Usually when I start a post, I have a conclusion in mind, but not this time. So if it winds up sounding pointless, well... you were warned. Anyway, Danilo DiLuca (or maybe Andy Schleck, if you believe in miracles) will win his first grand tour when the Giro pulls into Milan Sunday. In the new millenium this hasn't happened all that often, so let's look back at the Vueltas, Tours and Giros won since Y2K by someone with no history in the winners' circle. Maybe this will tell us something about the road to grand tour victory...
2007 Giro: Danilo DiLuca (probably)
Assuming DiLuca holds on, he will have won the Giro on his fifth try (?), with only one previous top 20 placing -- that fourth in 2005. Still, that was a true breakout year for a rider of whom much has long been expected, and if he slid back in 2006, it was largely beyond his control. DiLuca was a force in the Ardennes, so if his translating that Classics form into a grand tour win is a surprise, he nonetheless is a former Pro Tour champ achieving the goal he'd talked about for the last two years. DiLuca turned 31 in the offseason; he's hitting his prime a bit late, but so be it.
2006 Vuelta: Alexandre Vinokourov
Vino more than some of the others on this list was a grand tour victory waiting to happen when he took the Vuelta in commanding style last summer. Prior to his team's exclusion from the 2006 Tour, Vino had finished fifth and third overall in le grand boucle... and most of the guys ahead of him were gone. He salvaged his lost season by transferring that favorite status to the Vuelta, where he made good with three stage wins and the overall title, sealed with a win in the last time trial. Vino was 33 when he got his victory in Madrid.
2006 Tour: Floyd Landis
Little needs to be said about his post-Tour experience, but prior to his win*, Landis developed his Tour credentials as a Lance lieutenant from 2002-04, snagging a few stage race podiums along the way... including second in the Dauphine Libere in 2002. Landis' mix of climbing prowess and time trialling made him a rider to watch, so nobody was shocked when he went from 23rd to 9th to first in Le Tour... the latter leap occurring in the absence of half of the previous year's top ten. Landis was 30 when he donned the final maillot jaune.
2006 Giro: Ivan Basso
Another asterisk win... but Basso was a prohibitive favorite just hitting his prime. He was racing his second Giro, with 2005 going up in smoke due to stomach problems... otherwise he might have won. That, plus two Tour podiums, made Basso the man to beat in the 2006 Giro, a status he reinforced early and often en route to an easy win. All tainted of course, but there you have it.
2005 Vuelta: Denis Menchov
Yet another asterisk win, only this time Menchov gets the victory due to apparent winner Roberto Heras' misdeeds. Prior to his win, Menchov had shown flashes, winning the Dauphine's climber's jersey in 2002 and the maillot blanc at the 2003 Tour. The next year he won the Vuelta a Pais Vasco and a stage of the Vuelta a Espana, before quitting on stage 14. So his win of the '05 Vuelta was a bit out of the blue, but Menchov's ride in the 2006 Tour (6th overall, one stage) shows he belongs in the upper echeclon of grand tour riders. Menchov is still only 29.
2004 Giro: Damiano Cunego
With all eyes on defeinding champion Gilberto Simoni, Saeco sent his young 22-year-old lieutenant up the road to draw out the competition... and they let him go. After the Falzes stage, Simoni never had the strength to reassume leadership of the team, and the win was Cunego's. Prior to the Giro, Cunego had no [editor's note, by chris] Grand Tour track record to speak of as a pro. Subsequent wins that year helped justify his win, but this was a true shocker at the time... and still sorta is.
2002 Vuelta: Aitor Gonzales
Like Cunego, he started out as a lieutenant but when leader Oscar Sevilla lost his will to live on the Angliru, Gonzales left him in search of fame. Roberto Heras won the stage and held the maillo de oro until Madrid, but Gonzales crushed Heras in the final day's time trial by three minutes, triple what he needed to take the top step. Gonzales' career has been sidetracked by doping suspicions and ultimately a two-year ban. He was 27 when he won the Vuelta.
2002 Giro: Paolo Savoldelli
The Falcon flew away from the peloton on the ride to Passo Coe and salted the race away on the final ITT, in a race known more for who was thrown out than who stuck it out. Still, Savoldelli was a legitimate contender, having finished second in 1999 (before missing the next two editions with injuries and team issues), and Savoldelli has since confirmed his worthiness with a riveting win in 2005, along with some other highlights. He was 29 when he won his first maglia rosa.
2001 Vuelta: Angel Casero
Similar to 2002, the 2001 Vuelta came down to the final ITT in Madrid, this time Angel Casero shoving wonder-boy Oscar Sevilla aside for the overall win. But there is where the similarities end... regardless of what we might think of everyone from this era, Casero did show himself a future winner with a second place at the 2000 Vuelta and fifth in the 1999 Tour. He was also a national champion in 1998. Casero was 29 when he won the Vuelta... his last grand tour win.
Conclusion? You can steal a Giro or Vuelta, especially if you're doped to the gills. But you probably won't win the Tour from out of nowhere.