Italian arch dealmaker Stefano Pessina has finally found “the right shopkeeper” for Boots, four years after predicted there might be a long wait.

The Canadian branch of the Weston family, which once owned Selfridges, has bought the 177-year-old pharmacy and beauty chain for $8.9 billion.

After 20 years of steering what Pessina called “an iconic brand and a British institution” through various ownership structures and makeovers, with mixed success, he can finally close his medicine cabinet. “We are delighted to be passing on a thriving Boots,” he said.

It's been a “tortuous” process for Stefano Pessina and his wife Ornella Barra, who “through more than a thousand deals” once sought to dominate global pharmacy, says the .

Pessina, who took Boots private with the backing of investment firm KKR in 2007, kept a stake under different private-equity owners, and merged and de-merged the business with a US peer, Walgreens. A plan to re-float Boots was dropped in 2024.

But at least the Nottingham-based chain's future now seems secure. Pessina, 85, said he's now working “just 12” hours a day instead of the usual 18 he used to clock up. Yet clearly, “he hasn't lost his touch”, says . The entrepreneur and his latest private-equity partner, Sycamore, won't get the $10 billion they hoped for. But with sales driven up by a resurgence in beauty and the wild popularity of weight-loss jabs, the price fetched isn't “too far off”.

The Monaco-based power couple have been entwined romantically and commercially since the 1980s, when they combined their pharmaceutical businesses in their native Italy. They proved a winning double act: “Pessina as the methodical empire builder and Barra the hard-driving operator”. One former colleague recalls how “it was not uncommon for Barra to juggle closing a deal while packing Pessina's suitcase for their next trip”. He may be the strategist, but she is the engine room.

Stefano Pessina was born in 1941 in Pescara, and is a graduate of Milan's Polytechnic university. He started out in academia but, reportedly turned off by its left-wing politics, quit to join the market-research firm ACNielsen, says the Monaco Tribune.

In the mid-1970s, as Italy was struggling through a lengthy period of political and economic turmoil known as “the years of lead”, Pessina made the life-changing decision of attempting to salvage his family's failing wholesale pharmaceutical business. His “ability with numbers” came up trumps, says The Times. He repeated the trick for some of his father's business associates “in return for small stakes in their companies” and his deal-making career began.

There followed a whirlwind of takeover activity as Pessina's Alleanza Farmaceutica (shortly renamed Alleanza Salute Italia) became the country's undisputed leader in pharmaceutical distribution. France, Greece and Portugal followed. In 1997, Pessina broke new ground in Britain by acquiring Unichem, which had retail as well as wholesale and distribution operations. That gave him the scale to rise still higher, says The Guardian. Having “stalked” Boots for six years, Pessina flamboyantly invited its management for merger talks on his yacht off Sardinia in 2006. A year later, he teamed up with private-equity firm KKR to take the combined Alliance Boots private for around £11bn in what was then Europe's largest leveraged buyout.

The deal cast Pessina as an international predator. Yet from an investment standpoint it was hugely successful, says the FT. While most of the cheap credit-fuelled “mega-buyouts” of 2006-2007 crashed in flames, Boots was “a rare example of the alchemy coming good”. By 2012, when merger plans with the US drugstore giant Walgreens were announced, Pessina and his KKR partners had “almost tripled” their 2007 investment. That historic deal resulted in a truly global behemoth, with turnover close to $140bn by 2023.

Pessina, who is known for his “long, meditative periods of silence”, bestrode the world, says the Monaco Tribune. Times have changed. “Globalisation as we have known it is over,” he told the Italian daily La Stampa in 2024. It seems timely that he is now handing over the baton. Still, he will go down in business history as the “Italian alchemist” who turned deals into gold.

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