Investment date: 7/9/2015

Gannett Co., Inc. (NYSE:GCI) is a media and marketing solutions company that owns and operates over 260 daily newspapers and digital platforms. Icahn first got involved in the company in 2014 when it was considering splitting its publishing and broadcasting business into separate entities. He acquired a 6.6% stake in the company.

After gaining three seats on the board, he aggressively pushed for the split that he believed would unlock shareholder value. He succeeded in his push as Gannett Co., Inc. (NYSE:GCI) split its publishing assets that included USA Today, from broadcast and digital media business.

When Icahn liquidated his holdings in the company in 2016, he had generated a 32.34% return outperforming the S&P 500, which was down by about 7.08%.

26. Cheniere Energy, Inc. (NYSE:LNG)

Stock Return: 72.61%

S&P 500 Return: 100.71%

Investment date: 8/6/2015

Cheniere Energy, Inc. (NYSE:LNG) is a leading producer and exporter of natural gas in the United States. The full-service LNG provider also boasts procurement, transportation, liquefaction vessel chartering, and LNG delivery capabilities.

Icahn acquired stakes in Cheniere Energy, Inc. (NYSE:LNG) in 2015 when the company was struggling with a glut in supply that had triggered a significant drop in commodity prices. With about a 13% stake in the company and three seats on the board, Icahn pushed for cost-cutting measures, board changes, and asset sales in the race to unlock value.

Despite trimming his stakes in Cheniere Energy, Inc. (NYSE:LNG) in 2018 and 2019, Icahn reiterated his firm belief in the company’s long-term prospects. He would later increase his stakes in 2020 and 2021, buying about 12 million shares, impressed with the company’s turnaround and growth. He engineered a deal that saw the company agrees to purchase back around $350 million of his shares. 

Icahn has enjoyed a 72.61% return from his investment in Cheniere Energy, Inc. (NYSE:LNG), a period in which the S&P 500 has gained about 100.71%.

25. Freeport-McMoRan Inc. (NYSE:FCX)

Stock Return: 38.91%

S&P 500 Return: 37.41%

Investment date: 8/7/2015

Freeport-McMoRan Inc. (NYSE:FCX) is an exploration and development company that explores mineral properties focusing on copper, gold, and silver, among other metals. Icahn first acquired stakes in the company in Q3 of 2015, acquiring a 7.2% stake.

Icahn has been aggressive with his investments in the miner going by the number of transactions made. He consistently increases and trims his stake in Freeport-McMoRan Inc. (NYSE:FCX). Between 2020 and 2021, he increased his stakes by about 12 million, insisting that the company’s turnaround and growth was proceeding well, especially in the copper market.

Icahn investments in Freeport-McMoRan have earned a 38.91% return, better than the 37.41% S&P 500 gain.

24. Rentech Nitrogen Partners, L.P

Stock Return: -19.38%

S&P 500 Return: – 0.33%

Investment date: 8/9/2015

Rentech Nitrogen Partners, L.P was a pure-play nitrogen fertilizer company formed to own, operate and expand its business. The company used natural gas as its feedstock to produce anhydrous ammonia and UAN solution for sale to customers in the Mid Corn Belt

Icahn first acquired stakes in Rentech Nitrogen Partners, L.P in 2015 and gained seats on the board. As the company was struggling, he pushed for it to sell itself as one of the ways of unlocking shareholder value. The company would budge to pressure.

The company was acquired by CVR partners in 2015 for $533 million, excluding debt. Nevertheless, Icahn would incur a loss of 19.38% on his investment in the company, with the S&P 500 losing 0.33% over the same period.

23. American International Group, Inc. (NYSE:AIG)

Stock Return: -16.61%

S&P 500 Return: 27.86%

Investment date: 10/28/2015

American International Group, Inc. (NYSE:AIG) offers global insurance products for commercial, institutional, and individual customers. Icahn first disclosed a large stake in the company in 2015 while insisting that the company was too large despite years of dismantling.

After taking over, he engineered a proxy war, insisting American International Group, Inc. (NYSE:AIG) needed to break up. The smaller bit is the only way to unlock value. He was able to get board seats. After the company posted ugly-looking results in 2016, Icahn pushed further for a turnaround plan that resulted in pushing out the CEO

Icahn backed off from his demand to break up the insurance company following the sale of assets and hiring a new CEO. He offloaded all his stakes in the American International Group, Inc. (NYSE:AIG) in 2018, having incurred a 16.61% loss as the S&P 500 gained 27.86%.

22. Pep Boys

Stock Return: 26.64%

S&P 500 Return: – 8.57% 

Investment date: 12/4/2015

Pep Boys was one of the largest automotive aftermarket chains, with over 7,500 service bays in over 800 locations across the US. Icahn took an interest in the business in 2015, and, true to his strategy of engineering coups, he pushed for the sale of the business. Bridgestone Corp was the first to show interest in the auto parts company.

While it did table a $15.50 a share bid on the company, Icahn would come up on top with a $16.50 a share bid. Icahn’s bid came after increasing his stake in the company to 12.12% and insisting taking the company private and merging it with Auto Plus would be a perfect fit. After completing the acquisition, he merged the company with Auto Plus, resulting in a force to reckon with in the automotive industry.

Icahn’s investments in Pep Boys paid off, going by the 26.64% return against the 8.57% loss of the S&P 500 over the same period.

21. Conduent Incorporated (NASDAQ:CNDT)

Stock Return: -73%

S&P 500 Return: 98.31%

Investment date:1/9/2016

Conduent Incorporated (NASDAQ:CNDT) offers business process services with capabilities in transaction-intensive processing automation and analytics. It operates in three segments of commercial industries government service and transportation. In 2017, Icahn bought 19.8 million shares in the company, becoming one of the largest shareholders.

With the acquisition came three board seats that paved the way for Icahn to determine the company’s course. He was the force behind Clifford Skelton taking over as CEO. Conduent Incorporated (NASDAQ:CNDT) has not been a good investment as it has amassed a 73% loss for Icahn in a period in which the S&P 500 has returned 98.31%

Despite the intense activism, Icahn is at a loss, with his investment down 4.09%, underperforming the S&P 500 that, has gained 73.25% over the same period.

20. Welbilt Inc. (NYSE:WBT)

Stock Return: 45.34%

S&P 500 Return: 104.25%

Investment date: 3/11/2016

Welbilt Inc. (NYSE:WBT) is a company that provides the world’s top chefs and premier chain operators in the food and beverage sector with industry-leading equipment and solutions. Icahn started acquiring the company’s shares in 2016 and had amassed an 8% stake by 2021.

With his stakes in Welbilt Inc. (NYSE:WBT), Icahn was able to push for the potential sale of the company in a bid to unlock shareholder value. He endorsed a proposed sale of the food service equipment maker to Middleby. However, the deal never materialized as Ali Group tabled a much superior $3.3 billion offer representing a 15.5% premium.

Ali Group ended up acquiring the company, and Icahn enjoyed a 45.34% gain from his investment in the stock compared to a 104.25% gain from the S&P 500 at the time.

19. Hertz Global Holdings, Inc. (NASDAQ:HTZ)

Stock Return: -94.38%

S&P 500 Return: 42.06%

Investment date:7/11/2016

Hertz Global Holdings, Inc. (NASDAQ:HTZ) is a vehicle rental company that offers vehicle rental services under Hertz, Dollar, and Thrifty brands. Icahn first bought stakes in Hertz in 2016 and started his aggressive activism in the race to unlock value. He grew his stake in the company to about 55 million shares for a 39% stake making him the largest shareholder.

In 2014, Hertz Global Holdings, Inc. (NASDAQ:HTZ) agreed with Icahn on proposed board changes that resulted in the millionaire appointing his own people. However, in 2020, his investment went up in smoke as Hertz was one of the hardest hit amid the coronavirus pandemic. The company was forced to file for bankruptcy as the pandemic curtailed travel and created financial hardships.

The investor was forced to sell his equity at a loss after Hertz Global Holdings, Inc. (NASDAQ:HTZ) filed for bankruptcy protection. Icahn ended up with a 94.38% loss in Hertz, underperforming the S&P 500, which had gained 42.06% over the duration of his investment.

18. SandRidge Energy, Inc. (NYSE:SD)

Stock Return: -4.09%

S&P 500 Return: 73.25%

Investment date: 11/22/2017

SandRidge Energy, Inc. (NYSE:SD) is an independent oil and gas company that explores, develops, and acquires oil and gas properties. Icahn first bought stakes in the company in 2017, grew them to 13.6% by 2018, and started a fierce battle with the board as part of his activism. With the purchase, four of his people were appointed to the board.

He succeeded in blocking a proposed purchase of a rival oil and gas producer after stating the deal would not benefit shareholders but board members. He also accused the company of not disclosing its financial results. He supported the sale of North Park Basin assets in 2019 for $47 million, insisting it would help reduce debt and improve liquidity.

17. Newell Brands Inc. (NASDAQ:NWL)

Stock Return: -58.32%

S&P 500 Return: 63.49%

Investment date: 3/16/2018

Newell Brands Inc. (NASDAQ:NWL) designs manufactures, and distributes consumer and commercial products. It mostly deals in commercial cleaning, maintenance solutions, and closet and garage organization products. It also runs a home appliance segment.

From 2018, Icahn amassed a 9.3% stake in Newell Brands Inc. (NASDAQ:NWL), which put him in pole position to embark on an aggressive activism campaign. The company would cede to mounting pressure from the billionaire investor agreeing to appoint four people put forward by the investor to the board. Following the agreement, Icahn decided not to increase his stake or launch a proxy fight for an agreed period.

With Icahn in firm control, Newell Brands Inc. (NASDAQ:NWL) agreed to repurchase $257 million worth of shares held by Icahn Enterprise in 2022. Nevertheless, when Icahn bought stakes in the company, his holdings are down 58.32% compared to a 63.49% gain from the S&P 500.

16. Amtrust Financial Services, Inc. (NASDAQ:AFSI)  

Stock Return: 12.31%

S&P 500 Return: 0.65%

Investment date: 5/7/2018

Amtrust Financial Services, Inc. (NASDAQ:AFSI) is a financial service company that offers insurance protection, warranty programs, and risk management expertise to small businesses and professional and financial service firms. The company was at the center of a bitter standoff involving Carl Icahn in 2018 after announcing plans to go private as part of an ideal that involved the founding family, chief executive officer, and private equity funds.

Icahn strongly opposed the deal, insisting it was not in the shareholders’ best interest in value generation. The investor sued the company for trying to engineer a privatization deal at the wrong time and price.

Icahn, who owned a 9.38% stake, was joined by Czech-based Arca Capital, which held a 2.4% stake in the lawsuit. In the ensuing tussle, the group of investors seeking to take the company private agreed to sweeten the offer to $2.95 billion, which satisfied the opposing parties.

Once Amtrust Financial Services, Inc. (NASDAQ:AFSI) was sold, Icahn ended up with a 12.31% gain on his investment, outperforming the S&P 500 gain of 0.65% over the same period

15. The Cigna Group (NYSE:CI)

Stock Return: 13.76%

S&P 500 Return: 3.58%

Investment date: 8/1/2018

Together with its subsidiaries, The Cigna Group (NYSE:CI) offers insurance and other related products and services in the United States. It also provides pharmacy benefits, home delivery pharmacy, and specialty pharmacy distribution. Icahn first got involved with Cigna in 2018, grew his stakes to about 0.56%, and embarked on a fierce proxy fight with the board.

The bone of contention was the proposed plan to merge with Express Script. The board defended the move insisting it would create tremendous value for shareholders while accelerating transformation for healthcare. On the other hand, Icahn opposed the deal insisting that Cigna was overpaying for a company that faced existential risks.

Icahn would fail in his bid to block the $52 billion deal as he faced opposition from proxy advisory firms that supported the agreement, including Glass Lewis and Co and Institutional Shareholders Services. Icahn would exit his stake in the company seven months later for a 13.76% gain and outperforming the S&P 500, up 3.58%.

14. Tenneco Inc. (NYSE:TEN) 

Stock Return: -71.14%

S&P 500 Return: 40.73%

Investment date:10/1/2018

Tenneco Inc. (NYSE:TEN) is an automotive components original equipment manufacturer. It also operates as an aftermarket ride control and emissions products manufacturer. The company makes parts that help reduce pollution while optimizing engine performance. Icahn first got involved with the company in 2018 as part of his strategy of trying to unlock value in companies he believes are undervalued through activism.

Initially, he purchased 5.65 million shares and would later boost his holdings by 61.67% with the purchase of $3.48 million shares. He continued adding positions as the company’s share dropped. After acquiring stakes in the company Icahn was able to sell auto parts maker Federal-Mogul to Tenneco for $5.4 billion, unloading an investment he had held for nearly two decades

Icahn started trimming his position in Tenneco Inc. (NYSE:TEN) in 2021 and exited the company after incurring a 71.14% loss, during which the S&P 500 gained 40.73%.

13. Dell Technologies Inc. (NYSE:DELL)

Stock Return: 14.49%

S&P 500 Return: -9.64%

Investment date: 10/15/2018

Dell Technologies Inc. (NYSE:DELL) designs, develops, manufactures, and sells information technology infrastructure such as storage solutions, laptops, mobile software, and cloud solutions. In 2018, activist investor Carl Icahn declared a 9.3% stake in the technology company as he tried to oppose a proposed buyback of a stock that tracks VMware.

The activist investor would later sue Dell Technologies Inc. (NYSE:DELL) over claims they did not disclose financial results pertaining to plans to go public and buy back its tracking stock. The company had sought to buy back shares tied to interest in VMware. Icahn and other investors opposed the $21.7 billion deal that would take Dell public without holding an IPO.

Icahn would later agree to a revised deal that increased the tracking stock’s value to $120 from $109 a share. The investment in Dell Technologies Inc. (NYSE:DELL) would be lucrative as Icahn gained 14.49%, and the S&P 500 lost 9.64% over the investment period.

12. Energen Corporation (NYSE:EGN) 

Stock Return: 11.09%

S&P 500 Return: 3.94%

Investment date: 11/19/2018

Energen Corporation (NYSE:EGN) is an oil-focused exploration and production company. The company has primary operations in the Permian Basin of West Texas. In 2018 the company was the subject of takeover rumors, with various activist investors pushing for a sale. Corvex Management was one of the company’s pilling pressures for a sale. Elliot Management also joined Corvex in pushing for a sell

In May 2018, Corvex would sell its 2 million shares stake to Icahn. With Icahn in control, Energen budged into pressure and agreed to be acquired by Diamondback Energy for $84.95 a share. Icahn ended up with an 11.09% gain on his investment in the stock against an S&P 500 gain of 3.94% over the same period.

11. Cloudera Inc. (NYSE:CLDR)

Stock Return: 162.57%

S&P 500 Return: 48.68%

Investment date: 8/1/2019

Cloudera Inc. (NYSE:CLDR) is an American software company that provides enterprise data management and analytics platform. It boasts of a cloud-native platform built from the ground up to run on all major public cloud providers. In 2019, Icahn took a position in the company when it was under immense pressure from other emerging cloud players.

Icahn and his affiliates acquired more than 18% of Cloudera Inc. (NYSE:CLDR), giving them the right to appoint some people to the board. The activist investor successfully engineered a sale of the company for about $5.3 billion to private equity investors KKR and Clayton, Dubilier & Rice. The purchase price was a 24% premium to the company’s trading price.

Click to continue reading and see Long-Term Returns of Carl Icahn’s 10 Activist Targets.

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Disclosure: None. Long-Term Returns of Carl Icahn’s Activist Targets is originally published on Insider Monkey.