Still Gotta Come Through Chicago

Is it this easy?

Happy Friday Chicago!

The NFL will enter its free agency period Monday, followed shortly after by the draft.

Before the trees even turn green, a bunch of martians with drool coming out of their mouths talking about the NFL will bloom. The type of people that, if you were in a room alone with them and called them dumb, they’d look around to see who you were talking to.

During this time, it is imperative the Bears address their offensive and defensive lines, but also imperative that you avoid these people. These people who care about the NFL enough to talk about it nonstop, but not enough to understand how it works.

They are among a special class in society.

Among that special class:

— No-longer-young-adults who still say “adulting is hard” at work — you will absolutely end up with a higher workload as they find a way, each day, to explain how hard life was for them in the prior day (they had a tough time sleeping)

— A friend who only has a rudimentary understanding of monetary systems, but loves crypto coins

— A polarized political friend the night after a debate (they didn’t let his or her candidate speak enough)

— Someone who has picked up religion later in life and thinks their way of grappling with that DUI is the way forward for everyone

But the NFL offseason may breed worse conversationalists in 2025 than even religious and political zealots.

Perhaps it’s a sign of downfall in society, that politics and religion is no longer what makes people chatty. Perhaps it’s a sign of progress in American society, that things are so good that people who would at one time be handing out political or religious pamphlets on street corners now concern themselves with the best wide receivers available.

Either way, if I were tasked with turning a sane man insane, I would sit him down with three dumb NFL fans in March and April.

This time of year always brings back me to high school, when a classmate ready for fraternity life in dress, but not yet in age, said that the Bears “should pick up The Gronk.”

The Gronk, of course, referring to the best tight end in the league at the time, Rob Gronkowski, who was under contract and certainly not in trade talks.

Years later and, strangely, an NFL front office has still not hired that man.

It’s mostly easy to spot the person to stay away from. If they mention anyone that played well for their fantasy team in years past as a target for the Bears — Davante Adams, Tee Higgins, Cooper Kupp — run.

But even the novice has become more elevated as the NFL has completely taken over the American sports limelight. These same types are harder to identify, because they may mention the best offensive lineman available, one they saw in an article they glanced at while on the toilet titled “Best Free Agents Available in 2025.” They clicked out when yet another advertisement popped up and their phone stopped allowing them to easily scroll Yahoo.com.

Anyone can talk football, and it’s not my job to gatekeep. I don’t consider myself an expert.

But if you watched the Bears last season and decided that they were an Ashton Jeanty or Tee Higgins away from a playoff run, I’d just rather not waste the precious minutes of my day with you.

Saying “adulting is hard” is an affront to every single one of your ancestors, but hey, it’s harder to maintain the basic responsibilities of an adult than it is to understand that fantasy football success and real football success have almost no relation to each other.

I don’t blame fantasy football for this. I talked to the guy who started it last night and he told me, “Well, I did purposely put the word fantasy in there.” It’s a fair point.

The lines being blurred between the two is why I’ve come to borderline despise — through no fault of its own — fantasy football. And, to some extent, this time of year. It’s when everyone knows best what their favorite team needs to do next — including, I’m embarrassed to say, me.

And unfortunately I still love to watch the NFL Draft.

Last year, at a bachelor party, my friends and I spent the entire first night watching the draft live, swearing not to tip each other off on the picks being tweeted out through our phones before they were made on the TV.

Also unfortunately — it was a riot.

That is, until the bachelor’s mom stopped by to drop off his younger brother and say hello. There we were, many miles from home, still just drinking beer and watching football (and not even football). It was the first time in my life where I wished someone had a bag of cocaine to lay out on the table. Anything to make us look less like losers than we did right then. Someone please tell her strippers are on their way.

But if I ever become the first person to suggest the Bears trade for the next disgruntled superstar running back or wide receiver who wants out of his current situation, or ever begin writing about fantasy football pickups, just know something has gone seriously awry.

You’re more likely to see Daniel Day-Lewis hawking Progressive Insurance next to Flo on your television during March Madness than you are to see me yearning for the best wide receivers available to come to Chicago.

Your dumbest friend will shine during this period, so hold your less dumb friends closely. Otherwise, things can get lonely.

Heralding offensive line trades and looking for a center is not as fun as watching Amari Cooper highlights from two presidencies ago in your spare time. But heavy is the head that wears the crown.

Just like becoming obsessed with the Punic Wars or the 1979-1980 Portland Trail Blazers through literary adventures can be isolating, so can being an NFL fan with a brain.

But it’s also part of becoming an American adult. It’s why Donyell Marhsall was one of my favorite Bulls ever before my prefrontal cortex began to develop.

Instead of winning friends and influencing people, the best advice I can give is to lose friends and stop trying to influence people who can’t be reasoned with. This is the time of year to go to the bathroom a lot and find new conversations. The time of year for “mmhmm”s and “yeah, maybe”s.

Ironically, the “adulting is hard” crowd and the “let’s go get Tee Higgins” crowd are sitting squarely in the same purgatory. To get to the other side, they just need to stop saying the things they are saying.

If you stop saying “adulting is hard,” it will become less hard. And if you stop saying, “let’s go get Tee Higgins,” you will some day look back and realize that is the point where you became an adult.

There’s many rites of passage in life. Quinceañeras, communions, bar mitzvahs. And, in 21st century America, there’s seeing a good player became available, nodding, and letting it alone.

There’s wanting good things in life, and then there’s knowing what’s obtainable. Deciphering between the two will do you a lot of good. Put another way, you should stop liking every one of Sydney Sweeney’s Instagram posts.

As the Bears set out to become a better team than they were last year this March and April, let’s also set out to become better versions of ourselves.

And let’s get into it.

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Just as I finished writing the above, Trey Hendrickson has been granted permission to seek a trade. And now I’m off to get some beers with the martians.

Things have never come easy to the Bears. So what is going on?

Over the past month and a half, things almost seem to be coming too easy. Either it’s not this easy and at least some of these acquisitions (coaches and players) will fail, or it could have been this easy the whole time and this time period is shining further light on their (former?) incompetence.

After hiring the hottest name on the coaching market, and then hiring a dream-team coaching staff around him, the Bears look well on their way to fixing their greatest weakness over the past half decade: the offensive line.

Is it this easy?

September will tell better than March will, but there’s a greater than 50% chance that the Bears will enter next season with a Quarterback (capital Q), Coach (capital C), and Offensive Line (Capital O and L).

For now, the idea of that — however likely — is still too much for me to fully digest.

The Bears didn’t wait for free agency to kick off next week, instead opting to target offensive guards on the trade market.

First came Jonah Jackson, a 28-year-old offensive lineman with a Pro Bowl appearance under his belt. Without the hindsight bias of the Joe Thuney trade a day after, this seemed like a 1) a high upside deal, with the Bears only giving away a sixth-round pick 2) a risky deal, but only from a narrative perspective.

After all, the last time Ryan Poles went after a pricey guard leaving a team willing to part ways with him, the Nate Davis era began in Chicago.

That’s not to say Jackson and Davis are similar players or similar people. It’s just pointing to the fact that Poles will have to earn some trust back with his transactions on the offensive line, whether fair or not.

Jackson played his first four years in Detroit, and played well, becoming a key cog in the line that catapulted the Lions to relevancy in 2023. As mentioned above, he made a Pro Bowl while there, and then earned a three year, $51 million deal with the Rams.

His time in Los Angeles soured due to a shoulder injury, which had him playing from behind. He missed most of training camp and then only played in four games, a bit at each guard positions and at center.

He’s a talented player worth taking a gamble on. Gamble is probably too strong of a word, too. He’ll make $17 million next year (the Bears still have about $43 million of effective cap space, per Over The Cap), but then they can cut ties with him after next year if things don’t pan out — with zero dead money on the books. If he plays well, as he has in the past, the Bears can pay him another $17 million in 2026.

At this point, that is about the going rate for a good offensive lineman, and the cap has continued to skyrocket. The rest of the Bears line also remains relatively young and cheap. They have to eventually use that cap space that we’ve been talking about for two years now.

The question is not whether the 28-year-old can be productive, but more so whether he can stay on the field. He played every game in his first two years, and then missed multiple in the next two years. Last year, of course, he missed the majority of the season.

This, and the Thuney trade, suggest to me that the Bears are not all that impressed with the free agent offensive linemen class.

It also inspires confidence that this is a guy that Johnson worked with for four years, someone who he has belief in and a relationship with. In that sense, this isn’t at all like Nate Davis.

Then there’s trading a fourth-round pick for Joe Thuney, which has only left me with the words “home run.” Thuney has been an star guard in the NFL for 10 years, and he didn’t even cost the Bears a Day 1 or Day 2 draft pick.

Thuney is not just a great lineman. Sitting here, from Chicago, as a Bears fan, he’s basically an alien.

He’s a four-time Super Bowl Champion, winning with the Chiefs and the Patriots. He’s a three-time Pro Bowler, a two-time first-team All-Pro (over the last two years), and a two-time second-team all-pro.

Thuney would mean a hell of a lot to any team he played for, and meant a hell of a lot to the Chiefs and the Patriots. Tom Brady ranked him fourth on his offensive player of the year ballot last year, if you need a sense about how the GOAT feels about him.

But he arguably will mean more to the Bears than any other NFL team he could have played for in 2025.

He’s blocked on some of the best teams of this century, and has blocked for two of the greatest quarterbacks of all time.

Even outside of what he’ll mean to the physical offensive line of the Bears, he’ll be the first real, meaningful voice in that room in a long, long time. That alone, in my opinion, is worth the pick.

While Jackson is likely to be a monster in the run game, Thuney has the highest pass block win rate (97.8%) in the NFL over the past two seasons, according to ESPN’s Courtney Cronin. He logged just one penalty in 2024, per PFF.

Thuney is 32, but is also fresh off his best football. Offensive linemen also age more gracefully than any other position group, with many of the best ones playing well into their late 30s.

The Bears now have their lynchpin of the line. The prospects of Braxton Jones and Darnell Wright already look more hopeful today than they did yesterday.

Next up: Center. Whether that’s Drew Dalman, the former Atlanta Falcons center and free agent, or someone else, I don’t know. If it is Dalman, the Bears will officially have a capitalized Offensive Line. And they can get there without him. Heading into free agency and the draft, the Bears already have a much clearer picture of team needs.

The Bears also replaced Gerald Everett with tight end Durham Smythe, who played his last seven years in Miami. Smythe will be better than Everett if he lines up correctly and moves after the ball is snapped, but he also appears to be a Johnson target.

Within Johnson’s offense, Cole Kmet (if he’s up for it) is likely to be a larger focal point. The second tight end needs to be able to block, and by all accounts, Smythe can do that. Don’t pick him up in your fantasy draft, though.

Between now and next week, the Bears could make a big move for Trey Hendrickson or Dalman. They could mostly stand pat and wait until the draft to fill out the rest of their holes.

Whichever way we go, I’m excited to come back next week and break it down. And, yes, we’ll eventually get to whether or not we should draft Ashton Jeanty (we should not).

Jack Sanborn is also no longer a Bear. All I can say is this, Jack. We all wish it was Tremaine Edmunds.

#BEARDOWN

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CHGO reported this week that the vast majority of limited partners who were offered to be bought out by Justin Ishbia last week took him up on the deal, which is not yet finalized.

In essence, Ishbia is now next in line to own the White Sox. Now, we wait to see when Reinsdorf will opt out.

Whether that’s this year, next year, or five years from now, I don’t know.

But as I wrote last week, I’d expect it to be sooner rather than later. And, make no mistake about it, that will become one of the biggest Chicago sports stories of the 2020s.

Plus, it gives me a reason to write about the White Sox in 2025.

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The Cubs’ hubris is coming back to bite them as they count pennies and talk about their “budget.”

Comcast has, according to the Sun-Times, bumped Marquee Sports Network off their basic tier and into their high-price tier. That means that they’ll likely get paid more for the subscribers they do have at Comcast, but that they’ll have a lot less of them.

The Cubs decided to cut off a great deal of their fanbase from watching their games when they launched Marquee, and promised it would be a cash cow that would result in more money going into the players.

Needless to say, that has not happened.

Now, a non-cash cow has become even less of one. For those of us that do watch the Cubs night in, night out, things mostly won’t change. If you have Comcast, there’s a good chance you already pay for the higher-price tier. I personally pay directly for Marquee, and am unable to go between channels during the games.

As I once suspected, the Marquee Sports Network (with dreadful pre- and post-game shows) has resulted in more money coming out of our pockets, but not any more money going on the field.

All the while, White Sox fans are left with this: The Sox are “hopeful” that Comcast will pick their Chicago Sports Network up for the baseball season. After all, Chicagoland is oh so excited for the baseball season the South Side.

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The Bulls still have no plan and keep winning games. They are now three games up on the next-best (or worst) team in the standings. They are firmly in the 10th seed, and beat the Magic last night.

They will, in all likelihood, be playing in the play-in game for the third straight year—ensuring they stay firmly in purgatory.

But, hey, at least Coby White went for 44 last night, and at least Tre Jones, Kevin Huerter, and Zach Collins — who came over in the LaVine trade — have showed some promise over the last dozen games.

Will Arturas Karnisovas harness that promise and deal them when he should next year? Extensions are more likely.

LETS GO BULLS!

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Thank you for reading another newsletter. As always, I appreciate it. And as always, tell someone to subscribe up top today! Comment below, whether you’re an excited Bears fan, a hopeful Sox fan, or an angry Cubs or Bulls fan.