Still Gotta Come Through Chicago

Report For Training Camp

Happy Friday Chicago!

Let me let you in on a little secret: for the first time, I’m a little bit worried about Caleb Williams.

He officially signed his deal this week. He’s a Bear, and players report to training camp today. It’d be a cause for celebration if I could get this nagging concern out of my head.

Part of why Williams took so long to sign his contract, apparently, was due to him and his camp looking for creative ways to be paid out. Pro Football Talk reported that Willams explored getting paid as an LLC, or getting paid via a forgivable loan. Both would come with certain tax benefits.

And, listen, that approach is far better than following the player path of yesteryear, and spending your signing bonus before you get to training camp.

But weaving in and out of tax laws comes with its own red flags.

Everyone knows a guy like this. He’s figured out the tax code, and you’re an idiot because you haven’t done this or that. He’s got business ideas, he’s got a YouTube account with too many watched minutes logged, and he talks to your Dad for too long about what he does for a living.

He may or may not be interning in personal wealth management.

It’s not the skirting taxes that is the problem, per se. I’m not sure anyone thinks all of their tax dollars are being reallocated by Uncle Sam in a perfectly just matter.

What it’s really about is what else that means about the person. You don’t stay in touch with the guy that was exploring opening up LLCs in his early 20s because it was a “no-brainer” move. His nature is most likely off-putting, in a general sense. Four years after none of his business ideas have come close to fruition, and he’s saved $376 dollars on taxes, he’s fallen on hard times. You feel bad for him until you remember the condescending tone in which he explained these “simple” finance tips and called your college major “useless” under his breath.

Sometimes when I walk down a Chicago street in the summer, I’ll see an attractive girl. But then she’ll abruptly start loudly, obnoxiously and demonstrably barking into her phone — clearly to a friend, and clearly about some inconsequential nonsense. Immediately, her persona in my mind and that fleeting moment are ruined.

That’s what it feels like to meet a guy who seems like he’s worth talking to, only for him to ask if you use a standard savings account. Time to head to the bathroom.

The tax shortcut game is just a gateway to being a guy that tells people in the bar that he could triple their salary right now, even though he doesn’t have the authority to hire people.

Williams strikes me as a guy who found out what compound interest was a week ago. And now, he’s got his own private equity firm.

The difference between him and the general tax skirter is that he actually will have the resources to act on some of these ideas. Let’s just say I wouldn’t be surprised if the Caleb Williams and SEC were in the same headline together a couple years from now, in an article unrelated to football.

I’m not a guy that sees a football player having fun and then immediately tells him to “study his playbook.” Newsflash, much to my chagrin, a lot of grown up and successful dudes like to play video games. That’s all good, as are any of their other interests.

But this one just spells trouble to me. I can only imagine Ryan Poles having to make an inquiry to the NFL saying, “Caleb wants to know if he can be paid in the form of a forgivable loan” and having to act like he was genuinely wondering what the NFL was going to reply.

“Uh, no.”

Williams is only 22, so it makes sense that he has these quirky ideas that he believes in. Young men are impressionable, and we all have some embarrassing stories from the days when we thought we had the world figured out.

I used to watch those YouTube videos where there’s random scenes from a movie playing and there’s a guy narrating a motivational speech in the background. I’m talking every morning.

So, I get it, to some extent. But would I have rather found out that him signing his contract was delayed because he punched a dude in public that called him a bitch? That question that I personally just posed is not for me to answer.

But I just hope Williams can form meaningful relationships with his teammates without involving them in pyramid schemes or convincing them that the IRS doesn’t come after individuals who open up charitable organizations on the side.

Just give me the chance, Caleb, to not have to be thinking on a random Wednesday night — alone in my apartment — “this guy just doesn’t love football enough.” I want to keep the meatball fan in me tucked and stored away.

But that’s Christmas Eve, right? I’m writing this the night before the Bears open up a season full of promise. Santa may not come, and Caleb may be slightly annoying.

Just win, baby.

In actuality, it’s hard to encapsulate how excited I am for this Bears season. I get the chills in the middle of the workday thinking about waking up on a cold Sunday knowing a meaningful football game will be played in Chicago in a matter of hours.

Players report to camp today, and in less than two weeks, the Bears will play in an actual game.

They are a part of the Hall of Game game this year, which famously teases us all into thinking football is back until you watch it for five minutes. But I’ll be watching every second of this one. That’s on August 1!

The Hall of Fame game will be especially cool this year because of all the Bears being inducted. The class includes — in order of importance — Steve McMichael, Devin Hester, and Julius Peppers.

Obviously, I’m glad McMichael finally got his due and lived to see the day where his life’s work was rewarded with the highest honor in football. But, I also wish that — if the voters really found him worthy — they could have done so before he was incapacitated. That, in some ways, even feels even more cruel to me.

Devin Hester was as no brainer as it gets. It’s a fun exercise to think about your favorite Chicago sports players in this context: “Will I be telling my kids and grandkids about this guy?”

Hester is that kind of player in two ways. For one, he is just one of the best NFL players of the 21st century. He was so much better at what he did than anyone else doing it that he is literally “beyond comparison.” Also, by the time my kids are watching football, they’ll be unable to conceive the fact that kickoffs used to actually result in touchdowns for the Bears on a regular basis.

I’m very happy that man is getting his due. Sometimes it actually feels like he is an underrated Chicago sports figure. There was a period where the Bears only ever had electric players on defense. With Hester, who defines electricity in a sports context, the defense and him were our best chances of scoring.

Julius Peppers was unbelievable, but I’ll remember him far more as an opponent — in those Bears-Panthers matchups, and later on when he was in Green Bay.

And then, five days after the Hall of Fame game, we get the debut of Hard Knocks.

And when this comes on, it won’t just be the first time we ever get to see the Bears on the show. It will also not mean that school is right around the corner, which is great. Instead, I’ll just have to continue to work for a living.

Get those last beach days in, and enjoy the farmer’s market while you can. It’s about time to #LOCKIN.

Can’t wait.

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If you take a global view of the Cubs record at the All-Star break, it’s disappointing. If you take a more pointed view, it’s just fine that they’re four under and in last place in the NL Central, considering these last couple of weeks.

I wanted four in St. Louis, but knew that wasn’t going to happen. Yet after last Friday night’s win, I thought there was a chance. Those chances were squashed in the first inning of the next day’s game.

Taking a global view of that series, too, a split is just fine — especially considering the fact that Shota Imanaga and Justin Steele did not pitch. But, man, did that latter Saturday game get away. The difference that one game would have made on our psyche heading into the second half.

The Cubs are four games below .500, 8.5 out of first in the NL Central, and 3.5 games out of a Wild Card spot.

The vibes are high, but they are delicate. This weekend series against the Diamondbacks is a must-win, in other words.

I’d like them to be .500 by the next time I write to you all.

But let’s take a step back for a second and consider those aforementioned vibes. Since the fourth of July, the Cubs are 7-3. Shota threw a scoreless inning in the All-Star game. Kyle Hendrick’s corpse delivered a 7-inning gem last Friday, improving his ERA against the Cardinals in his career to 2.51.

All of the Jed Hoyer criticisms (and defenses) stand, but his Michael Busch play seems to be working out swimmingly. In addition to Busch being the Cubs most consistent bat, he’s also learned first base on the fly. In April, I was near positive this guy wouldn’t last in the field for long. Now, I hardly notice him out there — a mark of a solid first baseman.

The MLB Trade Deadline is July 30, and based on years past, it’s likely that how the Cubs perform this week will play into how trade talks are viewed a week and a half from now. I, frankly, am not up for a sell, unless there’s an opportunity to take complete advantage of a World Series-starved team.

That makes these next few games that much more important.

The Cubs aren’t in a good position, but they’re certainly not in an awful one either, all things considered.

I’ll be paying closest attention to Pete Crow-Armstrong coming out of the break. He had two homers in the first-half finale, and he’s a candidate for a breakthrough in the near-term future.

Consider this: He has a 1.2 WAR currently in just 60 games played. But that solid number is not the wild part. The wild part is that he has a 1.2 WAR in 60 games played while he’s batting .203/.253/.329. The other aspects of his game are so good that he’s still a good player, even when he’s not hitting at all.

Now, imagine if he was just hitting at league average? Or, imagine if he got above that?

Any trepidation around PCA thus far has been unwarranted. And I’m ready for him to be the spark plug that helps further turn things around for the Cubbies down the stretch.

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Following the White Sox wire during the course of this season has been completely bewildering. Outside of injury, it’s unclear why they’re ever making the moves that they are making.

Moving on from Martín Maldonado was sensical. The only more sensical route would have been to not sign him in the first place. But, strangely enough, the Sox waited until he had like his five best games in a row to do so. My man had a hit streak going! Maybe I’m missing a key piece of information here, I don’t know.

As far as the trade deadline goes for the Sox, it probably makes sense to trade guys worth a shit given how far they are away from winning.

But, at the same time, guys like Garrett Crochet and Louis Robert are known commodities. Their returns won’t be that. These guys made it through the throes of the White Sox organization and came out good ball players. That should be enough to suggest they’re a couple of the best players in the American League.

You can go ahead and trade them for prospects, but by now, both Cubs and Sox fans should know that “prospects” are a narcotic in the unknown. People love the idea of future potential, but forget the last batch they got gave them a headache and made them uncomfortably hallucinate.

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Basketball season never sleeps at your boy’s place. Not everyone’s idea of a summer day is watching USA and Serbia in a showcase game, and then flipping on the Bulls Warriors in a Las Vegas Summer League showdown later on.

But that’s what we do.

And with that, I’m happy to report on what I’ve seen thus far, with the caveat being that I’ve only watched about 65% of all the summer league minutes your CHICAGO BULLS — led by Billy Donovan Jr. — have played.

First and foremost, what is Dalen Terry doing cheering on the youngins from the sideline like he’s got a $100 million deal? My brother, you need to be in the game boxing out for rebounds and working on a consistent jump shot!

Dalen Terry split minutes with Julian Phillips — the Bulls second-round pick in last year’s draft — last season. Generally, the Bulls favored Terry, which I believed was the wrong decision. It’s most definitely going to be the wrong decision next year, unless Terry miraculously becomes a good basketball player.

Phillips, who is playing in the summer, looks the part. The best part of Summer League is seeing guys who look like they should not be there, in that they look above and beyond the others. Phillips has looked that way at certain points over the last couple of games.

He’s only averaging 11 and 7, but that’s in part because he’s not one of the Summer League players jacking up shots to put a team on notice. He’s not shooting the ball particularly well, but hit stroke looks better than it did at the beginning of last year.

Matas Buzelis — the Bulls first-round pick this year — on the other hand, has been chucking up shots. I’ve enjoyed the aggression, though it has not looked pretty at times. He’s averaging 20 and 5, great numbers for the summer league, and has also had a few highlight-reel dunks over three games.

Buzelis has a great, serious demeanor about him. He almost seems a bit naive, but in a positive way.

Right now, his shot does not look good. The Bulls shooting coach will have to work with him extensively to make him a perimeter threat in years to come. Additionally, he immediately needs to put on 25 pounds. He’s stick thin and it will massively affect his ability to hang in NBA games.

Lastly, he struggles to get to the rim on his own. Improved shooting — to get defenders off balance and coming toward him — and added weight will certainly help in that area.

But right now, he’s a very raw prospect.

All things considered, the Bulls likely have been pleased with his performance thus far. But there are a few things he needs to get way better at, in short order, to become an impact player.

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Thank you so much for reading another newsletter! I appreciate it, as always. See you next week, and comment below.