The Irish fintech and the private equity giant tabled a 60,50 US Dollars per share bid that would finance with debt facilities in the region of 50 billion US Dollars.

Reuters and Bloomberg reported that US Private equity Advent International and Irish fintech Stripe called off the talks for acquiring PayPal Holdings for disagreements with the target’s board about the transaction value and the significant regulatory complexities. Stripe, Advent and PayPal declined to comment.

In July 2026, Wall Street Journal said that NYSE-listed PayPal asked Stripe and Advent to sweeten their 60.50 US Dollars per share bid for a 53 billion US Dollars enterprise value. The firms received financing facilities of 50 billion US Dollars from a pool of banks that JPMorgan and Morgan Stanley lead (see here a previous post by BeBeez). The proposal at the time offered a premium of around 28% compared with the share price prior to the rumours emerging, but PayPal’s board deemed it inadequate, both because it believed it undervalued the company’s long-term worth and because of the regulatory and financial complexities of the transaction.

Reuters quoted Bernstein analysts as reckoning that PayPal management would not have accepted a price that was not significantly higher than 70 US dollars per share, whilst it was not clear whether Stripe and Advent could and would go so far beyond the initial offer. Ultimately, the parties were unable to reach an agreement on the valuation. Reuters also added that Stripe and Advent approached PayPal in April 2026 for tabling a bid with Nasdaq-listed Block (fka Square) a firm that Jack Dorsey founded that later withdrew from the talks.

On 28 August, Friday, PayPal stocks plummeted by 12.71% and closed at 53,66 US Dollars (61,47 US Dollars from the previous trading day) and below the 60,50 US Dollars bid of Stripe and Advent.

PayPal Holdings listed on Nasdaq on 20 July 2015, after a spin off from eBay. The IPO price was of 38 US Dollars per share for a market capitalization in the region of 47 billion di US Dollars (press release). In 2021, PayPal market capitalization hit an above 360 billion peak. However, the share price has lost much of its value due to the slowdown in growth and increasing competition from Apple Pay, Google Pay and other fintech operators.

The deal was also sensitive for antitrust reasons. Stripe and PayPal are direct competitors in various areas of payment processing and, according to rumours that emerged in July 2026, the closing of the transaction could have required the sale of Braintree, the merchant payment processing platform of PayPal that is also one of the fastest-growing businesses within the group.

Enrique Lores is the ceo of PayPal and during the analysts conference call for 2Q26 results announcement he left the door open to extraordinary transactions, explaining that the firm would carefully appraise any strategic opportunity or alternative capable of creating greater value for shareholders.

The collapse of the negotiations therefore leaves it up to the management to demonstrate that PayPal is worth more on its own than Stripe and Advent were prepared to pay. The group continues to struggle, particularly in the branded checkout sector, where competitive pressure from Apple Pay, Google Pay and Shop Pay gradually eroded the dominant position it had built up over the years. PayPal is also trading at significantly lower multiples than the sector average: according to LSEG data that Reuters cited, after negotiations called off, the share was trading at a forward P/E of around 10.85 times, compared with a median of close to 15 times for its peers.

Patrick Collison and John Collison founded Stripe in 2010. The company decided to focus a significant portion of its investment capacity on artificial intelligence. On 19 August, Wednesday, whilst negotiations over PayPal were still ongoing, Stripe announced the acquisition of OpenRouter, a marketplace that enables businesses to route and optimise the use of over 400 artificial intelligence models from more than 80 providers (press release). Reuters said that the deal was worth little above 8 billion US Dollars, Financial Times reported a transaction value of 8 billion in cash and shares.

OpenRouter, born in 2023, manages above 10 trillion token per day for a community of more than 10 million developers and companies. Menlo Ventures, Andreessen Horowitz and CapitalG are some of its investors. The acquisition is Stripe’s largest deal to date and forms part of the group’s strategy to position itself as a financial infrastructure provider for the e-commerce sector and the artificial intelligence economy.Sequoia Capital, Andreessen Horowitz, General Catalyst, Founders Fund, Khosla Ventures, Tiger Global, and others invested in Stripe that since its birth attracted more than 9 billion di US Dollars while its value hit a 95 billion US Dollars peak in 2021.

However, in 2023, rising interest rates shrunk Stripe enterprise value to 50 billion for a 6.5 billion US Dollars round. The company invested such proceeds in providing its workers with cash and paying tax liabilities relating to share options. After it became structurally profitable again, the company subsequently avoided further capital increases and instead opted to enable employees and early investors to cash in their shares through tender offers. The strong growth in revenue and payment volumes boosted Stripe valuation to 65 billion US dollars in 2024, 91.5 billion in 2025 and 159 billion US Dollars in February 2026.