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First, it's worth checking out if you haven’t seen the report yet. It’s a fascinating discussion that re-emphasizes the human element of the tidal wave of transactions throughout the year.
I’ll go out on a limb and predict that most around here have effusive praise for Chicago; hell, I live in New York nowadays, and I still tell everyone who asks that it doesn’t even belong in the same conversation as the Windy City. Chicago has so much to offer to anyone and everyone that it’s hard to believe players would consciously hold it against the Cubs for playing there.
I won’t pull up crime statistics or engage with political talking points here. They are important topics that deserve our undivided attention, and they’d obscure the smaller discussion we’re having now.
Data points are pointing both ways on this. Shohei Ohtani reportedly didn’t even visit the Cubs during his free agency saga, maybe because he knew he wanted to remain in Los Angeles with the Dodgers from the onset.
Dansby Swanson repeatedly said how much he wanted to come to Chicago after signing with the Cubs, though perhaps he was merely incentivized to do so because his wife, Mallory, is a star forward for the Chicago Red Stars of the National Women’s Soccer League.
It’s hard to pinpoint any consensus on a broad topic, especially given that a player’s decision of where to play is rooted in personal preference. Players - both as Cubs and as Cubs’ opponents - have routinely lauded the Cubs faithful as among the best fans in baseball.
Though it’s practically impossible not to engage in confirmation bias with such a statement, it feels grounded in some reality. The Cubs routinely rank near the top of attendance rankings year in and year out, regardless of whether they’re World Series contenders or amid another rebuild.
The surrounding area of Wrigley Field, particularly Wrigleyville, is often cited by players as one of their favorite places in the city. It’s relatively serene, and the Chicagoans are usually respectful toward players and their privacy. Remember when Ben Zobrist rode his bike, in full uniform, to a game at Wrigley?
Not to bury the lede, but winning matters, too, especially for older free agents. Though the Cubs have had some really, really (really) high-highs over the last decade, they’ve sandwiched that window of contention with two separate rebuilds. For a team in such a big market, that kind of rapid vacillation between the elite contenders and bottom-feeders of the league could be a huge turn-off to guys who are singularly motivated by winning.
Again, there is so much more to say in this conversation. Illinois income tax rates, North Side vs. South Side benefits (and drawbacks), the political leanings of Chicago, the harsh winters, and a near-infinite myriad of other subjects factor into the at-large discussion. For the sake of this article - and keeping it within the context of the report on the Giants - it’s fair to say that Chicago, for all of its unique features, also will rub certain players the wrong way.
Of course, the same can be said about any city. And, not for nothing, money often talks most during the pursuit of players. A player may not be in love with coming to Chicago, but if the Cubs’ are the highest bidder for their services, their attitude might change quickly.
Now, if only the Cubs would flex their financial might and spend some darn money.







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