I dont think being jaded has anything to do with it. Sure, there are many players who grew up a fan of a certain team, Cubs or otherwise, and would love nothing more to actually play on that team. Probably doesnt happen that often.
Players are happy to just be part of any team, whichever team has shown interest in them, drafted them, traded for them, whatever. It is sooooooooo difficult to make it to the show, you cant be choosy in this regard. You go where/when someone will have you. The tens of thousands of players all over the USA, Latin America, Far East and other locales are all trying to gobble up just a precious few spots that are available. Only the very best players make it to the show, after having passed by many other talented players.
All that said, sure, I'm sure many players would welcome the chance to be part of MLB history on a Cubs WS team. I suspect there would even be possible FA's out there that might opt for a role here even when other options are available to them, for that challenge and opportunity of a lifetime.
But, to answer your query, I dont think players care all that much where they win, just as long as they do win, somewhere.
90% of today's players would play in H-ll if the money was right. IMO
When Hendry was here alot of players wanted to be part of Cubdom. (probably those ridiculous contracts he liked to hand out)
I think the same will be said about Theo/jed.
Actually i'm thinking that players know what there gonna get with Theo he's been around the game long enough to have dealt with almost every FA since 2003.
I'm sure he has a good repoire with most agents and if a player really wants to play here and Theo wants him, I think the odds are pretty good said player will be in a Cub uniform.
It's just a hunch.(or wishful thinking) on my part, but I really believe that will be the case.
"90% of today's players would play for the Snotz at the Cell, if the money was right. IMO"
There, I fixed it for you. As you stated, the players go where the money is.