In Honor of Baseball Season…I present, My favorite parking spot


Some people have asked for me to “share more about me” in my blog.  Not sure why anyone would want to know more about me, especially when I can write about Style and the Chicago Bears which I find much more interesting. I am not interesting.   But I do have some fun stories that I’m happy to share.  And, I do enjoy reliving fun memories, so I have decided to share some “Terry stories”, so I can laugh and giggle when penning my blog.  I will feather in some of these stories throughout the year.  To write them all in a week or month would be an embarrassment of riches.  And I am not rich. 🙂

My Favorite Parking Spot

I get invited to a lot of Cubs games.  A lot.  Upwards of 20+ games a year.  Typically corporate events and the majority at one of Wrigley’s Rooftops.  Which is a party on a roof, which happens to be within earshot and possibly eye shot of Wrigley Field. It’s not that I don’t like baseball, but if I’m going to spend 4+ hours at a sporting event, it should probably include a football, basketball, tennis ball or hockey puck.  Baseball would be #5 on my list of sports. The good news about the Rooftops is they have more restrooms per capita, than Wrigley Field has this week. #ZING


That being said, I do enjoy a fun party and attending these events is fun as well as a big party, so I have been known to partake in my fair share of games.  Wrigley Field is also a great place to take in a baseball game, even if you are on a rooftop and not inside the actual ball-field.   Second only to my all-time favorite ballpark, AT&T Park, where the San Francisco Giants play (and win World Series…a tad different from my Cubs).  Have I mentioned that at AT&T Park they serve Stella and wines from Napa?  The Cubs serve Old Style.  Or Budweiser.  #Choices  #Decisions


Me and the kids at a game in San Fran last summer. 🙂  But I digress…

So, going to Wrigley Field to watch the Cubs play, can be super fun, but parking is a nightmare.  There is basically NO public parking around Wrigley Field.  You either have to park a mile away to find street parking and walk, which isn’t the worse thing in the world, but that also means to you to walk a mile back to your car and I prefer making things easier for me.  Sometimes it’s dark when you leave the game so it’s not always safe to walk a mile in a big city in the dark.  There isn’t a parking garage or a parking lot so if you are driving to a Cub’s game, you need to be “creative”.  Hence, how I found my favorite parking spot.


Surrounding Wrigley Field there are restaurants, bars and apartment buildings and condos.  Behind some of these buildings are alleys.  Google it if you don’t know what I’m talking about, because I cannot get off on another tangent about alleys.  Yes, I will land this plane.  So… behind these apartment buildings in these alleys, are “residential parking”.  These residents have made it a business…a very lucrative business, to rent parking spots from anywhere from $20 to $40/game.  Probably up to $100/game if the Cubs were to be in the World Series, but we don’t need to worry about that (or didn’t until this year, because “This is our year”)>  The best part about these spots, is they are right behind Wrigley Field.  So, you can basically “rent” a spot from someone’s “home”.  This is a great option for me as it’s close and convenient.  The only issue is sometimes they stack the cars to get the most bang for their buck,  so unless you indicate you want “easy in and out”, and pay accordingly, you may be stuck until the person behind you gets their car.

Hello Lenny!

So a few years back (actually probably more than 3, because I was driving a Porsche Cayenne at the time, and I am on my 2nd car since that) I was driving to a Friday afternoon game, and was driving behind Wrigley Field looking for a parking spot (I wasn’t aware at the time that residents rented their spots out) and a man holding a sign that read PARKING $25 waved me over.  I unrolled my window and he asked if I was looking for parking.  Yes sir, I am.  He indicated he has a spot for $25.

Terry:  Is the spot easy out?

Lenny:  Yeah

Terry:  I know you say it’s easy out, but, I really need easy out.  I can’t be waiting 30 minutes for you to jockey cards around.  I’m a doctor and I’m on call, so it’s imperative I have easy out.

Lenny:  Yes, it’s easy out.  Follow me, Doctor.

Those who read my blog, know I am Not a doctor, but that’s neither here, nor there.  I like the option of leaving early, if needed, so a girl’s gotta do what a girl’s gotta do.  So I drove and followed Lenny to an absolutely fabulous spot. Literally 1/2 block from Wrigley Field.  I paid him $25 and off I went to the game.

True to being who I am and getting bored and missing my family and wanting to go home, I left around the 7th inning and walked back to my car.  There was Lenny, sitting in a chair, next to my car, keeping an eye on it.  I kid you not. He sat next to my car, for what I can gather was the entire game and watched my car.  How endearing, or creepy, but I like to think endearing.  I thanked him (didn’t tip him just said thank you) and he handed me a card with his name written down with a phone number (which is how I knew his name as you don’t always know the name of the parking attendant) and said that anytime I wanted to park, give him a call and he’d make sure I had a parking spot. An “easy out” parking spot!


The next time I went to a game, I was driving in the same area looking for Lenny (I didn’t call him first), and happened to see him Waving me down from the end of the block.  Literally jumping up and waving at me.  I believe he was happy to see me.  I mean, who wouldn’t be. 🙂

Lenny:  Dr. O’Brien, I have a great spot for you.  Closer than last time.

Dr. O’Brien:  Great!

Lenny:  It’s further down the alley but closer to Wrigley, can I hop in your car and  drive  down with you?

Dr. O’Brien:  No problem. Hop in.

Lenny hopped in, and my spot was so close, I could throw a baseball and hit Wrigley…and I do not have a great throwing arm, but can throw a perfect football spiral.  Don’t ask me how, I just can.  It was just about the best parking spot for a game at Wrigley Field ever.  Yes, Best. Parking. Spot. Ever.

The 3rd time I drove down, I had a friend with me, so I called Lenny in advance and told him I was coming down, with another colleague.  When we approached our parking area,  I saw Lenny, and he was waving at me.  He was expecting me.  Nancy was in the front seat and I drove up to Lenny, and rolled down my window.

Lenny:  Hi Dr. O’Brien.  I have another great spot for you.

Dr. O:  Hop in.

Lenny jumped in the back seat and off we drove to our parking spot.

Nancy and Lenny exchanged general pleasantries.  She gave me a look indicating she thought I lost my marbles, but she was delightful and pleasant to my parking valet, Lenny.  I figured I would explain all during the game.  And here’s where it really gets good.

Lenny:  Dr. O’Brien, I made you a CD.

Did I mention Lenny is a Rustafarian?  He looks like Bob Marley.  Based on his CD, he sounds like him too. I mean, how sweet he made me a CD of his own music.  A CD of His own Reggae Music!  And, it was really good.  We listened to it on the way home from the game and it really was great.


My friends say only I can befriend a Rustafarian parking attendant (I use that term loosely, “parking attendant”, not “Rustafarian”, as he was a Rustafarian) and end up with a Reggae CD.  Yup, that’s me.


I parked with Lenny probably 6 more times that year and each and every time I’d come back from the game , he was watching my car.  He was like my own valet and bodyguard.  All for the price of $25.  Or $30.  Or $40, depending on my mood.   I always knew nothing would happen to my car and knew nothing would happen to me.  Lenny had my back.  (Now glancing up at this paragraph, when I say, “I parked with Lenny”, I mean I parked my Car with Lenny.  Just want that to be clear… ).  I also parked my car with Lenny the following year.  Easy. Peasy.  He never asked me what kind of doctor I was.   I believe it was professional courtesy.  But if he did ask, I’d say Pediatrician.


All good stories must come to an end, as the 3rd year when I went to the Cubs game I couldn’t find Lenny.  I asked around and was told that the owner said Lenny didn’t give him all the money owed him, so he was “fired”.  My personal valet and body guard was fired.  Life is so unfair.  And it would have made a much better story if I were to find out he was a popular recording artist, but that only happens in movies.  I don’t know what happened to Lenny.

It was fun while it lasted. 🙂

Song of the Day:  One Love by Bob Marley

One love, one heart
Let’s get together and feel all right
Hear the children crying (One love)
Hear the children crying (One heart)
Sayin’, “Give thanks and praise to the Lord and I will feel all right.”
Sayin’, “Let’s get together and feel all right.”

Maxie picture of the day.  Sweetest puppy ever.  Same pose.  Different day. She really does a great job, sitting.


Mer and I finished binge-watching Bloodline.  Fabulous.  If you can, binge-watch it this weekend. I’m considering re-watching all 15 episodes.   Kyle Chandler truly delivers.  I’m predicting another Emmy Award for him.  My new favorite actor!  Now I need to revisit Friday Night Lights to see more of Coach Taylor.  Football and Kyle Chandler. Best. Weekend. Ever.

Peace out and Play Ball!



excuse me BRB










  1. Great story T!
    I also just watched Bloodlines-lost a lot of sleep until I finished. Remember Kyle Chandler in the show where a cat would bring the next days newspaper and he went out to try to stop bad things from happening?

  2. Truly, Mer and I started re-watching it. I don’t think I ever realized what a fantastic actor, Kyle Chandler is. I only watched bits and pieces of FNL, so that’s on my bucket list! 🙂

  3. Yes, and while I exchanged general pleasantries with Lernny, I also had dialed 911 on my cell phone and was ready to press ‘send’ at a moment’s notice! Yes, I certainly thought you had lost your marbles! And while I know Lenny ‘had your back’ with your parking space, I was afraid of a possible ‘knife in the back’ while driving around the block with a total stranger …. at night! And a stranger who knew you as Dr. O’Brien!

    Of course, the story got funnier after each beer at the game…. and in the years since that escapade!

    Love Lenny!

    Thanks for the giggles this morning, T!

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