Kirk Kerkorian is struggling to end his long investment career on a high note.
Until last year, Mr Kerkorian, who turns 90 on June 6th, was set to be remembered as one of the builders of modern Las Vegas and for the handsome profits he reaped from a 14 per cent stake in Chrysler after the Detroit-based car maker fell into the arms of Germany's Daimler-Benz.
However, two of Mr Kerkorian's latest and boldest forays have not gone smoothly. An attempt to take the wheel of General Motors (GM) last year ended in humiliation. For a time, Tracinda - Mr Kerkorian's holding company named after his daughters Tracy and Linda - was GM's biggest individual shareholder.
Mr Kerkorian sold his shares last autumn after the car maker rejected his proposal for an alliance with the Renault-Nissan group. More recently, Mr Kerkorian struggled in his attempt to become a Chrysler shareholder for a second time.
DaimlerChrysler all but ignored Tracinda's $4.5 billion (€3.34 billion) offer, giving the nod instead to Cerberus Capital Management, the private-equity group.
The son of Armenian immigrants, Mr Kerkorian ferried aircraft across the Atlantic during the second World War. He used poker winnings to buy an aircraft in 1945, offering charter flights between Los Angeles and Las Vegas. Airlines have been among his favourite investments.
He sprang to prominence in the late 1960s by building Las Vegas's first mega-resort and, at the time, the world's biggest hotel. He also reaped handsome profits from twice buying and selling the Metro Goldwyn Mayer (MGM) film studio.
His investment in Chrysler paid off, with a $3 billion profit, but an attempt to take over Walt Disney in 1984 failed. Mr Kerkorian still controls MGM Mirage, the second-biggest publicly traded casino group.
He used the proceeds from the sale of his GM investment last year to raise his stake to 62 per cent. His future role at MGM has been thrown into question with last week's announcement he was seeking "strategic alternatives" for his stake, involving "financial restructuring transactions".
The news has sparked speculation that Mr Kerkorian is preparing to sell his holding to a private-equity group. At the same time, Tracinda has offered to buy two of MGM's prime properties, suggesting that its ageing owner still has ambitions in Las Vegas.
The extent of Mr Kerkorian's own involvement in this and other recent deals is hard to gauge. He relied heavily in his quest for GM and Chrysler on Jerry York, a former chief financial officer at Chrysler.
Mr Kerkorian has given only two interviews over the past decade - one to the Los Angeles Times shortly after he began his move on GM in mid-2005, the other to the Wall Street Journal last autumn when he sold the last of his 9.9 per cent stake.
The latter reported in December that Mr Kerkorian still drove himself to his nondescript Beverly Hills office in a Jeep Cherokee SUV. He has yet to start using a credit card.
Degeneration in his left eye had forced him to give up tennis, but he was hoping stem-cell surgery would be available to improve his vision. "I'm going to play again," he vowed. - (Financial Times service)
