However, just as the merger was approved in 1968 the world of air travel took off, which affected public appetite for riding the rails. The new super-company was then forced to contend with tight regulations that put the brakes on their ambitious plans. Unfortunately they went bankrupt two years later among rumours of in-fighting and conflicts over leadership. This led the government to take action, and President Nixon signed the Rail Passenger Service Act in 1970, creating a national railroad entity that would later become known as Amtrak.

In 1989 Japanese technology firm Sony managed to buy Columbia Pictures from Coca-Cola. At the time Columbia was starting to struggle with large debts while Sony was eager to develop a presence in the movie industry. Sony paid $3.4 billion (£1.9bn). Analysts felt this acquisition had potential, but they couldn’t have been more wrong. 

Sony’s chairman Norio Ohga (pictured) wanted to bring in fresh producers and had his eyes on Peter Guber and Jon Peters of the Guber-Peters Entertainment Company. But they had already signed a contract with rival studio Warner Bros. Sony then had to shell out a whopping $500 million (£335m) to settle a lawsuit with Warner Bros, who were not happy that Sony had gone after their producers. Columbia then released a series of film flops such as Blankman, Physical Evidence and She’s Out of Control. Ultimately Sony suffered an enormous loss on its investment in Columbia, taking a $2.7 billion (£1.8bn) write-off on the deal in 1994.

Trying to transform the reputation of a brand and take it outside of a successful niche is often a recipe for disaster. Iconic food brand Quaker Oats learned this the hard way when it acquired fruity juice drink brand Snapple for $1.4 billion (£938m) in 1994.

Not only did Quaker Oats overpay for Snapple, it then launched straight into a marketing campaign that aimed to encourage restaurants and supermarkets to stock Snapple. The problem was Snapple was firmly established as a ‘convenience’ drink designed to be quickly grabbed at corner stores and petrol stations. After this blunder, Quaker Oats found it tricky to recover and three years later it sold Snapple at a loss for just $300 million (£184m).

Keen to get its hands on iconic marques such as the Mini (1994 model pictured) and premium four-wheel drive model Land Rover, BMW quickly acquired Rover for $1.35 billion (£904m). However, the honeymoon period abruptly ended when Rover immediately started to experience heavy losses, partly due to BMW's lack of manufacturing experience and hands-off approach to running its new company. Further issues occured when the companies failed to resolve culture clash issues. Admitting defeat, BMW sold the Land Rover brand to Ford and offloaded many other Rover assets. However BMW did salvage something from this disaster – it kept hold of the beloved Mini marque, and it still produces them today.

In 1998 toy manufacturer Mattel acquired educational software company The Learning Company for $3.8 billion (£2.25bn). As the home of iconic brands such as Barbie, Hot Wheels and Fisher Price, Mattel’s aspiration was to bring its beloved big names into the emerging interactive games market. The deal went ahead despite analysts saying it was a bad move.

After just a few months, the merger created a high volume of product returns as stockists failed to sell products, which resulted in masses of unsold units clogging up warehouses. These failures led to a big departure of executive level staff members and resulted in an eye-watering 1999 calendar year loss of $206 million (£128m). However, Mattel acted fast and ditched The Learning Company less than a year after buying it and remains one of the biggest toy retailers to this day. 

However, Daimler-Benz’s luxury reputation didn’t align with Chrysler’s desire create affordable vehicles for drivers on a lower income. The merger floundered further when issues with language barriers and differences in management styles could not be reconciled and Chrysler was making losses. So finally, in 2007, Daimler-Benz sold Chrysler to Cerberus Capital Management for $7.4 billion (£3.8bn) in order to cut ties with the US company once and for all. 

Nowadays, Mark Cuban (pictured) is recognised as a successful billionaire, owner of basketball team the Dallas Mavericks and one of the ‘shark’ investors on TV’s Shark Tank. Back in the 1990s, however, he was merely known as the founder of broadcast.com, an online radio and TV site which enticed Yahoo! to part with $5.7 billion (£3.5bn) as it looked to expand its brand. 

Some failed mergers seem successful at first and only develop problems years down the line. This was the case when Deutsche Bank’s CEO Rolf Breuer (pictured) acquired Bankers Trust for $10.1 billion (£6.2bn) in 1999, which initially appeared to be a sound investment.

Bankers Trust was an organisation that specialises in offering loans to businesses such as then real estate developer Donald Trump (pictured in 1999 with his wife Melania) that other banks wouldn’t touch. It’d also received a lot of press attention for a recent corporate accounting fraud scandal, which had landed the firm with three felony charges and a $63 million (£39m) settlement to pay. But Deutsche Bank saw a bigger picture and felt this deal would finally allow it to compete with big Wall Street banks. At the time experts likened the risky deal to “going all in at the casino”, but after Deutsche Bank's purchase it quickly faded into the background. And 16 years later Deutsche Bank was finally forced to write off billions from the acquisition. 

Yahoo! also made another misstep in 1999 when it acquired a pioneering web-hosting service called GeoCities, which was popular in the 1990s and founded by David Bohnett (pictured). 

When Yahoo! purchased GeoCities, both brands were at the top of their game with Yahoo quickly becoming a leader in the tech industry and GeoCities hosting millions of live sites which were sorted into categories based on their contents. The problem was that Yahoo! didn’t seem to know what to do with GeoCities. So it did… nothing. Ten years passed with still no developments, which meant Yahoo!’s $3.6 billion (£2.2bn) investment had been worthless. So even though Geocities was still home to over 40 million pages it was shut down in the US in 2009. GeoCities Japan, however, was kept going until 2019.

The early 2000s were known in the business world as the years of the ‘dot-com bubble’ with online start-ups and internet companies all competing to make it big. That’s why when multinational mass media and entertainment conglomerate Time Warner purchased AOL for $165 billion (£104.5bn) in 2000 it was seen as a smart move by CEO Gerald M Levin (pictured). 

The vision behind the acquisition was that AOL would help to bring Time Warner into a new era of internet culture, chat rooms and instant messaging. But it ended up being a huge fail. The companies had vastly different structures and cultures that didn’t mesh well together. And when the dot-com bubble burst due to overvalued stocks, with many internet companies going bust, the entire industry suffered. Overall, AOL Time Warner reported a whopping $99 billion (£69.6bn) write-down in 2002, which led to the two brands parting ways in 2009. Many experts still consider this merger as one of the worst business deals of all time.

Another casualty of the ‘dot-com bubble’ was the 2000 deal between Spanish telecom company Terra Networks and search engine and web portal Lycos. This acquisition offers a great example of an established brand enticed by the vanity metrics of an exciting new brand. At the time, Lycos was flying high with 50 million users and 175 million page views per day, which swayed Terra Networks to part with $12.5 billion (£7.9bn) in a risky stock-for-stock deal.

The year 2003 saw telecommunications and networking conglomerate Cisco lose big when CEO John Chambers (pictured) acquired data networking hardware brand Linksys for $500 million (£317m). The deal initially seemed like a bright idea, with Cisco free to focus on selling to big companies while Linksys could take care of selling wireless routers to the small business and home demographic. But things didn’t quite work out. 

In 2005 online marketplace eBay had the brainwave to purchase telecommunications brand Skype for $2.6 billion (£1.35bn). The idea was that eBay sellers could use Skype to make calls, which would improve relationships between customers and sellers. 

However, eBay failed to take into account that email was a more effective, quicker and safer way for users to communicate. Over the next four years, eBay went through four different Skype management teams to try to get the merger to work, which resulted in a culture clash and toxic atmosphere. To try and recover from this failure, eBay eventually sold 65% of Skype for $1.9 billion (£1.4bn) in 2009. Skype was later bought by Microsoft for $8.5 billion (£5.2bn) in 2011, but in 2019 it announced it was closing the business arm of Skype and corporate users would have to transfer over to Microsoft's Teams by July 2021. Skype for personal use will remain active.

Remember Myspace? Often referred to as an early ancestor of Facebook, the original social networking site was purchased for $580 million (£301m) by News Corp, a mass media and publishing company owned by famous media proprietors the Murdoch family (pictured is patriarch Rupert Murdoch). 

At first, this was widely regarded as a way of ‘saving’ Myspace just as Facebook came onto the scene. But News Corp's first mistake was to try and rebrand Myspace as an entertainment hub, using it to push content from broadcasting company the Fox Corporation (also owned by the Murdoch family). Then when Myspace failed to reach its sales targets, News Corp initiated a mass firing of employees. In 2011 News Corp sold Myspace to Specific Media, an investment company owned by popstar-turned-entrepreneur Justin Timberlake (pictured), for a paltry $35 million (£21.5m). 

When two brands are from the same industry, yet each have something unique to bring to the table, this can be the perfect opportunity for a great merger. But when Sprint and Nextel joined forces in 2005 for $35 billion (£18.2bn), it was a huge letdown. Nextel was known as a more corporate business-focused brand while Sprint catered to consumers. And so combining their customer bases proved tricky.

It seems 2005 was quite the time for business deals destined to disappoint as it was also the year ageing retail giants Kmart and Sears came together. However, this idea did start out with some savvy, smart-thinking intentions. Noticing how the retail world was changing and realising it was losing out to competing retail outlets such as Target and Walmart, Kmart decided to purchase troubled department store chain Sears for $11 billion (£5.7bn), with both being led by Kmart Holding Corp. chairman Edward Lampert (pictured).

However, since coming together Sears has continued to haemorrhage money, more than $7 billion (£4.3bn) to be exact, and when Kmart experienced unprecedentedly awful Christmas sales figures in 2011 it had to resort to mass closures. Matters got worse in October 2018 when Sears filed for Chapter 11 bankruptcy, listing $6.9 billion (£5.65bn) in assets but $11.3 billion (£9.3bn) in liabilities. What followed was a wave of hundreds of store closures and the threat of liquidation. And while Lampert later received court approval to buy the struggling company for $5.2 billion (£4.3bn) in February 2019 through his hedge fund ESL Investments and keep it running, many have accused his business decisions as being what led to the decline in the first place. The deal meant that over 400 stores stayed open, however this was only temporary and soon more Sears stores started closing, and when the coronavirus pandemic hit that accelerated. As of 31 January 2021 there were only 36 stores left, and a further 13 closures have since been announced.

The famous name stores that could disappear in the next 10 years

Acquisitions often fail due to spiralling costs and unforeseen expenses, which can have a terrible effect on what initially seems like a profitable deal. This is exactly what happened when information technology and communications giant Toshiba purchased nuclear reactor manufacturer Westinghouse Electric for $5.4 billion (£3bn) in 2006. 

After paying $4.2 billion (£2.4bn) to Westinghouse in order to expand into the nuclear energy business, Toshiba failed to see a return when mounting construction costs and delays led to catastrophic financial losses. Toshiba was ultimately forced to write off $6.3 billion (£4.7bn) in losses and humiliatingly had to declare bankruptcy at Westinghouse, with the media referring to the deal as a ‘scandal’. Pictured is Westinghouse’s Co President Danny Roderick answering questions during an uncomfortable press conference at Toshiba’s headquarters in 2015. 

The 2006 deal cost a massive $13.4 billion (£7.6bn) but ended acrimoniously when Lucent CEO Patricia Russo and former Alcatel CEO Serge Tchuruk (both pictured) both resigned after failing to see eye to eye. The merged company then struggled on for years until it was snapped up by Nokia in 2016. 

An internationally-renowned bank acquiring one of the most respected financial advice brands in the world seems like a pretty safe bet. Unless that mergers occurs during one of the worst financial catastrophies in history, which is exactly what happened to Bank of America when it acquired wealth management and financial service provider Merrill Lynch for $50 billion (£25bn) in 2008. Bank of America’s CEO Ken Lewis (pictured) had wanted to work with Merrill Lynch for years but the timing couldn’t have been worse. The 2008 financial crisis erupted, destroying any chance of the merger’s success. Worse was to come when Merrill Lynch’s CEO John Thain departed mere months after the acquisition was announced. 

Bank of America shares fell 78% in the aftermath and the US federal government had to offer a ‘rescue package’ comprised of a $20 billion (£11bn) cash infusion and guarantees on $100 billion (£50bn) of troubled assets in order to save the bank. Pictured are Bank of America board members testifying at a Government Reform Committee hearing to determine what went wrong with the acquisition. 

Acquiring Merrill Lynch wasn’t the only terrible decision Bank of America made in 2008. That same year it also bought mortgage lender Countrywide Financial for $4.1 billion (£2bn). Pictured is Countrywide’s CEO at the time, Angelo Mozilo. Ordinarily this would have been an ideal way to grow the Bank of America brand, but in the wake of the 2008 mortgage and housing crisis it spelled disaster. 

Due to a lack of clear strategy from AOL, Bebo soon flopped after being overshadowed by rival social networking site Facebook. By 2010 AOL had given up on it and sold Bebo to investment consortium Criterion Capital Partners for between $2.5 million (£1.7m) and $10 million (£6.7m). Criterion Capital Partners brought original founder Michael Birch on board as a strategic adviser, but it didn't work. In 2013 Birch bought back the website he created with his wife for $1 million (£665k) in a bankruptcy auction. Birch sought to reinvent the social network, making a foray into video streaming software, a new arm of the business which was later acquired for $25 million (£18m) in June 2019 by Amazon-owned gaming platform Twitch. During that time the social networking site bebo.com went quiet, but now, seven years after Birch bought back his company, a completely new version of the Bebo website is set to launch later this month. A completely fresh start, as all content from its life as a 2000s social network has been lost, it remains to be seen if it become popular again.

Read more about Michael Birch and other rich people bankrolling entire villages, towns and cities

Cisco then took the drastic move of effectively "killing off" the range of pocket cameras (pictured). This left experts scratching their heads as to why Cisco would close such an expensive deal with Pure Digital in the first place, with many calling the failed acquisition "wasteful". 

Regarded as one of the most useless acquisitions in history, the relationship between Google and Motorola is subject to widespread industry analysis and attention. It all started when Google purchased Finnish telecommunications brand Motorola for a cool $12.5 billion (£7.7bn) in 2011 with the hopes of developing a range of high-end smartphones.

However, the reality did not match up to the vision. Motorola released a range of poor quality phones, such as the Nexus One, and reneged on a previous public promise to upgrade the phones of existing customers. This was not only detrimental to the Motorola brand but also tainted Google’s name in the eyes of the public. Google then took the strange step of releasing phones under its own Nexus brand, partnering with companies such as Samsung and LG, who are competitors of Motorola (pictured are Motorola and Google engineers and product designers at the launch). This course of action devalued the merger so much that Google eventually sold Motorola to Chinese technology brand Lenovo for $2.9 billion (£1.7bn) in 2014. 

Autonomy failed to fit into HP’s strategy and worse was to come when it was revealed that Autonomy had ‘cooked its books’ and been massively overvalued when HP had purchased it. This culminated in a nasty lawsuit and a $9 billion (£5.8bn) loss for HP. 

Game developing business Zygna is known for creating popular Facebook games such as Farmville. But in 2012 it had its eyes on another gaming company, OMGPOP, which had garnered a lot of attention due to its app Draw Something, a viral hit for smartphone users worldwide. 

But after acquiring OMGPOP for $210 million (£129m), Zynga, which was founded in 2007 by Mark Pincus (pictured), failed to see a return on investment. Draw Something became old news, with its active users dropping from 15 million to 10 million almost immediately after the merger. In a panic, Zynga began to take inspiration from other popular online games in order to boost profits, which led to allegations of copying.  The last straw came in the form of "sweeping layoffs" with hundreds of staff members losing their jobs. Zynga then effectively shut down OMGPOP a year after purchasing it.

The name Caterpillar is synonymous with heavy lifting equipment, with its machinery and engineering solutions used all over the world. Back in 2012 the company decided the best way to break into the lucrative Chinese coal market was to acquire ERA Mining Machinery Ltd for $677 million (£424m). 

While this initially seemed like a great deal, problems arose almost immediately. ERA was actually a holding company for Zhengzhou Siwei Mechanical & Electrical Equipment Manufacturing Co Ltd (commonly known as Siwei), a leading producer of hydraulic coal mine roof supports. Caterpillar had not sufficiently looked into this business before inking the deal, and so didn't know that Siwei had allegedly taken part in accounting misconduct for a number of years. Caterpillar ended up taking a $580 million (£364m) non-cash goodwill impairment payment, while Siwei later fired over 2,000 employees while investigating the issue. 

Yahoo! CEO Marissa Mayer (pictured) allegedly set unrealistic revenue goals and had to write down $482 million (£345m) in impairment costs from Tumblr in 2016 alone. Yahoo! also had to contend with a mass exodus of employees due to a culture clash and ended up having to write off total losses of $712 million (£510m). Verizon, which bought Yahoo! in 2015, eventially sold Tumblr for less than $3 million (£2.3m) in 2019.

Now read: Side-hustles that turned into multi-million dollar businesses