Format = Position Player | Age on 4/1/2026 | Highest Level Played | Estimated Time of Arrival
1. C Moises Ballesteros | 22 | MLB | 2025
A left-handed hitter listed at 5’8” 215 lbs, Ballesteros puts barrel to ball with the best of them, making contact just about any time he feels like it and minimizing strikeouts every step of his climb to the precipice. In 114 Triple-A games this year, he slashed .316/.385/.473 with 13 home runs and just 67 strikeouts against 49 walks. His bat has outpaced his defensive development, so even though he’s always generated positive outcomes against much older competitors, Ballesteros might have to make a leap behind the plate or wait while the Cubs sort through other options at his position.
2. OF Owen Caissie | 23 | MLB | 2025
Listed at 6’3” 190 pounds, Caissie brings double-plus power from the left side as a hitter. He looks bigger than that to me, but it’s pretty common for teams to measure a guy on signing day and leave it alone for a long time after that. A right-handed throwing corner outfielder, Caissie will have to hit quite a bit to sustain an everyday job for any team, and it’s kind of hard to imagine he can clear the bar for a team with a budget as big as the Cubs’, who probably should have traded him at the deadline for a pitcher like Sandy Alcantara or Edward Cabrera. In 99 Triple-A games, Caissie slashed .286/.386/.551 with 22 home runs and 121 strikeouts (27.9%). That’s just on the line, contact wise, but Caissie hits the ball hard enough to blur that hurdle, even if he might wind up a streaky platoon type.
3. RHP Jaxon Wiggins | 24 | AAA | 2026
Wiggins, who’s listed 6’6” 225 pounds, turned 24 on October 3. Like a lot of large pitchers, he appears to be really hitting his stride as he enters his mid-20’s, repeating his delivery and maintaining his balance better with each month he spends on a minor league mound. He covered three levels in just 78 innings in 2025, recording 97 strikeouts and allowing a 2.19 ERA and 1.03 WHIP on the strength of a three-pitch mix: fastball, slider, changeup, which gives him weapons against hitters from both sides of the plate. Reports suggested the front office got clingy with Wiggins at the trade deadline this year: likely a good sign for his outlook heading into 2026.
4. OF Kevin Alcantara | 23 | MLB | 2024
There’s certainly a good case or two to be made for the 6’6” 188 pound Alcantara, an athletic marvel who brings above average power, speed and defense to the ballpark. The only thing he hasn’t been able to do on a consistent basis is make solid contact, but that hasn’t stopped him from posting productive outcomes, such as the .266/.349/.470 slash line he produced in 102 Triple-A games this year. He’d have to be better than that, probably, to crack a lineup that should have first-division regulars across the diamond, but perhaps he’ll get moved somewhere with more open pastures this off-season. PS: This guy makes me think we should change Estimated Time of Arrival to Estimated Arrival of Playing Time or something.
5. 1B Jonathan Long | 24 | AAA | 2026
If I’m running the Cubs, I find room for Long this season, probably in a DH/1B platoon with Moises Ballesteros and maybe Owen Caissie, letting Michael Busch face any lefty who isn’t dominant against same-side hitters. I might normally say that’s not going to happen, but the Cubs are pretty cheap despite making a lot more money than they spend on an annual basis, so this could be an easy sell from the front office if that’s a risk they want to take. My thinking would be it’s not that hard to find a positionless bat if that’s what you’re lacking. Long has earned the look by producing at every level, culminating in a slash line of .305/.404/.479 with 20 home runs in 140 Triple-A games this year.
6. SS Jefferson Rojas | 20 | AA | 2027
Like a lot of young guys signed through international channels, Rojas looks a lot thicker than his listed 5’11” 150 pounds, which is fine for our purposes as it amplifies his innate power to all fields. He seems to have maintained his solid contact skills, too, or at least that was the case in High-A before he fell on his face for 39 games in Double-A, sputtering to season’s end with a slash line of .164/.279/.205. It’s a common refrain for a lot of guys. Get promoted, struggle, return to the level after an off-season and thrive. Rojas pulled that same trick with High-A last season, so there’s reason for optimism heading into 2026.
7. OF Ethan Conrad | 21 | NCAA | 2027
The Cubs must love Ethan Conrad because they could’ve just drafted a healthy hitter in his spot but opted for the Wake Forest lefty with upside across his tool set. He’s more of a Marist lefty, to be thorough. He played 103 games there against just 21 at Wake Forest, so the stats don’t tell us much, though he did hit seven home runs in those 21 games. Dominated at Marist, too, of course, but it’s unclear how much those outcomes matter. Lotta known unknowns, is what I’m saying here.
8. SS Cristian Hernandez | 22 | A+ | 2027
A three-million-dollar signing in 2021, Hernandez has taken a long time to get situated as a professional baseballer. He played a season in the Dominican Summer League, then a season on the complex, then almost two full seasons in Low-A before graduating to High-A near the end of the 2024 season. In 115 High-A games this season, he hit seven home runs, stole 52 bases and slashed .252/.329/.365, good for a 97 wRC+. I think that’s good enough that he’ll open 2026 in Double-A, where his easy speed and plate skills should translate well. If he ever ages into the power latent in his 6’2” frame, he’ll be a coveted player in our game.
9. 2B Pedro Ramirez | 22 | AA | 2026
It’s tough to place Ramirez for our purposes because it’s hard to imagine he can earn significant run on this team unless he makes some changes to his game. He’s not a hunter in the box right now, accepting opposite field ground balls and slap hits as positive outcomes because his legs are good enough to steal some hits against minor league defenders. A switch hitter listed at 5’9” 165 pounds, he does have the twitch to pop some dingers if he learns to elevate and pull. He already got eight home runs in 129 Double-A games last year along with 28 steals and a 118 wRC+, so he’s succeeding even as it’s easy to point out things he can improve, which is an encouraging sign.
10. 2B Juan Cabada | 17 | DSL | 2030
Hitting is the easy part for Cabada, who signed for $1.5 million this January and then slashed .287/.429/.426 with three home runs and 20 stolen bases in 42 Dominican Summer League games. A left-handed hitter at 5’10” 165 pounds, Cabada employs a quick, controlled swing and solid plate skills that make him a candidate to rise quickly through the professional ranks.
Thanks for reading!
12 team dynasty 5×5…at SS I have Willie Adames…but to keep him I to drop Colt Emerson or Sebastian Walcott which I don’t want to do…I guess I drop Willie…thoughts and thank you!