The record has been eclipsed a few times since 2008, and sits at 33 hours and eight minutes. With the passing of each anniversary of his friend's death, James has felt a pull towards doing the marathon again.
He says the desire to do it has never been in short supply.
"The motivation is just to help the foundation. We've been working closely with them. Knowing what the children go through with cancer and knowing what their families go through - it's incredible how strong they all are. So there's huge motivation to be raising money for that."
Both James and Brett have been lifelong devotees of squash. Brett, 51, plays in masters' series tournaments, while 24-year-old James has represented New Zealand at junior level and still plays competitively. While their base-level fitness might be good, preparing for such an arduous event requires scrupulous attention to detail.
"We've been doing six-hour sessions and training once or twice a day for the last six months," says James. "Even though we've done it before, it's very hard to say what's going to be sore on the day. The last time we had everything bandaged up and I had every individual toe plastered."
The risk of bad blistering is so great that James has been soaking his feet in methylated spirits to harden them up.
"We've been careful about selecting certain types of socks because [they] are a massive part of it. Normal cotton socks can make you blister
because they hold a lot of sweat in them. We found a company that create merino socks that evaporate water."
They also have a nutritionist on board who will be helping them with their food and water intake throughout the gruelling 36 hours of playing.
If just making it through the time wasn't hard enough, James and Brett also have to be careful in the way they record their efforts to make sure they come up to the fastidious evidential obligations required to break a Guinness record.
"We've got a 30-page [book] that we need to go through with a fine-tooth comb," says James.
"We need witnesses there, we need stewards, timekeepers ... there are a lot of things we need to do!"
One of the conditions is that they are only allowed a five-minute break after every hour of play.
James says they will try to accumulate break times so they can have bigger rests when they most need them, which is likely to be in the middle of the night.
"From about 1am to about 6am [is] the most challenging. Your body knows it needs to be sleeping and you've got to fight through it.
"And honestly, it can get a little boring on court. It becomes quite monotonous. It's a huge mental struggle."
To help pull them through, the Howick Squash Club has organised social events to run throughout the 36 hours.
Sponsors have provided James and Brett with $3000 worth of gifts that will be sold in raffles and silent auctions, with the proceeds going to the Child Cancer Foundation. The foundation's business development manager, Liz Atkinson, says the organisation is incredibly humbled by James and Brett's commitment.
"We receive no direct government funding," says Atkinson, "so we rely on the generosity of New Zealanders to support or work."
Record bid
What:
Guinness World Record attempt for the longest squash marathon
When:
Saturday, April 11 to Sunday, April 12
Where:
Howick Squash Club
To support James and Brett in their goal of raising $36,000, visit:
https://give.everydayhero.com/nz/squashworldrecor
