She has led Singapore's athletic contingent in three successful outings abroad. She was chef-de-mission of Team Singapore at the 2002 Commonwealth Games in Manchester and, two years later, Annabel Pennefather proudly headed the contingent at the Athens Olympics.
Her biggest moment as chef-de-mission came at the 2006 Asian Games in Doha, when Singapore won a record eight gold, seven silver and 12 bronze medals.
It looks as if Pennefather will assume leadership responsibilities once again this year, as sources have told MediaCorp the Singapore Hockey Federation president will be the chef-de-mission for the Republic at the 19th Commonwealth Games, which will be held in New Delhi from Oct 3 to Oct 14.
Shooter Lee Wung Yew, who has been in every contingent led by Pennefather, believes the former national hockey player is the right person for the job.
"Annabel was an athlete, and she's a well-rounded person ... she will be able to deal with the athletes, coaches and team managers and her experience will prove invaluable," said Lee, 43.
"One of the biggest challenges will be security and having the athletes adhere to unpopular security measures, as I'm very sure security curbs will be implemented."
Some would say Pennefather, a senior consultant with global law firm KhattarWong, is a lucky charm.
She watched Li Li make history when the shuttler became the first player from the Republic to win gold in badminton at the Commonwealth Games in 2002, in the women's singles.
Table tennis star Li Jiawei thrilled the nation when she reached the last four of the women's singles at the 2004 Olympics, and Singapore enjoyed her best-ever showing at an Asian Games in Doha in 2006.
Shooting, badminton and table tennis combined to haul in five gold, six silver and seven bronze medals from the 2006 Commonwealth Games in Melbourne, and Pennefather and the team she will lead in the Indian capital will try to at least repeat the feat, against some 72 countries which are expected to compete in 17 sports.
Sailor Koh Seng Leong also feels Pennefather would make an ideal chef-de-mission.
He said: "She was very approachable during the 2006 Asian Games and I remember her being very friendly and helpful. It was raining during the opening ceremony and she managed to get us to a shelter and waited with us for the bus after the ceremony ended."
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