Betting and gaming group Entain's six years in London's FTSE 100 index have brought more highs and lows than a night at the casino. But the Ladbrokes owner is leaving the big league in better shape than when it joined. Entain's shares have fallen by two-fifths over the past year, reducing its market capitalisation to just over £3bn and ensuring its relegation to the mid-cap FTSE 250 come the index reshuffle that kicks in on September 21. It feels a long way from a 2021 peak when its stake in a US sportsbook helped draw a £16bn takeover offer from US rival DraftKings. Since then, Entain has been on its own acquisition spree. It has also doubled its net debt to £3.6bn, tussled with activist shareholders and reached a £585mn settlement with UK authorities over historical bribery allegations in Turkey.

In that time, it has also gone through four chief executives — a number that doesn't include the two interim periods served by current boss Stella David. But Entain has emerged from all this frenzied activity a more diversified group, with operations spanning lotteries, casino games, horseracing and other sports, gaming machines and bingo in about 30 jurisdictions, up from 20. Online gambling accounts for three-quarters of revenues, up from three-fifths, while the number of betting shops has more than halved to 2,300. Ebitda last year was up two-thirds from 2019 levels.

Having bulked up in some ways, Entain could also create value by judiciously slimming down in others. In June, David announced the sale of a 20 per cent stake in its Polish and Croatian business for up to £366mn as well as the intent to divest its remaining 48 per cent at some point, spurring speculation about other potential spin-offs. Gambling remains, to some extent, a gamble. The UK government has shown itself ready to raid the industry's pockets when strapped for cash; last year an increase in online gaming duties led Entain to book a £488mn impairment charge.

BetMGM, its US sportsbook joint venture, could be a major source of growth, but state and federal watchdogs continue to disagree on how prediction markets should be regulated, a question that may ultimately need to be settled by the Supreme Court. Still, a sum-of-the-parts valuation puts Entain at £12 per share, according to Berenberg analysts, more than double its current price.