Judging the results of a team’s MLB draft shortly thereafter is a fool’s errand. Giving out “draft grades” or describing which team “won the draft” has little merit when it’s done only a few months afterwards. You want to look at drafts three years later, or even better five to six years later to truly evaluate the successes and failures of in the selections. It’s also fair to point out early successes.

The Chicago Cubs could point to several names like Matt Shaw, Josh Rivera, Brett Bateman, Jonathon Long, Zyhir Hope, Brian Kalmer as players who took to pro ball quickly and are producing. Internally there is optimism on Jaxon Wiggins among many others on the pitching side. We’ll need to properly evaluate the class several years later, but early returns suggest it could be another strong class.

This points to an encouraging trend as the Cubs have produced talent even outside the first round in each of the past four drafts. The 2024 draft class will hope to continue that trend.

But before we move past 2023, let’s explore the path untraveled. What if we at North Side Bound made the selections knowing what we know now based on who would sign and for what bonus? Introducing the 2023 Chicago Cubs Shadow Draft.

What is a Shadow Draft?

A shadow draft is fairly common in the blogosphere. It’s a thought-piece where draft fans make their picks after the fact about who they’d have taken for their respective team. To run our shadow draft I had to follow a few simple rules:

  • The player taken at a certain pick had to be available when that selection was made. We couldn’t “buy down” a player. So, for instance, the Cubs (in this exercise) couldn’t offer Brock Vradenburg an extra $250k to go at pick 81 when he was really taken at pick 78
  • The player had to receive a minimum of the signing bonus they signed for in the 2023 draft
  • Draft rules had to apply so with pick 1, 13th overall, that player was believed to be eligible for a minimum signing bonus of 75% of slot.
  • And let’s have some fun with this, so just taking all the same players the Cubs made is lame.

Let’s get to the picks.

First round (13) – Colt Emerson – SS – John Glenn (HS), OH

13th pick slot value: $4,848,500
Actual 2023 signing info: 1st round (22) by SEA; $3,800,000
Projected bonus value: $4,000,000

How the Cubs draft: We saw the Cubs prioritize players who the organization viewed as falling to them in Howard and Wicks. However, unless something baffling happened last year, they were into Cade Horton’s profile. This is an organization that has been willing to target upside with their top few selections over the past few years.

Emerson entered the season as a top ten overall prospect in my draft ranking and he’s made that ranking hold up. Emerson possesses one of the best hit tools in the high school class, which is a critical component into how evaluate hitters, especially prep players. I have been impressed with Emerson’s actions at shortstop and believe he plays the position at the next level. The real question from some is how much power does Emerson get to in the pros? But I don’t buy into that concern as he has shown he can get to power, and he only recently turned 18 (after the MLB Draft). To me, Colt Emerson gives off Jake Cronenworth vibes. I’m very in on him.

Why not Matt Shaw?
Because it’s not as fun to go “chalk”. Shaw is outstanding. He’s a dynamite selection, but where would the fun be if I just picked the same players as Dan Kantrovitz and company did? I mocked Emerson to the Cubs on draft day and I’ll stick with him here.

Second Round comp (68) – Cade Kuehler – RHP – Campbell

68th pick slot value: $1,101,000
Actual 2023 signing info: 2nd round comp (70) by ATL; $1,050,000
Projected bonus value: $1,101,000

I entered 2023’s draft cycle with Cade Kuehler in at least consideration for my second ranked SP in the class. Ultimately, he didn’t take as big of a step forward as I was projecting, but his improvements were noticeable. The stuff is real and while it’s more below average command; I believe the profile in pro ball will work. Kuehler for slot was a great value, in my mind.

Why not Jaxon Wiggins?
There will be some in the Cubs organization that would (or maybe still will) message to say that I’m crazy for passing Wiggins up. He has some believers in the organization. I’m excited to see it too, but I really love Kuehler for the value at slot because it allows me to go big in round 3 by taking…

Third Round (81) – Brandon Winokur – OF – Porter (HS), TX

81st pick slot value: $872,400
Actual 2023 signing info: 3rd round (82) by MIN; $1,500,000
Projected bonus value: $1,500,000

Winokur had a huge showing at the MLB Draft combine, but scouts saw his potential well before that event. It’s a toolsy package that looks like it’s all coalescing. The UCLA commit, Winokur, required a significant bonus to buy him out of college. Taking him in this draft represents another huge potential player.

Why didn’t I select Josh Rivera?
Rivera was my favorite selection of the entire class, so why didn’t I take him again? As I was building out this draft class, I wanted to balance risk and upside. After the third round, I struggled with the ability to find those high potential players which forced me to go heavy into the college ranks. Ultimately my choice was missing out on Winokur or to swing for the upside early. A path I considered was taking a later player like Cooper Pratt (overslot sixth round to MIL) or George Wolkow (overslot seventh round to CWS). I liked Winokur’s profile better than either option. It meant I lost out on Josh Rivera, which wasn’t ideal, but I liked the overall profile of what I built in this class better than those other options.

Similar to how the Cubs structured their draft, I targeted college performers with my next several selections. This hedges against the risk from picks in the first and third round and just finding value from a deep class of college players.

Fourth Round (113) – Jake Cunningham – CF – Charlotte

113th pick slot value: $591,800
Actual 2023 signing info: 5th round (154) by BAL; $375,000
Projected bonus value: $400,000

This draft featured an intriguing set of Day 2 college centerfielders like Carson Roccaforte, Tavian Josenberger, and Cunningham. I knew I wanted to end up with one of them. Cunningham combined the best combination of barrel rate, which the Cubs emphasized n this draft, and signing bonus. I feel like this is strong value at this stage of the draft.

Fifth Round (149) – Michael Carico – C – Davidson

149th pick slot value: $416,900
Projected/Actual bonus value: $416,900

Loved the selection on the day of the draft. Carico’s larger impact should come in 2024 after he’s had an entire offseason of rest, recovery, and instruction. His batted ball profile is one of my favorites with a heavy emphasis on contact and not chasing the ball.

Sixth Round (179) – TJ Nichols – Arizona

176th pick slot value: $325,600
Actual 2023 signing info: 6th round (183) by TBR; $304,800
Projected bonus value: $325,600

The stats are ugly (8.27 ERA), but my goodness are the ingredients with his fastball/slider exciting. It’s a mid 90s+ fastball with ride that eats up hitters. He generated approximately 35% swing and miss on his slider. It’s possible Nichols is a relief prospect long term, but I’d give him a chance to start after an offseason working on performance science.

Had Oral Roberts’ RHP Cade Denton made it to here, I would have taken him for $500k.

Seventh Round (209) – Jacob Bresnahan – LHP – Sumner (HS), WA

206th pick slot value: $254,500
Actual 2023 signing info: 13th round (398) by CLE; $375,000
Projected bonus value: $400,000

Bit of a deep cut here, but this is a Pacific NW arm to watch over the course of the next few seasons. Bresnahan has a strong changeup and topped out in the low 90s. He looks like a candidate to add velocity and struggles to land a consistent breaking ball. Those are both areas where I’d feel good about the Cubs chances in helping him improve.

Eighth Round (239) – Ross Dunn – LHP – Arizona St

236th pick slot value: $203,600
Actual 2023 signing info: 10th round (297) by MIN; $150,000
Projected bonus value: $203,600

Dunn was one of my favorite deep-cut arms in the class. He shows off a low 90s fastball, but touches higher. He gets swing and miss on multiple pitches. His downfall is command, but late on Day 2, I’m willing to gamble on the upside. If he has to move to the pen, there is still value there this late.

Ninth Round (269) – Jonathon Long – 1B – Long Beach

266th pick slot value: $179,400
Projected/Actual bonus value: $179,400

There is no way I’d have gone in another direction. While this (and the Hope/Kalmer selections) benefit from hindsight, Long deserves a repeat selection. He was immediately a player who some reached out to confirm that he gets to the barrel easily. We’ve seen that continue in pro ball. He is a strong candidate to end 2024 in AA.

Tenth Round (299) – Brett Banks – RHP – UNC Wilmington

296th pick slot value: $168,300
Actual 2023 signing info: 11th round (336) by NYM; $200,000
Projected bonus value: $200,000

The skinny: Impact college reliever who regularly popped on Stuff+ models. He shows a fastball in the upper 90s with good ride and a swing and miss slider. His command held him back, and it remains to be seen how it will progress in the pros. In the tenth round, this was an easy decision.

Day 3 is for dreamers and the Cubs landed dream scenarios in rounds 11-20. I ultimately stayed with many of those selections. Rounds 13 and 16 both offered the chance to take players I was high on prior to the draft.

Round 11 – Zyhir Hope – OF – Colonial Forge (HS), VA

Projected/Actual bonus value: $400,000

“Z” has been amazing to follow. The raw tools are there to be an impact player. He has considerable work to do t address swing and miss, but I’m not concerned until next season. Give Hope a full offseason working with pro instruction.

Round 12 – Josh Tiedemann – 3B – Hamilton (HS), AZ

Actual 2023 signing info: 13th round (402) by NYY; $150,000
Projected bonus value: $150,000

Perhaps this is just amazing background work by the NY scouts or Tiedemann was dead set on playing for the Yankees. New York signing Tiedemann for Day 3 slot shocked me. As the high school teammate for Roch Cholowosky, Tiedemann had a lot of eyes on him this spring. He didn’t show out, but still shows tools on both sides as both a hitter and pitcher. I am intrigued by Day 3 swings on high school players. While I like Trice and almost kept him here, I’d have been willing to take a chance on Tiedemann for Day 3 slot money.

Round 13 – Brett Wichrowski- RHP – Bryant

Actual 2023 signing info: 13th round (392) by MIL; $100,000
Projected bonus value: $100,000

Wichrowski had a solid year for Bryant Baseball, but he’s succeeding on the Cape showcasing some swing and miss. The slider, in particular, displays sweep and could play up in the bullpen.

Round 14 – Grayson Moore – RHP – Vanderbilt

Projected/Actual bonus value: $150,000

Round 15 – Ty Johnson – RHP – Ball State

Projected/Actual bonus value: $125,000

Round 16 – Josh Timmerman – RHP – Ohio State

Actual 2023 signing info: 16th round (482) by MIL; $150,000
Projected bonus value: $150,000

Timmerman’s 2023 numbers aren’t pretty (8.75 ERA, 7.6 BB/9), but he’s been electric on the Cape Cod League, generating Ks and limiting walks. The building blocks are there for a pro pitcher who can develop in the pitch lab.

I assure you I didn’t just take Josh Timmerman because I took Josh Tiedermann above, but how fun would that be in the future?

Rounds 17-20: I stayed with the selections the Cubs made this past July. It’s hard to argue with any, but especially Brian Kalmer. That was a home run selection in every sense of the phrase. It wouldn’t surprise to see Kalmer finish 2024 in AA or even AAA. Flanagan and Bowser offer intrigue. Dean will be a guy to watch after spending time in the lab this wnter.

Round 17 – Ethan Flanagan – LHP – UCLA

Projected/Actual bonus value: $150,000

Round 18 – Brian Kalmer – 3B – Gonzaga

Projected/Actual bonus value: $50,000

Round 19 – Nick Dean – RHP – Maryland

Projected/Actual bonus value: $75,000

At this stage in the draft, I didn’t have any other signed players that I would have gone with over who the Cubs selected. Best to roll with one of the best scouts in the business, Billy Swoope, and trust his evaluation of Nick Dean. Drew Bowser for Day 3 slot was also an inspired selection.

Round 20 – Drew Bowser – 3B – Stanford

Projected/Actual bonus value: $150,000

There you have it! The entire 20-round draft, as I would have taken them. There are a lot of familiar names and it’s hard to argue with who the Cubs actually selected this past summer, but this was a fun exercise in “What-ifs”

What would your strategy be?

I mixed upside and safer profiles while trying my best to guess about signability. That can be a fools errand, but it attempts to mirror the complexity that teams face when they build their boards.

How would you build your ideal Cubs draft? Is there a player you’d “pound the table” in the draft room for?