Bobby McAlpine, chairman of Alfred McAlpine in the boom time of motorway expansion and well-known figure on the Turf – obituary

Bobby McAlpine, who has died aged 89, was an affable chairman of his family construction group and a familiar figure on the Turf as a steward, racecourse administrator and owner-breeder of several top-class racehorses.

A talented and highly competitive all-round sportsman, McAlpine was also a dedicated bon viveur. “He liked the best of everything,” said his great friend, the leading flat-racing trainer Barry Hills. “You couldn’t give him enough. If you trained him as a racehorse you’d run him every day.”

Hills trained several horses bred by McAlpine, including the standout Cormorant Wood, a big, rangy filly whose easy win in the Sun Chariot Stakes at Newmarket in October 1983 prompted McAlpine, as he recalled, “to go for the big one”, the Group 1 Champion Stakes a fortnight later.

She started that race at odds of 18-1 and in a near gale-force wind her jockey Steve Cauthen rode her from last to first in the final three furlongs, squeezing through the tightly bunched field in a burst of acceleration that Timeform recorded “had to be seen to be believed”.

Robert James McAlpine was born on May 6 1932, the elder of two sons of Jimmie McAlpine from the first of his five marriages. Jimmie’s father Alfred McAlpine, a younger son of Sir Robert (“Concrete Bob”) McAlpine, had run the north-western operations of the company started by his father in the 19th century.

In 1940 he established his own separate company, Sir Alfred McAlpine & Son, with a non-compete agreement to confine its work to the North Midlands, North Wales and the North West of England.

Bobby’s early childhood was spent in a series of large houses on the Welsh side of the border with Cheshire – which would later qualify him to play squash for Wales. He first discovered his love of champagne at an aunt’s wedding, when he pretended to several well-meaning guests that he had been promised a glass but never received it. A very tipsy young Bobby was eventually scooped up and taken back to the nursery – it would be a while before he was allowed his favourite drink again.

His parents divorced at the start of the Second World War, when he was sent away to a prep school that had been evacuated to Llanfyllin. He captained the cricket XI in his last summer in 1945 and later at Harrow played in the first rackets pair for three years and captained the school squash team.

In 1950, aged 18, he began work at Alfred McAlpine’s Wolverhampton office, learning the ropes on the construction site of Walsall Power Station, while playing squash for Wolverhampton and Staffordshire.

He moved to the main office at Hooton, on the Wirral, as a director soon after marrying in 1956 and setting up home at Lower Carden Hall, near Malpas.

In the winter he continued to shoot as many days as he could and in the summer played cricket for several clubs, including Marchwiel, where his grandfather had lived, one of the finest private grounds in the country.

Bobby McAlpine’s father had captained Denbighshire in the Minor Counties league before the war, playing as an opening bowler and hard-hitting middle-order batsman. By his own estimation, Bobby was a “rather stodgy” opening bat but improved considerably after a net session with Gubby Allen, one of several famous cricketers who played at Marchwiel.

The 1960s and early 1970s were boom times for Alfred McAlpine plc, which had gone public in 1958 and was responsible for a fifth of the country’s entire roadbuilding programme during this time, including long sections of the M6 motorway.

Bobby served as deputy chairman and later chairman after his father’s retirement in 1985. However, as the civil engineering contracts began to dry up in the 1980s it became a struggle to maintain the family’s presence in the business, which effectively ended with Bobby’s own retirement in 1992, after which he devoted himself to other businesses (including co-founding the wine merchant Haynes Hanson & Clark) and sporting pursuits.

A long-standing member of the Jockey Club and director of Aintree and Bangor racecourses, he was chairman of Chester from 1988 to 2007, and stewarded at Wolverhampton, Bangor, Chester, Haydock, Aintree and Newmarket.

His interest in racing had been fired as a boy when his uncle told him about winning the Grand National in 1921 with his horse Shaun Spadah. He was still in his twenties when, in a moment of recklessness after playing cricket with Ian Lomax, he agreed to buy a four-year-old gelding from Ireland called Marnrack, to be trained by Lomax’s wife Rosemary.

Marnrack won enough races to get McAlpine hooked: “The excitement,” he wrote, “of seeing a horse in one’s own colours run so well can only be realised by those who have gone through the same experience.”

Rosemary Lomax was a fine judge of horses and later advised McAlpine to buy the colt Precipice Wood as a yearling; he went on to win the King George V Stakes in 1969 (the first time a woman had trained a Royal Ascot winner) and the Ascot Gold Cup in 1970, beating the 1969 Derby winner Blakeney.

It would be more than decade before McAlpine had his next Group 1 winner, Cormorant Wood, and this time he had the added thrill of having bred her. Her last race as a three-year-old was the Arlington Million in America, where she entered the straight full of running but failed to stay the slight extra distance and finished sixth. McAlpine and his entourage had flown over by Concorde and his travel expenses – including a large bill for flying the horse over – wiped out a lot of her earlier winnings.

The next year she became the first filly to win the Lockinge Stakes at Newbury and in her last race romped home in the Benson & Hedges Cup at York, with Sadler’s Wells and Tolomeo, her victor in the Arlington Million, well behind.

Her half-brother River Ceiriog, also bred by McAlpine, later won the Supreme Novices’ Hurdle at Cheltenham in 1986 at odds of 40-1. Thinking he had no chance, his trainer Nicky Henderson had been reluctant to run him but bowed to pressure from “Mr Bobby”.

When, before the race, the commentator Peter O’Sullevan asked how to pronounce the horse’s name, Henderson replied: “Don’t worry, you won’t have to mention it!” River Ceiriog won by 15 lengths, the easiest winner McAlpine ever had – and fortunately he had ignored his trainer’s advice not to back it.

River Ceiriog and Precipice Wood were among several of McAlpine’s horses to derive their names from Llanarmon, the family shooting estate in North Wales. As grouse numbers declined in the 1980s, McAlpine and his keeper set about transforming the pheasant shoot there, making much better use of the hilly terrain, with the result that The Field included it in its list of Britain’s 50 finest sporting estates; McAlpine himself was ranked at No 54 in the 100 top shots of all time.

Clubs were another big part of McAlpine’s life, his memberships including several rackets, cricket and golf clubs – where he demonstrated a marked preference for winning over losing – as well as White’s, the Turf Club, Annabel’s, Mark’s Club and the Portland Club, where he played duplicate bridge against Lord Lucan a few days before his disappearance in 1974.

“He looked terrible,” recalled McAlpine. “I’d never seen a handsome man look so dissipated. He had been drinking for days on end and was at the end of his tether.”

Bobby McAlpine was High Sheriff of Cheshire in 1994/5. His autobiography, One Shot at Life, was published in 2012, followed by My Racing Certainties in 2015. He also contributed occasional obituaries to The Daily Telegraph.

He married first, in 1956, Jane Anton, with whom he had two sons, Euan and Christopher, and a daughter, Sara. That marriage was dissolved and he married secondly, in 1981, Angela Bell (née Langford Brooke), with whom he had a daughter, Emma.

Bobby McAlpine, born May 6 1932, died June 25 2021