He was hoping to go out captaining the team of the second-only Australian to win the Tour de France. Those plans turned to dust on the road to Roubaix, when Richie Porte crashed less than 10 kilometres into the ninth stage.
Professional cycling is like that. Professional sport is like that. Life is like that. You don't always get what you want.
"I know I'm not the biggest engine in the peloton but I have some all-round abilities and I try and make the most of that."
The dimple-faced 38-year-old from Mansfield did get to chose when he would go, however. Not so much a rarity, though after 15 years at the highest level of his chosen métier, a privilege nonetheless for one of our country's most accomplished cyclists and winner of the Sir Hubert Opperman medal in 2014.
In much the same way he entered, it was with little fanfare that Simon Gerrans announced his retirement as a pro cyclist.
Despite winning the Under-23 title in 2002 - the first year the road nationals were held on the infamously difficult Buninyong circuit - courtesy of his fifth place in the elite men's field, he struggled to nab a pro contract. The very attributes that made him such a force a decade later - that he was neither a sprinter or climber or rouleur, but a combination of the aforementioned - initially made him unremarkable in the eyes of a top-ranked team, at least to the point of being offered a job.
After cleaning up on the French amateur circuit and a second stagiaire opportunity in 2004, AG2R Prévoyance finally gave him a chance to join the big time. Overall victory at the 2005 Herald Sun Tour didn't set the world alight but his win at the following year's Tour Down Under - the first of four crowns in Australia's premier stage race; a feat unlikely to be repeated - did. Against far more credentialed rivals, it was not just the way he took on the race - he held the lead from start to finish - but who he beat including defending champion Luis Leon Sanchez of Spain, now a four-time Tour de France stage winner, who, despite his best efforts, could only finish second.
While it wasn't a win in Europe it became the fillip for further success, because from that point on his palmarès grew with haste, and so did his reputation as one of the wiliest in the bunch. In the space of two seasons, between 2008-09, he would win stages in all three Grand Tours and land his first major one-day race victory, at the GP Ouest–France (now the Bretagne Classic) in Brittany. In 2010, the first of two years with Team Sky, after he finished in the first 10 at all three Ardennes Classics, most pundits believed it would be sooner rather than later before one was his - yet it wasn't till a month shy of his 34th birthday that he cracked La Doyenne, Liège–Bastogne–Liège. (The others, Amstel Gold and La Flèche Wallonne, though he came close in the former, eluded him.)
"The times I was able to outsmart an opponent in a high pressure situation and beat someone stronger was satisfying."
Groundbreaking because no Australian had won previously and none since, it will not be considered his best or most memorable. It could be argued, however, that most of Gerrans' scalps weren't typically memorable for here was his modus operandi: ride as economically as possible till the final; chose the right moves, follow those moves; then with the finish line in sight, utilise his finishing speed to land the killer blow. He wasn't nicknamed 'The Sniper' for nothing...
Even the one most regard as his finest, the 2012 edition of 'La Primavera', Milan-San Remo, was the source of much consternation among fans and pundits alike. A thrilling finale saw him latch onto breakaway instigator Vincenzo Nibali as they neared the summit of the famed Poggio, with Fabian Cancellara powering across to the pair; Gerrans did only the bare minimum in the run-in to the finish on the Italian Riviera before launching his trademark killer kick to out-sprint his two more popular rivals.
Swiss superstar Cancellara, who ran second, said: "The others were on my wheel. Gerrans gave me two turns." That was enough for the cycling Internet forums to go into overdrive. Fans of Spartacus decried he'd been robbed even though he never said as much. Unfairly, the trolls claimed the Australian had simply wheel-sucked his way to victory - at the same time ignoring the fact that Nibali had ridden no different, whose reason for not cooperating was that his team-mate Peter Sagan was in the group behind. Gerrans, too, could've done nothing, for he had defending champion Matthew Goss in the same group as Sagan.
In the post-race press conference, an uninformed journalist wondered aloud if the then Australian champion had "stolen" victory from Cancellara.
"I'm pretty good at analysing the situation and making the most of what I have. I know I'm not the biggest engine in the peloton but I have some all-round abilities and every now and then I get to race for the win, and I try and make the most of that situation." Understanding your strengths and weaknesses, and responding as such while taking advantage of your opportunities... Hardly a criminal offence, certainly not in professional sport.
Upon announcing his retirement this week it's clear he feels no different, nor has he any regrets about the way he raced or how his success was earned.
"What made the biggest victories of my career the most rewarding was knowing that I perfected the preparation. During the best years of my racing career, those times when I got my preparation just right, I was competitive in the biggest races, against the best cyclists in the world," Gerrans, in an open letter published on his Facebook page, wrote. "I thoroughly enjoyed the tactics of cycling; the times I was able to outsmart an opponent in a high pressure situation and beat someone stronger was satisfying."
Isn't that part of the beauty of cycling? That the strongest doesn't always win?
He also said "my fondest memories don't come from winning classics or Grand Tour stages, but the happiness and joy my victories created for the team and the people close to me. I also cherish the times when I was able to contribute to the personal success of my teammates." While no one can deny the discipline he showed towards his sport and preparing for objectives or handling the pressure of leadership, there were a few occasions where he appeared to struggle with the idea of riding for someone else, at least one person in particular.
In 2015, Michael Matthews was an emerging talent not dissimilar to him, only 10 years younger and on the same team. At 24 years young the former was enjoying another breakout season; Gerrans could not seem to take a trick, crashing five times in the first half of the season and again at Le Tour, where he was forced to abandon with a broken wrist. Matthews was involved in the same crash but soldiered on to Paris like the walking wounded. An extended period of recovery followed by a series of tune-up races in September, he looked in excellent shape leading to the road world's in Richmond, Virginia. Gerrans recovered to ride the Vuelta but appeared to be missing a little something.
Both went in as co-leaders in Richmond though according to Matthews, if it came down to a sprint finish, he was the man.
In the final lap Sagan was away but not by much. Gerrans did not help to close down the Slovakian nor did he lead Matthews out, who nevertheless won the reduced field sprint for second. It was the height of a generational feud that continued the year following at the Amstel Gold Race and then at the Tour, and was only solved when Matthews left for Team Sunweb in 2017. So pivotal was Gerrans in GreenEDGE's fortunes between 2012-14, team management in Matthew White and Shayne Bannan were unable to ask their favourite son to pass the baton.
In October 2008, upon his retirement as a rider and before taking a role as a DS, Bradley McGee, another highly decorated cyclist and the first Australian to wear the leader's jersey in all three Grand Tours, told me that he felt the best directeurs sportifs were those who had tried but failed to accomplish a number of goals in their own career. In the sense that you don't normally see Grand Tour champions or highly successful team leaders transition to such a role or have the desire to, the statement appears to hold true.
It may in part explain why Gerrans, whose palmarès must surely rank in the five most successful road cyclists Australia has produced, has made no mention of moving to a seat in the team car, expressing his initial desire to "gain some experience and develop my skills in a new area".
"I hope that the skills and attributes I have developed and the networks I have built throughout my cycling career will provide a solid foundation to support this goal. The idea of getting out of my comfort zone and embracing a completely new career is daunting, yet excites me, and for these reasons I know it is the right thing to do."
It's easy to fall back into same-old, same-old. Far harder to begin anew, even in the face of failure. Whatever Simon Gerrans chooses next, I don't doubt he can do it.