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| Monday, June 14th , 2027 |
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| Traded 31-year old 1B Nathaniel Lowe to the Seattle Mariners, getting 25-year old minor league C Corey Collins and 25-year old minor league 1B TJ Curd in return. |
| Monday, June 7th , 2027 |
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| Drafted SP Cloyce Edwards in the 2027 first-year player draft (Round 1, Pick 28, 28th overall pick). |
| Drafted 3B Curt Coker in the 2027 first-year player draft (Supplemental Round 1, Pick 5, 35th overall pick). |
| Drafted SP Luis Fonseca in the 2027 first-year player draft (Round 2, Pick 28, 64th overall pick). |
| Drafted CF Jeremy Doering in the 2027 first-year player draft (Round 4, Pick 28, 118th overall pick). |
| Drafted SP Phil DiCioccio in the 2027 first-year player draft (Round 5, Pick 28, 148th overall pick). |
| Drafted SP Bobby Clark in the 2027 first-year player draft (Round 6, Pick 28, 178th overall pick). |
| Drafted 1B Jared Sisson in the 2027 first-year player draft (Round 7, Pick 28, 208th overall pick). |
| Drafted RF Alex Haase in the 2027 first-year player draft (Round 8, Pick 28, 238th overall pick). |
| Drafted RF Kevin Ackerman in the 2027 first-year player draft (Round 9, Pick 28, 268th overall pick). |
| Drafted CF Tim George in the 2027 first-year player draft (Round 10, Pick 28, 298th overall pick). |
| Drafted C Billy Jones in the 2027 first-year player draft (Round 11, Pick 28, 328th overall pick). |
| Drafted CL Eric Beren in the 2027 first-year player draft (Round 12, Pick 28, 358th overall pick). |
| Drafted 1B Steve Dickenson in the 2027 first-year player draft (Round 13, Pick 28, 388th overall pick). |
| Drafted RF Francis Lemos in the 2027 first-year player draft (Round 14, Pick 28, 418th overall pick). |
| Drafted SP Truman Marleau in the 2027 first-year player draft (Round 15, Pick 28, 448th overall pick). |
| Drafted CL Joe Troilo in the 2027 first-year player draft (Round 16, Pick 28, 478th overall pick). |
| Drafted 1B Joey Avery in the 2027 first-year player draft (Round 17, Pick 28, 508th overall pick). |
| Drafted CF Chase Colar in the 2027 first-year player draft (Round 18, Pick 28, 538th overall pick). |
| Drafted 1B Juan Crespo in the 2027 first-year player draft (Round 19, Pick 28, 568th overall pick). |
| Drafted RP Mike Davis in the 2027 first-year player draft (Round 20, Pick 28, 598th overall pick). |
| Sunday, June 6th , 2027 |
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| Signed international amateur SP Juan Vega out of Dominican Republic to a minor league contract. |
| Tuesday, May 4th , 2027 |
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| Signed international amateur CF Gian-Andrea Mondello out of Venezuela to a minor league contract. |
| Saturday, May 1st , 2027 |
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| SS Sam Mongelli did not elect for free agency and will remain in the Chicago organization. |
| SP Griffin Canning did not elect for free agency and will remain in the Chicago organization. |
| Monday, April 19th , 2027 |
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| Assigned RP Daniel Palencia to Triple A Iowa. |
| Thursday, April 1st , 2027 |
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| Demoted SP Kyle Hurt from Triple A Iowa to Double A Tennessee. |
| Demoted SP Thomas Hatch from Triple A Iowa to Double A Tennessee. |
| Demoted SP Tony Gonsolin from Triple A Iowa to Double A Tennessee. |
| Demoted SP Richard Gallardo from Triple A Iowa to Double A Tennessee. |
| Demoted SP Will Sanders from Triple A Iowa to Double A Tennessee. |
| Demoted SP Griffin Canning from Triple A Iowa to Double A Tennessee. |
| Demoted RP Alfredo Romero from Triple A Iowa to Double A Tennessee. |
| Demoted RP Michell Miliano from Triple A Iowa to Double A Tennessee. |
| Demoted RP Yenrri Rojas from Triple A Iowa to Double A Tennessee. |
| Demoted SP Dean Kremer from Triple A Iowa to Double A Tennessee. |
| Demoted RP Carlos Jimenez from Triple A Iowa to Double A Tennessee. |
| Demoted SP Adrian Houser from Triple A Iowa to Double A Tennessee. |
| Demoted SP Tanner Houck from Triple A Iowa to Double A Tennessee. |
| Demoted SP Porter Hodge from Triple A Iowa to Double A Tennessee. |
| Demoted SP Ben Gross from Triple A Iowa to Double A Tennessee. |
| Demoted SP Josiah Gray from Triple A Iowa to Double A Tennessee. |
| Demoted SP Jack Patterson from Double A Tennessee to High-A South Bend. |
| Demoted RP Jarod Wright from Double A Tennessee to High-A South Bend. |
| Demoted SP Kyle Hurt from Double A Tennessee to High-A South Bend. |
| Demoted SP Zach Hise from Double A Tennessee to High-A South Bend. |
| Demoted SP Thomas Hatch from Double A Tennessee to High-A South Bend. |
| Demoted SP Richard Gallardo from Double A Tennessee to High-A South Bend. |
| Demoted SP Griffin Canning from Double A Tennessee to High-A South Bend. |
| Demoted SP Hayden Wesneski from Double A Tennessee to High-A South Bend. |
| Demoted RP Alfredo Romero from Double A Tennessee to High-A South Bend. |
| Sent SP Luis Martinez-Gomez from High-A South Bend to Class A Myrtle Beach. |
| Sent SP Landon Ginn from High-A South Bend to Class A Myrtle Beach. |
| Sent RP Anthony Mendez from High-A South Bend to Class A Myrtle Beach. |
| Sent SP Drew Gray from High-A South Bend to Class A Myrtle Beach. |
| Promoted RP Luis Rujano from Rookie League Chicago N (ACL) to Class A Myrtle Beach. |
| Promoted RP Jesus Benavides from Rookie League Chicago N (DSL) to Class A Myrtle Beach. |
| Promoted RP Erik Barb from Rookie League Chicago N (DSL) to Class A Myrtle Beach. |
| Demoted SP Luis Martinez-Gomez from Class A Myrtle Beach to Rookie League Chicago N (ACL). |
| Demoted SP Yoendris Gonzalez from Class A Myrtle Beach to Rookie League Chicago N (ACL). |
| Demoted SP Landon Ginn from Class A Myrtle Beach to Rookie League Chicago N (ACL). |
| Demoted SP Garrett Gainous from Class A Myrtle Beach to Rookie League Chicago N (ACL). |
| Demoted SP Jaxon Wiggins from Class A Myrtle Beach to Rookie League Chicago N (ACL). |
| Demoted SP Aaron Calhoun from Class A Myrtle Beach to Rookie League Chicago N (ACL). |
| Demoted RF Carter Trice from Triple A Iowa to Double A Tennessee. |
| Demoted LF Spencer Horwitz from Triple A Iowa to Double A Tennessee. |
| Demoted 1B Drew Bowser from Triple A Iowa to Double A Tennessee. |
| Promoted C Wally Soto from High-A South Bend to Double A Tennessee. |
| Promoted C Adriel Calderon from High-A South Bend to Double A Tennessee. |
| Promoted SS Josh Rivera from High-A South Bend to Double A Tennessee. |
| Promoted LF Isaiah Greene from High-A South Bend to Double A Tennessee. |
| Demoted LF Adam Duvall from Triple A Iowa to Double A Tennessee. |
| Demoted LF Eloy Jimenez from Triple A Iowa to Double A Tennessee. |
| Sent C Jesus Valero from Class A Myrtle Beach to High-A South Bend. |
| Sent C Michael Carico from Class A Myrtle Beach to High-A South Bend. |
| Sent 3B Cristian Hernandez from Class A Myrtle Beach to High-A South Bend. |
| Sent SS Ivan Arias from Class A Myrtle Beach to High-A South Bend. |
| Sent SS Chris Maldonado from Class A Myrtle Beach to High-A South Bend. |
| Sent CF Caden Sorrell from Class A Myrtle Beach to High-A South Bend. |
| Sent SS Kyle Dernedde from Class A Myrtle Beach to High-A South Bend. |
| Sent SS Elijah Clayton from Class A Myrtle Beach to High-A South Bend. |
| Promoted C Carlos Altuve from Rookie League Chicago N (ACL) to Class A Myrtle Beach. |
| Promoted 3B Leighton Banjoff from Rookie League Chicago N (ACL) to Class A Myrtle Beach. |
| Promoted SS Christopher Paciolla from Rookie League Chicago N (ACL) to Class A Myrtle Beach. |
| Promoted 1B Dale Francis from Rookie League Chicago N (DSL) to Class A Myrtle Beach. |
| Promoted SS Rob Gordon from Rookie League Chicago N (DSL) to Class A Myrtle Beach. |
| Promoted SS Jake Kendro from Rookie League Chicago N (DSL) to Class A Myrtle Beach. |
| Promoted CF Bristol Carter from Rookie League Chicago N (DSL) to Class A Myrtle Beach. |
| Promoted 2B Nick Allen from Rookie League Chicago N (DSL) to Class A Myrtle Beach. |
| Promoted SS Jack Goodman from Rookie League Chicago N (DSL) to Class A Myrtle Beach. |
| Promoted RF Ethan De Cuba from Rookie League Chicago N (DSL) to Class A Myrtle Beach. |
| Thursday, March 25th , 2027 |
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| Signed international amateur SP Arturo Donado out of Dominican Republic to a minor league contract. |
| Thursday, March 18th , 2027 |
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| Signed international amateur SP Jorge Ventura out of Venezuela to a minor league contract. |
| Thursday, March 11th , 2027 |
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| Signed international amateur LF Arturo Egoavil out of Dominican Republic to a minor league contract. |
| Sunday, March 7th , 2027 |
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| Signed international amateur CF Juan Jaimes out of Dominican Republic to a minor league contract. |
| Wednesday, March 3rd , 2027 |
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| Signed international amateur C Gilberto Terrazas out of Venezuela to a minor league contract. |
| Monday, March 1st , 2027 |
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| Promoted RP Tayron Guerrero from Rookie League Chicago N (DSL) to Triple A Iowa. |
| Promoted RP Alfredo Romero from Rookie League Chicago N (DSL) to Triple A Iowa. |
| Promoted SP Clayton Beeter from Rookie League Chicago N (DSL) to Triple A Iowa. |
| Promoted SP Brayan Bello from Rookie League Chicago N (DSL) to Triple A Iowa. |
| Promoted SP Kutter Crawford from Rookie League Chicago N (DSL) to Triple A Iowa. |
| Promoted SP Luis De La Rosa from Rookie League Chicago N (DSL) to Triple A Iowa. |
| Promoted SP Juan Daniel Encarnacion from Rookie League Chicago N (DSL) to Triple A Iowa. |
| Promoted SP Nate Fisher from Rookie League Chicago N (DSL) to Triple A Iowa. |
| Promoted CL Jorge Garcia from Rookie League Chicago N (DSL) to Triple A Iowa. |
| Promoted SP Tony Gonsolin from Rookie League Chicago N (DSL) to Triple A Iowa. |
| Promoted RP Anthony Gose from Rookie League Chicago N (DSL) to Triple A Iowa. |
| Promoted SP Josiah Gray from Rookie League Chicago N (DSL) to Triple A Iowa. |
| Promoted SP Ben Gross from Rookie League Chicago N (DSL) to Triple A Iowa. |
| Promoted SP Thomas Hatch from Rookie League Chicago N (DSL) to Triple A Iowa. |
| Promoted LF Spencer Horwitz from Rookie League Chicago N (DSL) to Triple A Iowa. |
| Promoted SP Tanner Houck from Rookie League Chicago N (DSL) to Triple A Iowa. |
| Promoted SP Adrian Houser from Rookie League Chicago N (DSL) to Triple A Iowa. |
| Promoted RP Carlos Jimenez from Rookie League Chicago N (DSL) to Triple A Iowa. |
| Promoted SP Dean Kremer from Rookie League Chicago N (DSL) to Triple A Iowa. |
| Promoted RP Yenrri Rojas from Rookie League Chicago N (DSL) to Triple A Iowa. |
| Sunday, February 28th , 2027 |
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| Signed international amateur SP Frank Bautista out of Dominican Republic to a minor league contract. |
| Wednesday, February 24th , 2027 |
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| LF Ezequiel Pagan was claimed off waivers by Las Vegas. |
| Monday, February 22nd , 2027 |
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| Assigned LF Cole Roederer to Triple A Iowa. |
| Friday, February 19th , 2027 |
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| Recalled CF Kevin Alcantara from Double A Tennessee. |
| Recalled SS Geuri Lubo from Double A Tennessee. |
| Recalled RP Daniel Palencia from Triple A Iowa. |
| Recalled 3B James Triantos from Triple A Iowa. |
| Recalled 1B Drew Bowser from High-A South Bend. |
| Recalled 2B Matt Shaw from Triple A Iowa. |
| Recalled 3B Reginald Preciado from Triple A Iowa. |
| Recalled SP Nathan Dettmer from Triple A Iowa. |
| Recalled RP Luke Little from Triple A Iowa. |
| Recalled SP Ofelky Peralta from Triple A Iowa. |
| Recalled RF Carter Trice from High-A South Bend. |
| Recalled SP Richard Gallardo from Triple A Iowa. |
| Recalled SP Porter Hodge from Triple A Iowa. |
| Invited non-roster C Moises Ballesteros to Spring Training camp. |
| Invited non-roster C Victor Caratini to Spring Training camp. |
| Invited non-roster LF Eloy Jimenez to Spring Training camp. |
| Invited non-roster LF Jon Berti to Spring Training camp. |
| Invited non-roster RP Michael Arias to Spring Training camp. |
| Invited non-roster 1B Bryce Ball to Spring Training camp. |
| Invited non-roster C Moises Ballesteros to Spring Training camp. |
| Invited non-roster C Victor Caratini to Spring Training camp. |
| Invited non-roster LF Eloy Jimenez to Spring Training camp. |
| Invited non-roster LF Jon Berti to Spring Training camp. |
| Invited non-roster RP Michael Arias to Spring Training camp. |
| Invited non-roster 1B Bryce Ball to Spring Training camp. |
| Promoted LF Adam Duvall from Rookie League Chicago N (DSL) to Triple A Iowa. |
| Wednesday, February 10th , 2027 |
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| LF Ezequiel Pagan was designated for assignment and placed on waivers. |
| Placed SS Willy Adames on the active roster. |
| LF Ezequiel Pagan was designated for assignment and placed on waivers. |
| Placed SS Willy Adames on the secondary (40-man) roster. |
| Placed SS Willy Adames on the active roster. |
| Friday, February 5th , 2027 |
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| Signed free agent LF Jon Berti to a minor league contract. |
| Signed free agent C Victor Caratini to a minor league contract with a major league option. |
| Signed free agent SS Willy Adames to a 1-year contract worth a total of $2,600,000. |
| Signed free agent LF Eloy Jimenez to a minor league contract. |
| Monday, February 1st , 2027 |
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| Signed free agent SP Dean Kremer to a minor league contract. |
| Signed free agent SP Tanner Houck to a minor league contract. |
| Signed free agent RP Anthony Gose to a minor league contract. |
| Signed free agent SP Walker Buehler to a 4-year contract worth a total of $360,000,000. |
| Signed free agent SP Josiah Gray to a minor league contract. |
| Signed free agent SP Thomas Hatch to a minor league contract. |
| Signed free agent SP Adrian Houser to a minor league contract. |
| Signed free agent RP Tayron Guerrero to a minor league contract. |
| Signed free agent SP Jonathan Loáisiga to a 2-year contract worth a total of $66,400,000. |
| Signed free agent SP Ben Gross to a minor league contract. |
| Signed free agent LF Spencer Horwitz to a minor league contract. |
| Signed free agent RP Carlos Jimenez to a minor league contract. |
| Placed SP Jonathan Loáisiga on the active roster. |
| LF Cole Roederer was designated for assignment and placed on waivers. |
| Placed SP Walker Buehler on the active roster. |
| Purchased the contract of RP Andres Diaz from Triple A Iowa. |
| Placed SP Jonathan Loáisiga on the secondary (40-man) roster. |
| Placed SP Jonathan Loáisiga on the active roster. |
| LF Cole Roederer was designated for assignment and placed on waivers. |
| Placed SP Walker Buehler on the secondary (40-man) roster. |
| Placed SP Walker Buehler on the active roster. |
| Purchased the contract of RP Andres Diaz from Triple A Iowa. |
| Saturday, January 30th , 2027 |
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| Signed international amateur 2B Juan Garza out of Dominican Republic to a minor league contract with a $5,500,000 signing bonus. |
| Monday, January 25th , 2027 |
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| Promoted international complex member SP Julio Baca to Rookie League Chicago N (DSL). |
| Promoted international complex member LF Alfredo Buzo to Rookie League Chicago N (DSL). |
| Promoted international complex member SP Daniel Ciccoritti to Rookie League Chicago N (DSL). |
| Promoted international complex member LF Kai Ammerbach to Rookie League Chicago N (DSL). |
| Promoted international complex member SP Wilfredo Carrillo to Rookie League Chicago N (DSL). |
| Promoted international complex member SP Sergio Jiron to Rookie League Chicago N (DSL). |
| Promoted international complex member SS David Conejo to Rookie League Chicago N (DSL). |
| Promoted international complex member SP Juan Fuentes to Rookie League Chicago N (DSL). |
| Promoted international complex member SP Juan Estrello to Rookie League Chicago N (DSL). |
| Promoted international complex member RF Bruce Jeffes to Rookie League Chicago N (DSL). |
| Promoted international complex member 3B Juan Leanos to Rookie League Chicago N (DSL). |
| Promoted international complex member SP Ciro Lepore to Rookie League Chicago N (DSL). |
| Promoted international complex member SP Ernesto Lovera to Rookie League Chicago N (DSL). |
| Promoted international complex member SP Gregorio Navarro to Rookie League Chicago N (DSL). |
| Promoted international complex member SP Juan Rivas to Rookie League Chicago N (DSL). |
| Promoted international complex member CF Quintin Woollett to Rookie League Chicago N (DSL). |
| Promoted international complex member SP Ismael Villeda to Rookie League Chicago N (DSL). |
| Promoted international complex member 3B Vicente Velasco to Rookie League Chicago N (DSL). |
| Promoted international complex member 1B Onorato Scalia to Rookie League Chicago N (DSL). |
| Monday, January 18th , 2027 |
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| Placed 1B Nathaniel Lowe on the active roster. |
| Placed 1B Nathaniel Lowe on the secondary (40-man) roster. |
| Placed 1B Nathaniel Lowe on the active roster. |
| Thursday, January 14th , 2027 |
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| Signed free agent 1B Nathaniel Lowe to a 3-year contract worth a total of $112,800,000. |
| Friday, January 8th , 2027 |
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| Signed free agent CL Jorge Garcia to a minor league contract. |
| Friday, January 1st , 2027 |
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| Signed free agent SP Kutter Crawford to a minor league contract. |
