With just one Grand Tour on the second-year Pro Continental team's schedule, all 24 riders on the 2018 roster were initially vying for selection to the team's first Grand Tour - one that begins with an historic start in the team's home country.
"We have the roster now to do maybe two Grand Tours in one year, but we're only doing one, so that makes it a bit harder for selections," Dempster told Cyclingnews earlier this month at a pre-Giro training camp in Sierra Nevada, Spain.
Dempster signed with the team in 2017 after four years with NetApp and then Bora-Argon18. The 30-year-old Australian immediately assumed an elder-statesman role along with Dutch WorldTour veteran Dennis van Winden, and the role continued into this year as Israel Cycling Academy added more well-established riders like Ben Hermans from BMC Racing and Ruben Plaza from the Australian Orica WorldTour teams.
Both Hermans and Plaza were obvious picks for the Giro roster, and the inclusion of Krists Neilands on the first roster announcement left just five more spots available. The team announced on Wednesday that Dempster made the final cut along with Canadian Guillaume Boivin, Italian Kristian Sbaragli and two young Israelis: Guy Niv and Guy Sagiv.
It was a tense few months for all the riders since team got official word of the wildcard selection, but Dempster put in the work to ensure himself a spot. In 29 race days so far this year, Dempster grabbed top 10 finishes in stages at the Tour Down Under and the Herald Sun Tour, as well as in one-day races Ronde van Drenthe and Nokere Koerse.
Most recently he was 11th at Tro Bro Leon in France and then he put on his worker hat for Vuelta a Castilla y Leon, where teammate Mihkel Raim won stage 2 and Plaza won the final stage and the overall.
"I feel like, now I'm 30 and I've been around the block a few times, I'm well equipped to handle the stress of selection situations," said Dempster, who's previously started a Vuelta in 2013 and the Tour de France in 2014 and 2015. "At the end of the day you just have to get back to focusing on the process, getting yourself in good shape, being skinny, being strong and all that type of thing.
"It's one thing to get there," Dempster continued, "but I'm not just interested in riding around Italy for three weeks and suffering at that back. It's an objective to get there and be competitive, not to get there and be selected, and whoop-de-do I'm at the Giro. It's an objective for me."
Carrying a triple threat in his toolbag
The Israel Cycling Academy have made no secret of their desire to take home a stage win from their maiden Grand Tour voyage with an historic non-European start. Winning in Israel would be ideal, but any stage win over the three weeks would be a huge success and milestone for what is basically still a start-up team. Dempster said he brings three strong attributes to the table to help make that happen.
"In the past I've always played like sort of a helper role, so in lead outs I'm quite useful," he told Cyclingnews. "But this year I've gotten top 10s in a couple of WorldTour races, so if there's an opportunity I can take it, and I will take it. Maybe on not the super-hard breakaway days there's a chance for me, some smaller group stuff or if there is a small climb close to the finish or something like that.
"On top of that, I think I fit in really well - I'm a bigger guy, like 75 kilos - so looking after Ben or Krists or Ruben, if they're going to go for those really harder finals and they need someone to put them where they need to be so they're not spending the first five minutes of the climb getting back to where they need to be, I think I fit those three roles really well."
In Sbaragli, the team doesn't have a pure sprinter to compete in the full-on bunch kicks, but the Italian is a crafty rider like Dempster who can win from a reduced bunch or on the tougher days. The team's best chance may come from a breakaway, and they've been aggressively courting the escape's all season. There's no need to stop now.
"Breakaways are really important," Dempster said. "They're valuable in Grand Tours, to be honest. You're on TV the whole day, and on top of that you never know what's going to come off. Like last year, [Sylvan] Dillier won that stage from the break, and you just never know, so I think for us, sure we need to be up there and be visible and respect the invitation.
"We've been in the breakaways all year, and it's important we continue that style of racing because we haven't got a Contador or a Froome or guys like that, but we have guys who can definitely be up there to win a stage. That's a big goal, and I think from the breakaway that could happen."
Demspter's Giro start will fill the missing spot in his personal collection of Grand Tours after having already done the Vuelta and the Tour, but he says it's not just about adding another line to his palmares, it's about the soaking up the experience.
"Just finishing and rolling into Madrid the first time was an amazing feeling, and the Champs Elysees, I get goose bumps just thinking about it," he said.
"But more than that, probably the coolest moments for me are just being in the fight for a stage win or something like that; those are really cool moments for me. I'd say that's the more important thing, so it's not like ticking off the list or that type of thing. It's the pinnacle of sport, it's a super cool thing to be a part of, and it's fun. It's hard. It's a really, really big challenge. You go deeper than anything you've done before."