Welcome to Chicago! Ever since you opted out of your contract with the Rays, rumors have run rampant that next year would be sitting on the bench in Wrigley come next spring. Even though it hasn’t been confirmed yet, seeing how Rick Renteria is now looking for employment, it looks like those rumors are actually coming to fruition.
So I figured I’d take this chance to reach out to you, one former Tampa Bay-area resident to another, to let you know a little about your new city. Things are going to be different, way, way different now that you’re coming to the Midwest. For instance, no more “Florida residents are so weird” jokes from the late night comedians. Instead you get, “Chicago politicians are so corrupt” jokes!
|You're going to need that hoodie, and a hat, and some gloves, maybe a scarf, too.|
Let us get the main issue out of the way first - the weather. Dont' forget to pack your favorite hoodie. Yeah, winters in Chicago are a bit brutal. As a matter of fact, as I type this, it is, in fact snowing outside. The good news is that except for April, possibly a few weeks in May, ok maybe a day or so in June, the weather is pretty sweet during the summer. Dining al freso at a local farm-to-table restaurant, enjoying a nice glass of wine after a day game victory against the Reds on a perfect July 72 degree night is one of the underappreciated joys of living in this town. Not something you can really do in the middle of a sweltering St. Pete summer.
Speaking of weather - how about getting a chance to manage 81 games in Wrigley Field? Kind of an upgrade from “The Pit”, huh? (I’m kind of bummed your nickname for Tropicana Field never caught on). Sure the friendly confines are a bit of a mess right now with the first phase of renovations going on, but trust me, watching baseball in one of the true historic fields in the league. You appreciate the fact that it is a true neighborhood park (even if the neighbors get a bit grumpy from time to time).
As far as the neighborhood itself, it is quite different than St. Pete. While there is no Fergs to enjoy pre-game there are plenty of other options. I’ve read that before your wife introduced you to the wine world you were a bit of a beer and whiskey guy. Well welcome to Beer and Whiskey town! On those nights that Castro boots an easy ground ball and costs you a game skip all of those bro-joints right around Wrigley and join me a couple of blocks south at a couple of true dives.
Just pop into Monsignor Murphey’s and put the first round on my buddy Dan’s tab…I’m pretty sure he wouldn’t even notice. Plus you can get a Flubby special from downstairs. With Hot Doug’s (RIP) out of business, it’s better to go with the regular Chicago style dog than a gourmet encased meat dog. Just don’t put ketchup on it. Some guy might lose an election because he made that mistake.
If you are looking for places with a bit of a better wine list we have that covered as well. Personally I’m a fan of the Purple Pig downtown. Great wine, food is pretty good. If you’re looking for steak, Del Frisco’s has you covered as well. I understand they’re saving a very special bottle of wine for that moment you’ve been brought into town for - winning a World Series (no pressure, though). If you’re looking for something more “Chicago” then Gene & Georgetti has that old-school, rat-pack vibe to it.
Kudos to you for not backing out of the Italian restaurant you’re opening in Tampa. Nothing says sound investment like a restaurant! If you need menu ideas you are in luck because every other restaurant that’s opening in this city is an Italian joint. While I haven’t had a chance to sample them all I can say that we have everything that you could need from family-owned neighborhood joint (Volare) to sports-celebrity-themed (Harry Carry’s) to super fancy (Spiaggia). And don’t forget about Eataly - the downtown temple that worships all things Italian.
We might be losing a Michelin-starred restaurant in L2O, but there is still plenty of fine dining options around. If you put your name in now, you might get a reservation for Alinea by the time the season starts. Top Chef alums Fabio Viviani and Stephanie Izzard run pretty popular restaurants while Rick Bayless has built an empire of Mexican eateries downtown.
With the restaurant and your ties to the Tampa community I’m not sure if you’re looking to permanently relocate up here (state taxes are a bitch). If you do I hear there is some property available. Johnny Toews has a sweet bachelor pad he’s looking to unload on the Gold Coast. If you want something a little more historic, a little fixer up that used to house Al Capone is looking for a buyer as well. You might even be able to talk them down from their asking point.
|Hipster Joe Maddon|
Lakeview wouldn’t be bad for you. Walking distance to work, close to the lakefront trail and excellent dining options. You like your diners and Broadway has plenty of them. Melrose Diner, Stella’s, The Bagel and Yolk are all in the neighborhood. All of them are nice places to grab a bite to eat on the way to the park.
But, hey, if you’re in town for a few years, feel free to move around and try a couple of different neighborhoods. The transit system is pretty great (when people aren’t getting attacked by machetes) and despite the occasional delay gets you from one part of the city to another in a quick fashion. I even have an extra Ventra card laying about that you can have (saves you the $5.00 sign up fee!)
As for your actual job, let me warn you, expectations are going to be a bit higher for you. While Chicago sports fans aren’t as insane as New York fans they are a bit more loyal than your typical Florida sports fan. For one thing, they pretty much all grew up here. Luckily there are approximately 164 professional sports teams in this city (165 if you include the MLS) so some of the loyalties are a bit divided.
If you can keep the Cubs competitive from May to September you should be fine. After that attention starts to drift to the Bears, Bulls and Blackhawks. The press is a bit more jaded than what you’re used to dealing with down south, but what would you expect if you had to cover a team that hasn’t won since Roosevelt was in office? And if you do struggle, at least the White Sox fans will like you more than whoever is coaching their team.
Your are coming into a pretty good situation. There is some considerable young talent on the team. Although it might be a bit odd for you to have young offensive talent as opposed to young pitching talent. Pitching is a bit thin in the prospect department, but guest what - you have an ownership group that can actually spend money on high end free agents. No more dumpster diving for players like James Loney and Roberto Hernandez!
|See, they weren't always at odds with each other!|
Remember how much fun you had with BJ Upton and his occasional “lack of hustle” and “mental breakdowns”? Luckily for you Starlin Castro is still a Cub. You’ll get to bench him at least once or twice this season for not running out a ground ball or forgetting how many outs there are in an inning. That way you can earn some street cred with the press while still being a friend to the players.
Of course, there is the outside chance that Castro is moved to some other team this off-season to help out with the pitching situation. If that happens, Javy Baez can step in. Don’t be worried about his strike-outs. The kid hits wherever he goes. He’ll figure it out. Jorge Soler has the best bat speed I’ve seen since a kid named Sheffield. Not a bid duo to build a playoff team around - and we haven’t even mentioned Kris Bryant or Anthony Rizzo yet.
You’ve already done what a lot of people didn’t think was possible - take a team that was a laughing stock because they had never won anything in the Tampa Bay Rays and make them respectable. Now you get to take a team that is a laughingstock because they are the Cubs and hopefully make them respectable as well. Good luck with that.
See you at the Convention in January.
P.S. It’s tradition that when you move to Chicago you crash on someone’s couch for 3-6 months. If you need a couch to crash on, just hit me up.
P.P.S - If you could hook me up with tickets for the Foo Fighters when they play Wrigley this summer, that would be great!