Google’s wearOS has struggled to topple Apple’s watchOS, so in 2020, it acquired fitness tracker favorite Fitbit for $2.1 billion. How Google will use Fitbit’s technology is still unclear, but the deal opens a path for the tech giant to start producing its own company-branded smartwatch. Google is also absorbing the 29 million active users who currently wear Fitbit health-tracking devices. 

Apple’s 2014 deal to buy Beats is the most expensive acquisition in the company’s history, but one of the cheapest deals on this list. The tech giant has made dozens of acquisitions since the late ’80s, but few have topped the billion-dollar mark. For all its cash on hand, compared to the likes of Google and Microsoft, Apple has been positively frugal.

Nest was a Google shop from the get-go; former Apple exec Tony Fadell co-founded Nest in 2011 with backing from Google Ventures. Three years later, Google brought Nest in-house in a $3.2 billion deal. It’s been a bit of a rocky road, but after a 2018 re-org, Nest’s smart home lineup of thermostats, locks, and cameras are now the foundation of Google’s smart home lineup. Nest is also at the front line of Google’s smart home war with Amazon, which scooped up smart home security company Ring in 2018 for a paltry $1 billion.

Cisco has spent the last several years shifting from hardware to software and services. The enterprise tech giant’s $3.7 billion acquisition of AppDynamics in 2017 bought the company a market-leading stake in the application performance management (APM) and infrastructure monitoring space. Adding some drama to the deal, Cisco scooped up AppDynamics only a day before the company was set to go public for around $100 million.

This is the story of a precariously named media company called Oath. In 2015, Verizon began building its media arm with a $4.4 billion deal to buy AOL, giving it a media portfolio including The Huffington Post, TechCrunch, and a collection of other small blogs and video platforms.

Oath, which combined AOL and Yahoo’s assets, was born in 2017 after Verizon completed its $4.4 billion acquisition of Yahoo. Of course the original deal value was $4.8 billion, but Verizon dropped the purchase price by $350 million in the wake of Yahoo’s catastrophic string of data breach disclosures affecting more than 3 billion accounts over several years. The company then went through several rounds of layoffs and yet another re-brand, this time to Verizon Media Group. In late 2020, it sold HuffPo(Opens in a new window) to BuzzFeed, which resulted in more layoffs.

Adobe’s $4.75 billion acquisition(Opens in a new window) of marketing automation software company Marketo closed in October 2018. Marketo was founded in 2006, went public in 2013, and was acquired by Vista Equity Partners for $1.8 billion in 2016. The deal gave Adobe a suite of lead management, marketing, and revenue tools to incorporate into its Adobe Experience Cloud as it works to keep pace with companies like Salesforce.

There are quite a few Microsoft deals on this list. Some are good deals; many are not. The $6.3 billion deal to buy online ad network aQuantive in 2007 is one of the latter. One of the worst deals of the Steve Ballmer era (and there are several) was chalked up as a massive loss when Microsoft wrote down almost the entire value of the deal ($6.19 billion) in 2012.

Salesforce’s $6.5 billion acquisition(Opens in a new window) of MuleSoft, which closed in May 2018, gave the enterprise software giant a microservices play to integrate all of its cloud-based apps with MuleSoft’s software-as-a-service (SaaS) integration platform. Salesforce has made plenty of acquisitions in recent years, including spending $2.8 billion for Demandware in 2016 and scooping up Attic Labs, CloudCraze, and Datorama in addition to MuleSoft in 2018 alone. CEO Marc Benioff also became the latest tech billionaire to buy into the media world, acquiring Time magazine from the Meredith Corporation for $190 million.

In 2020, TurboTax maker Intuit announced it would absorb a competitor in the tax preparation sector by acquiring Credit Karma for $7.1 billion. Later that year, the US Justice Department said it would permit the merger, but only because Intuit agreed to divest Credit Karma’s tax business. That business went to Square, the mobile payments provider, which paid $50 million for it.

Aside from aQuantive, none of Microsoft’s deals looks quite so dreadful in retrospect as its doomed acquisition of Nokia. Steve Ballmer’s $7.2 billion goodbye present in 2013 saddled the company with Nokia’s handset business and mobile IP just before Satya Nadella took over as CEO (and had to take long walks with Nokia CEO Stephen Elop in the snow). By the time the deal closed in 2014, Ballmer was gone. A year later, Microsoft wrote off $7.6 billion from the Nokia deal and announced 7,800 job cuts as Elop left the company.

Microsoft’s $7.5 billion acquisition of GitHub, the largest host of open-source code in the world, solidified the company’s about-face on open source. Microsoft has big plans for how to integrate the popular code-sharing platform and developer community into its cloud ecosystem.

Under the terms of this $7.5 billion deal, announced in 2020, Microsoft takes control of ZeniMax Media, which includes Bethesda Games Studios, id Software, Arkane, MachineGames, Tango Gameworks, Alpha Dog, Roundhouse Studios, and ZeniMax Online Studios. It now owns and controls all The Elder Scrolls and Fallout games, as well as id Software’s entire library of IP (including Wolfenstein, Doom, and Quake). Add to that Dishonored, Prey, and The Evil Within.

Another entry, another Microsoft deal. The tech giant closed its $8.5 billion acquisition of Skype in 2011, and has since integrated the video chat service across its business and consumer app portfolio. The word “Skype” has even become a verb, though Zoom took a bite out of its market share in 2020.

Oracle’s $10.3 billion acquisition of HR and enterprise resource planning (ERP) software provider PeopleSoft is one of the most contentious acquisitions in tech M&A history. The 2004 deal marked the bitter end of several years of hostile takeover attempts and lawsuits until Larry Ellison ultimately got his prize and bought PeopleSoft into submission.

Qualcomm’s bid for NXP may have failed, but NXP was already a chip powerhouse thanks to its $11.8 billion deal(Opens in a new window) to buy auto chipmaker Freescale in 2015. The acquisition ensured that NXP chips live in everything from entertainment and security systems to almost every connected element of a vehicle.

Google’s biggest-ever acquisition also turned out to be quite the misfire. Google spent $12.5 billion to acquire Motorola Mobility in 2011, largely to scoop up its vast patent library. The deal closed in 2012. As for actually manufacturing Google-branded Motorola phones, that part never made Google any money. So just two years later, Google flipped Motorola Mobility to Lenovo for $2.9 billion, while holding on to those patents. As for why Google sold Motorola and why Lenovo bought it, check out this 2014 analysis from PCMag’s Lead Analyst Sascha Segan.

Alcatel-Lucent has gone through several iterations in the past dozen years. In 2006, Alcatel and Lucent agreed to merge(Opens in a new window) in a $13.4 billion deal to create a combined telecom equipment powerhouse. Over the next few years, Alcatel-Lucent acquired a few more parts, and sold and spun off several others until Nokia (the non-smartphone iteration of the company post-Microsoft sale) announced plans to acquire it in 2015.

Security company Symantec dropped $13.5 billion(Opens in a new window) in 2004 to buy data storage provider Veritas Software, which created the fourth largest software company at the time. It’s also worth noting that security software company VeriSign, which Symantec acquired in 2010 for $1.25 billion, previously bought domain name registration company Network Solutions for a whopping $21 billion(Opens in a new window) during the dotcom boom in 2000. If you go back far enough, tech acquisitions are like Russian nesting dolls. Inside one company are the remnants of several others.

Not a tech acquisition, you say? Amazon would beg to differ. Amazon’s blockbuster $13.7 billion deal to buy the nationwide chain of Whole Foods supermarkets gave the company an existing brick-and-mortar retail infrastructure to expand its online shopping operations. Amazon has since introduced things like Amazon Prime perks, 30-minute grocery pickups, and a slew of other cross-promotional efforts to turn Whole Foods locations into yet another extension of Amazon’s e-commerce empire.

Intel made a big move into AI and autonomous vehicles when it spent $15 billion on Israeli self-driving tech company MobileEye in 2017. MobileEye’s computer vision, machine learning, and mapping tech now powers or will underlie Intel driver-assisted and autonomous driving systems in car brands including Fiat-Chrysler and BMW, and Intel is also working with Alphabet’s Waymo self-driving car unit.

In 2019, Salesforce scooped up Tableau, which is arguably the biggest player in the business intelligence (BI) and data visualization space, to add to its growing business software empire. Salesforce’s $15.7 billion all-stock deal gave it a new dimension to its customer relationship management (CRM) portfolio as it acquires its way to an end-to-end software ecosystem for running an enterprise organization.

Walmart’s efforts to keep with with Amazon didn’t stop at Jet.com. In May 2018, the company announced a $16 billion deal to take a 77% stake in Indian e-commerce company Flipkart. The deal closed in August 2018(Opens in a new window) to expand Walmart’s fight with Amazon to another one of the world’s biggest markets.

Nokia’s $16.6 billion acquisition of Alcatel-Lucent was announced in 2015 and closed in 2016. The move positioned Nokia as one the top players in telecom networking technology and services. It set the stage for the emergence of 5G networks in 2019 and beyond, with Nokia as one of the few major suppliers of 5G equipment for telecom companies around the world, alongside Ericsson and Huawei.

Microsoft is spending $19 billion to buy Nuance, a Massachusetts-based company that supplies virtual assistant and speech-recognition technologies to hospitals, banks, and retail businesses.  By buying Nuance, Microsoft is aiming to expand its presence in the enterprise software market, including in the lucrative healthcare sector. “AI is technology’s most important priority, and healthcare is its most urgent application,” said Microsoft CEO Satya Nadella.

Facebook’s most expensive acquisition wasn’t Instagram ($1 billion) or Oculus ($2 billion), but its $22 billion deal(Opens in a new window) to buy messaging app WhatsApp. Originally valued at $16 billion in early 2014, the price tag ballooned to $22 billion by October 2014 when the deal closed due to the soaring value of Facebook stock at the time. As 2018’s high-profile departures of both WhatsApp and Instagram’s founders might suggest, the long-term health of Facebook’s acquisitions may be far shakier than initially thought, as lawmakers seem more amenable to break-up discussions.

Many years of shifting markets and bad decisions led to HP’s 2015 split into HP Inc. and HP Enterprise, but none has quite so dubious a distinction as HP’s $25 billion deal to buy computer manufacturer Compaq in 2001. Widely considered one of the worst tech mergers in history, shareholders objected to then-CEO Carly Fiorina’s move over overlapping product lines and low profit margins in a traditional PC business that many of its competitors were already exiting at the time. In the four years following the deal, the merged HP lost half its market value and Fiorina resigned in 2005.

HP made another doomed $11 billion deal(Opens in a new window) for UK software company Autonomy in 2011. That one led to a fraud lawsuit and indictment for Autonomy’s founder before HP ultimately sold off the last of Autonomy’s assets(Opens in a new window) to Micro Focus in 2016. We’ll leave this disastrous deal as a footnote to HP’s even more expensive misfire. While we’re at it, HP also spent $13.9 billion on Electronic Data Systems (EDS) in 2008. We could’ve given all three of these deals their own spot, but for the sake of brevity (or at least some semblance of it on this very long list), consider this your HP entry.

If at first you don’t succeed, try, try again. After years of failed deals and false starts, the US in 2020 officially went from four to three major carriers when T-Mobile snapped up Sprint. The No. 4 carrier is no more, while T-Mobile is under new leadership. John Legere stepped down as CEO in 2019; Mike Sievert is now at the helm.

Of all Microsoft’s expensive acquisitions on this list, its biggest one ever was the $26.2 billion deal to buy LinkedIn. By the time the deal closed in late 2016, Microsoft had already begun enacting plans to integrate the social network for professionals with Office 365 and its sales and business software offerings. Up to this point, Microsoft has let LinkedIn remain largely independent. But there are still plenty of ways Microsoft might cross-pollinate to make use of LinkedIn’s data and access to IT decision-makers who might be using Microsoft products. The move also brought LinkedIn founder Reid Hoffman into the fold as a Microsoft board member, and gave Nadella’s Microsoft a much stronger foothold in Silicon Valley.

In late 2020, Salesforce made its biggest acquisition to date: $27.7 billion for team messaging app Slack. The idea is to combine Slack with Salesforce’s Customer 360 CRM to “create the operating system for the new way to work.” And to compete with Microsoft Teams, of course.

Microsoft buying GitHub was expected to be the biggest software company acquisition of 2018. Then IBM blew it out of the water with its $34 billion all-cash acquisition of open-source powerhouse Red Hat. The enterprise software company has a broad portfolio of open-source software, including its Red Hat Enterprise Linux (RHEL) distribution, its JBoss enterprise app platform, OpenStack hybrid cloud platform, and its OpenShift container service that altogether generated almost $3 billion in revenue in 2017. The deal closed in 2019, with Red Hat becoming its own unit of the company operating under IBM Cloud.

In October 2020, AMD bought semiconductor company Xilinx for $35 billion to help the chipmaker compete against Intel and Nvidia in the data center market. Xilinx is a San Jose-based company best known for producing field programmable gate array (FPGA) chips, which are often used in the telecommunication, automotive, aerospace, and defense industry to power hardware. Unlike a general CPU processor, an FPGA doesn’t need software instructions to run. Instead, the chip can be programmed via hardware through reconfigurable integrated circuits, enabling lower latency.