Why Weiss entered ocean classic at 2am – and after a few rums

American sailor Andrew Weiss entered the Sydney to Hobart on his iPad at 2am one morning after knocking back a few rums on a New York Yacht Club cruise.

For months he’d been weighing up whether to haul his 43-footer Christopher Dragon across the Pacific ocean and enter a race he had watched on television since he was a kid, and he finally made the decision as the bright lights of Manhattan twinkled in the background.

“Last February, friends of ours on Warrior Won said they were entering and I said, ‘God damn, they’re going to be going down here and we’re not doing it’, so I spent months and months and months talking about it,” Weiss said.

“We were on our powerboat and drinking Mount Gay at 10 o’clock at night and my wife and one of the crew members said, ‘You know when you’re 70 years old, you’re going to be kicking yourself you didn’t do it’. Everyone went to sleep and at two in the morning I pulled up my iPad and pressed the enter button – now I’m committed.”

At last the keel was in motion.

But there was still much to be done and intelligence to be gathered for Weiss’s crew which has zero experience in the Sydney To Hobart.

Despite his rookie status, Weiss knows what awaits Christopher Dragon in ‘s Ocean Classic having watched the race religiously for as long as he can remember.

It’s long been a Christmas tradition in the Weiss family to observe the start of the race, which falls at about 9pm in their time zone on December 25.

He’s well aware of the tragedy of 1998 when six sailors lost their lives and the chaos that abounds at the race start every year. Weiss was glued to the screen from halfway around the world 12 months ago when super maxi CQS almost capsized while still in Sydney Harbour.

So he’s spent the past six weeks chasing information, trying to learn everything he can for his once-in-a-lifetime trip to Hobart.

“I talk to anybody I can talk to,” Weiss said.

“We came to the cocktail party the other night with my son, my wife and I, and I said we’ve all got to split up and talk to different people.”

Each member of the Christopher Dragon team has also been tasked with watching two previous Sydney To Hobarts, and reporting what they’ve learned to the rest of the crew.

Weiss is determined to leave no stone unturned in his quest to complete the race.

“We’re running an expedition each day, we’ve been pretending to do this for a month-and-a-half,” Weiss said.

“The other thing we’re trying to do is make sure that everything doesn’t break. The biggest things are the mainsail ripping, the rudder or mast.

“We pulled the mast out in August, analysed that. We decided to bring two mains on ours for the race because we’re only going to be here once, we’re not going to go home with a ripped main.”