He thought he had a chance today, with stage six ending with a seven kilometre climb at gradients of 8.7 per cent, including a brutal final 900 metres at double-digit gradients.
It was thought to be too tough for overnight leader Alaphilippe, but he put in a superb ride to finish sixth on the stage – ahead of Bennett. And, with Ciccone and Teuns lasting from the original breakaway to contest the stage win, two minutes before Bennett arrived, it meant instead of jumping into second overall – or first, if Alaphilippe struggled – he remained in fourth overall, ruing a missed opportunity.
"We [he and Kruijswijk] had an arrangement that if we arrived together at 900 metres and he didn't need my help, then I could try get the jersey," Bennett said after the stage.
"You just had to go, there wasn't really any advantage to drafting [to help a teammate] or anything like that – just do what you can and get to the top. I gave it a go, hoping Alaphilippe would crack – it wasn't to be."
Bennett will still work in service of the Dutch rider, noting that Kruijswijk is suited to longer climbs, and generally gets better as Grand Tours progress.
"That's a real explosive finish, and we know Stevie's really good on the long stuff. He's never been with the best in the first week, but he's always better than the others in the last week."
However, there still could be a chance for Bennett. Stage seven overnight is set to be contested by the sprinters, while if Bennett rides well, he should be able to stay with the best riders on punchy but manageable terrain on stages eight and nine. The next two stages won't trouble the general classification contenders, leaving stage 12 as the potential moment where the yellow jersey could change hands.
A 209.5 kilometre route from Toulouse to Bagneres-de-Bigorre, the stage features a 13.2 kilometre climb at an average gradient of 6.9 per cent, followed by a 9.9 kilometre climb at 7.7 per cent.
If the best climbers set a high pace on those climbs, it would surely be too difficult for Ciccone, Alaphilippe and Teuns, and possibly Bennett too. But, with 32.5 kilometres of descending from the top of the final climb until the finish, if Bennett can stay close to the best riders on the ascent - a likely scenario - he could well catch them on the descent, and finish in the lead group, without the company of his three rivals.
Of course, that depends on other riders not emulating Ciccone and staying clear in a successful breakaway over the next five stages, as well as Thomas or other contenders not claiming bonus seconds, Bennett riding extremely well, and Alaphilippe not taking time back on his specialist punchy terrain later this week.
So, yeah, it's fair to say it's a long shot. And, even if Bennett did get the jersey after stage 12, it would surely only be for one stage before he'd have to relinquish it in a 27.3 kilometre individual time trial on stage 13.
But, there remains a chance that New Zealand could have its first cyclist pull on the famous yellow jersey. And that's not a sentence that could have been written many times before.