2025 MLB Draft Day 2 Thread: Chicago Cubs Draft on North Side Baseball

[Brandon Glick]

Image courtesy of © Brett Davis-Imagn Images

The 2025 MLB Draft will again feature just 20 rounds, but there has been a format change. After downsizing from a two-day, 40-round draft to a three-day, 20-round draft, Major League Baseball has now gone to a two-day, 20-round draft. 

The final 17 rounds (from Rounds 4-20) will happen later today, beginning at 11:30am EST. You can catch it live on MLB Network and MLB.com. The Destination: The Show crew would like to invite you to join us live as we cover the final rounds of the draft There hasn't been a 17-round draft day in a while, but rest assured — there used to be 20-round days, so North Side Baseball will have the capacity to cover the duration.

After selecting three players on Sunday during the first day of the draft, the Cubs will make 17 picks on Monday:

121st Overall (Round 4)

151st Overall (Round 5)

181st Overall (Round 6)
Following Round 5, the Cubs will pick 16th in every round for the remainder of the draft.
Thus, their draft position is as follows: 181, 211, 241, 271, etc.

The Red Sox will have the 13th-largest bonus pool ($12,409,300) in baseball. As a reminder from Baseball America: "In the MLB draft, each pick inside the first 10 rounds comes with assigned slot values. The sum of those slot values creates each team’s bonus pool. From rounds 11-20, players can sign for up to $150,000 without counting towards the bonus pool. Anything beyond that value does count towards the pool."

It's also important to remember that teams can exceed their bonus pool allotment by up to five percent before incurring any future pick penalties. No team in bonus pool era has ever exceeded that additional five percent threshold.

Once again, North Side Baseball will feature the Cubs Draft Tracker, which will be kept up-to-date not only during the draft but through the entire signing period. So keep coming back for updates!

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[nochiinchamp]

I wonder how aggressive they'll be with Kepley. Seems like the low minors are exactly the place where he just won't be challenged in a meaningful way since offensive profile is basically all OBP.

[Bertz]

27 minutes ago, nochiinchamp said:

I wonder how aggressive they'll be with Kepley. Seems like the low minors are exactly the place where he just won't be challenged in a meaningful way since offensive profile is basically all OBP.

I'd guess fairly aggressive.  Myrtle Beach has been kind of a disaster this season and is not prepared to graduate much talent up the system on moving day in a few weeks after the deadline.  So there's not anyone really blocking Kepley from getting to South Bend within the next month.

[Stratos]

If Kepley is a sure CF you wonder if he'll be traded at some point because of being blocked by PCA,

[Rcal10]

What big swings can the Cubs take? I mean, are there really guys available who are worth giving 2nd round money to, drafted in round 4 thru 7. And, if so, why weren’t they drafted already? Is a gig time HS guy going to opt out of a college xommitment for 2nd rd money? 

[vance_the_cubs_fan]

I am just hoping to see my student William Patrick taken early today. We were hoping he would go third round, but it didn't happen. He's a good kid and will go to LSU if not taken, but I know he's wanting to go. 

[nochiinchamp]

18 minutes ago, Stratos said:

If Kepley is a sure CF you wonder if he'll be traded at some point because of being blocked by PCA,

He doesn't seem like the kind of guy who'd develop tremendous trade value or anything. Maybe he could help get them a good bullpen arm eventually? But I think they just want on-base skills and CF defense in the system and ready to contribute soon.

[Outshined_One]

12 minutes ago, Rcal10 said:

What big swings can the Cubs take? I mean, are there really guys available who are worth giving 2nd round money to, drafted in round 4 thru 7. And, if so, why weren’t they drafted already? Is a gig time HS guy going to opt out of a college xommitment for 2nd rd money? 

The short answer is, there is a lot of fuzzy accounting that happens in the MLB Draft.  Teams have bonus pools which they can allocate, and MLB places penalties on teams on a sliding scale based on how far over a team goes.  On the flipside of the equation, HS players now have a fair amount of leverage thanks to NIL, so there's not a lot of risk for guys to ask for significant signing bonuses.

Make no mistake, the overwhelming majority of HS guys rated as first round picks will get drafted in the first round and will sign.  However, where things get squishy is when you start seeing guys making first round demands who maybe aren't rated that high.  So, what a team might end up doing is draft a bunch of guys who'll sign underslot, and then take one of those guys with, say, a 6th round pick and offer him a substantial bonus.  If he signs, awesome.  If he doesn't, it's not as big of a loss compared with drafting him with a 2nd rounder and losing that pick.

There's a good crop of high ceiling HS pitching still available, including Chicago area pitchers LHP Jack Bauer (Lincoln Way East) and LHP Cameron Appenzeller (Glenwood HS).

[Outshined_One]

Turley off the board.  The A's have had a low key really good draft so far.

[Hrubes20]

Briggs McKenzie, please

[Hrubes20]

Just now, Outshined_One said:

Turley off the board.  The A's have had a low key really good draft so far.

I’m a fan of that draft

[CaliforniaRaisin]

13 minutes ago, Outshined_One said:

The short answer is, there is a lot of fuzzy accounting that happens in the MLB Draft.  Teams have bonus pools which they can allocate, and MLB places penalties on teams on a sliding scale based on how far over a team goes.  On the flipside of the equation, HS players now have a fair amount of leverage thanks to NIL, so there's not a lot of risk for guys to ask for significant signing bonuses.

Make no mistake, the overwhelming majority of HS guys rated as first round picks will get drafted in the first round and will sign.  However, where things get squishy is when you start seeing guys making first round demands who maybe aren't rated that high.  So, what a team might end up doing is draft a bunch of guys who'll sign underslot, and then take one of those guys with, say, a 6th round pick and offer him a substantial bonus.  If he signs, awesome.  If he doesn't, it's not as big of a loss compared with drafting him with a 2nd rounder and losing that pick.

There's a good crop of high ceiling HS pitching still available, including Chicago area pitchers LHP Jack Bauer (Lincoln Way East) and LHP Cameron Appenzeller (Glenwood HS).

All of this is well said but I will add to that the bold seems to no longer be accurate for prep pitchers rated as first round values unless they are Seth Hernandez-level talents. Teams "float" most of the 15-50th rated prep pitchers to later rounds because of the additional risk of prep pitchers (so they can take safer guys earlier). As you noted, these kids can still get late first round money.

[CaliforniaRaisin]

5 minutes ago, Outshined_One said:

Turley off the board.  The A's have had a low key really good draft so far.

On the heels of having a fantastic, college-heavy draft last year too.

[CaliforniaRaisin]

Cubs select: RHP Kaleb Wing, Scotts Valley HS (CA) - Loyola Marymount (CA) commit

[Outshined_One]

That's more like it.

[CaliforniaRaisin]

MLB Pipeline ranks Wing 121st: 

Quote

Back in 2001, Ryan Wing was a second-round pick of the Chicago White Sox out of Riverside City College, a two-year school outside of Los Angeles. The left-handed pitcher spent seven seasons in pro ball, topping out at the Triple-A level in the A's organization. Now it's his son Kaleb's turn as a two-way player from the northern California high school ranks, a defensive-minded shortstop who appeared to be turning a corner this spring as a right-hander with an uptick in stuff, allowing him to move up boards. Wing doesn't have a ton of history on the mound, but appeared to be figuring things out in a hurry during his senior season. The athletic 6-foot-2 righty made the Area Code Games as a backup arm and was mostly around 88-90 mph with a big loopy overhand curve. This spring he came out of the gate showing a fastball up to 95 mph and hasn't backed off from those gains. His curve now flashes plus as a power breaker with depth, and his changeup is developing into a solid third offering. Wing's athleticism helps him repeat his delivery and find the strike zone consistently. There's a little concern about how much strength he'll be able to add to his narrow frame, but the uptick in stuff across the board could have teams interested in signing him away from his commitment to Loyola Marymount, where he had originally planned to both pitch and hit.

 

[CaliforniaRaisin]

BA ranks him 201st: 

Quote

201. Kaleb Wing

RHP

Ht: 6'2" | Wt: 175 | B-T: R-R

School: Scotts Valley (Calif.) HS Drafted/Committed: Loyola Marymount
Age At Draft: 18.5

Wing is a 6-foot-2, 175-pound righthander who showed fine stuff and projection during the 2024 travel circuit, then made a strong step forward during his 2025 spring season. After sitting in the upper 80s and topping out around 90 mph at the 2024 Area Code Games, Wing pushed his fastball up to 95 mph and was more consistently averaging 92-93 during the 2025 spring—a notable uptick. He shows the makings of a four-pitch mix, but needs to continue refining his release point and his feel to land all three of his secondaries. Wing has tended to prioritize a mid-70s curveball with top-down shape and solid depth as his go-to breaking ball, but he will also flash a harder slider in the low-to-mid 80s. Against lefties, he has also shown a willingness to break out a changeup in the low 80s. Wing is a good mover on the mound and features a bit of a coil and tilt in his leg lift before firing to the plate from a three-quarters slot with good direction and balance. After his senior season, he pitched in the collegiate West Coast League. He’s committed to Loyola Marymount and fits in rounds 5-10 on talent.

 

[craig]

39 minutes ago, Rcal10 said:

What big swings can the Cubs take? I mean, are there really guys available who are worth giving 2nd round money to, drafted in round 4 thru 7. And, if so, why weren’t they drafted already? Is a gig time HS guy going to opt out of a college xommitment for 2nd rd money? 

I think more modest swings than "big" swings.  Kantro has gone overslot on Gray, Paciolla, Mule; Zyhir HOpe; Melendez; Rosario; Lovich; Southisene.,  Obviously none of these were "big" swings, like 1st-round-type guys.  But a lot of good talent if you can scout wisely.  

[Bertz]

Fun!  We need more projectable pitching at the lowest levels.

[CaliforniaRaisin]

ESPN/Kiley had him ranked 95th.

[Outshined_One]

Athletic high upside HS arm with limited mileage, promising offspeed stuff, and comes from a baseball family.

All good things!

[CaliforniaRaisin]

3 minutes ago, craig said:

I think more modest swings than "big" swings.  Kantro has gone overslot on Gray, Paciolla, Mule; Zyhir HOpe; Melendez; Rosario; Lovich; Southisene.,  Obviously none of these were "big" swings, like 1st-round-type guys.  But a lot of good talent if you can scout wisely.  

But he also took Jackson Ferris (top 25 bonus in his draft year) the last time he went as far underslot as Greg Z assumes Conrad will be.

(But Wing is probably more in the Southisene/Mulé low 7-figures bonus area.)

[Cubs420psd]

More of this today plz

 

[Hrubes20]

5 minutes ago, CaliforniaRaisin said:

MLB Pipeline ranks Wing 121st: 

 

They had him 87th

[CaliforniaRaisin]

Just now, Hrubes20 said:

They had him 87th

Oops, you're right. 121st pick.