Guess Who - Game

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Male? Yes
Active? No
Has a name that contains a 'q'? No
Did he retire before the year 2000? No
Born south of Vienna? Yes
Mainly GC-rider? Yes
Born north of Madrid? Yes
Born east of Reykjavik? Yes
Born west of Moscow? Yes
Did he ever win a stage race in the current World Tour? Yes
Did he formally retire or was there another reason he ceased to be active? Yes, he did
Did he cease to be active before 1/1/2010? No
Did he cease to be active before 1/1/2015? Yes

Born east of Madrid? No
Could he, from his birth-place, ride to Madrid within a day? (Once the lockdown is completely lifted.) Yes
Must be from Galicia, Asturias , part of Cantabria or Castilla y León, or the Comunidad de Madrid.

Did they win a Grand Tour? I'm leaning towards Juanjo Cobo, but there's still a few it can be.

Edit: would be quite a ride for Torrelavega to Madrid in one day.

Sastre, then.

Jesus wept, Libertine, the Tour de France isn't in Spain and Leganes is southeast, not east, of Madrid. Cuesta and Gómez Marchante are from the right provinces, but both born east of Madrid. Gustavo César is still active. Aitor González and Ángel Casero are retired too long, which means that unless we're counting Heras' Xterra and Brompton racing as activity El Bisonte should be the one guy remaining.
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Volta a Catalunya Spanish winners in a reasonable timeframe:
Fernando Escartín X (retired pre-2010)
Triki Beltrán X (retirement not of own volition)
José María Jiménez X (retirement pre-2010)
Joseba Beloki X (born east of Madrid)
Roberto Heras ? (does his post-suspension disappearance count as retirement, and if so is it of own volition?)
José António Pecharromán X (retired pre-2010)
Miguel Ángel Martín Perdiguero X (retired pre-2010)
David Cañada X (born east of Madrid)
Gustavo César X (still active)
Alejandro Valverde X (still active)
Joaquím Rodríguez X (retired post-2015)

Vuelta al País Vasco Spanish winners in a reasonable timeframe:
Íñigo Cuesta X (born east of Madrid)
Aitor Osa X (born east of Madrid)
Iban Mayo X (born east of Madrid)
José Ángel Gómez Marchante X (born east of Madrid)
Juan José Cobo X (you've confirmed not him)
Samuel Sánchez (retired post-2015, not retired of own volition)
Alberto Contador X (born south of Madrid. I guess his suspension could count as "ceasing to be active" between 2010 and 2015?)
Ion Izagirre X (still active)

Vuelta a España Spanish winners in a reasonable timeframe:
Ángel Casero X (retired pre-2010)
Aitor González X (retired pre-2010)
Contador, Valverde, Heras, (Cobo).

Unless we're counting Álvaro Pino's time until 2010 managing Xacobeo as activity within the sport?

(Although it would be hilarious if we were making such a complete hash of finding Alberto freaking Contador, mind)
It was Itzulia not Catalunya

José Ángel Gómez Marchante

San Sebastián de los Reyes is NE of Madrid so no good (unless classed as part of Madrid)
Yes, it is him. I don't think his hometown can be classified as east of Madrid to be honest. Cettainly not west of it either.

I also thought about Contador still being a possibility but he fell to the retirement criterion.