Per Article XIX-A of the CBA, any player on an MLB 40-man roster who has accrued at least five years of MLB Service Time (as well as an international player with Article XIX-A contractual rights) has the right to refuse an Outright Assignment to the minors, or the player can elect to be a free-agent immediately upon being outrighted, or he can accept the Outright Assignment and defer his option to elect free-agency until after the conclusion of the MLB regular season.

However, an Article XIX-A player who accepts an Outright Assignment and defers his option to elect free-agency until after the conclusion of the MLB regular season forfeits his right to elect free-agency (as an Article XIX-A minor league free-agent) if he is added back to an MLB 40-man roster prior to the conclusion of the MLB regular season.

If a player with Article XIX-A rights refuses an Outright Assignment but does not elect free-agency, the club must either retain the player on the club's MLB Reserve List (40-man roster), trade the player, or give the player his unconditional release.

If a player with Article XIX-A rights does not refuse an Outright Assignment but then elects to be a free-agent immediately after being outrighted, his contract is terminated and he receives no termination pay. But if the player accepts the Outright Assignment and defers his right to be a free-agent until the conclusion of the MLB regular season, the player continues to get paid, receiving the balance of his salary through to the end of the season. And then if the outrighted player is not subsequently added back to an MLB 40-man roster prior to the conclusion of the MLB regular season, the player can elect free-agency anytime beginning on the day after the conclusion of the MLB regular season through October 15th.

A player with Article XIX-A rights can waive his right (in advance) to refuse an outright assignment or elect free-agency if outrighted, but the waiver cannot be signed more than ten days prior to MLB Opening Day, the player has the right to designate in advance which minor league team to which he can be assigned, and the waiver automatically expires if the player is not outrighted to the minors within 45 days or by the 45th day of the MLB regular season (whichever is later).

CUBS ARTICLE XIX-A PLAYERS (last updated 11-4-2023):
Yan Gomes, C
Ian Happ, OF 
Kyle Hendricks, RHP
Drew Smyly, LHP 
Seiya Suzuki, OF (International player with Article XIX-A rights) 
Dansby Swanson, INF 
Jameson Taillon, RHP 

Per Article XX-D of the CBA, a player on an MLB 40-man roster who has been outrighted previously in his career and/or who has accrued at least three years of MLB Service Time can elect to be a free-agent if he is sent outright to the minors. (An international player with Article XX-D contractual rights also has the right to elect free-agency if outrighted). The outrighted Article XX-D player can elect to be a free-agent immediately upon being outrighted, or he can accept the Outright Assignment and defer his option to elect free-agency until after the conclusion of the MLB regular season. However, a player eligible to be a free-agent if outrighted who accepts an Outright Assignment and defers his option to elect free-agency until after the conclusion of the MLB regular season forfeits his right to elect free-agency (as an Article XX-D minor league free-agent) if he is added back to an MLB 40-man roster prior to the conclusion of the MLB regular season.

CUBS ARTICLE XX-D PLAYERS (updated 11-17-2023):
Adbert Alzolay, RHP 
Nico Hoerner, INF 
Mark Leiter Jr, RHP
Nick Madrigal, INF 
Julian Merryweather, RHP 
Michael Rucker, RHP 
Mike Tauchman, OF
Patrick Wisdom, INF-OF

If a player eligible to be a free-agent if outrighted elects to be a free-agent immediately, his contract is terminated and he receives no termination pay. But if the Article XX-D player accepts the Outright Assignment and defers his right to be a free-agent until the conclusion of the MLB regular season, the player continues to get paid, receiving the balance of his salary through to the end of the season. And then if the outrighted Article XX-D player is not subsequently added back to an MLB 40-man roster prior to the conclusion of the MLB regular season, the player can elect free-agency anytime beginning on the day after the conclusion of the MLB regular season through October 15th.

A player who has not previously been outrighted to the minors or who has not yet accrued three years of MLB Service Time but who qualified as a "Super Two" player after the conclusion of the previous MLB regular season can elect free-agency if he is outrighted to the minors, but an outrighted "Super Two" player cannot defer free-agency until the conclusion of the MLB regular season. To become a free-agent, the outrighted "Super Two" player must elect free-agency immediately.

CUBS ARTICLE XX-D "SUPER TWO" PLAYERS (updated 10-2-2023):
Justin Steele, LHP  

Once an outrighted player eligible to elect free-agency becomes a free-agent, the player can sign a major league or minor league contract with any club, including the player's previous club.

The club must advise an Article XIX-A or Article XX-D player in writing when it has decided to outright the player to the minors. (The club can notify the player up to eight days in advance of the assignment during the off-season or if the player is out of minor league options, and up to four days in advance if the assignment is contemplated during Spring Training or during the MLB regular season). Once notified, the player must make his decision whether to accept or decline the assignment within three days if he is outrighted during the off-season, or within two days if he is outrighted during Spring Training or during the MLB regular season.

1. A player cannot be sent outright to the minors beginning at 5 PM (Eastern) on the third day prior to the Rule 5 Draft through the conclusion of the draft.

2. A Rule 5 "Selected Player" cannot be outrighted to the minors until restrictions have been removed, and then no earlier than 20 days prior to the start of the MLB regular season.

MLB RULE 5 SELECTED PLAYERS ON CUBS MLB RESERVE LIST (updated 3-12-2021): 
NONE AT THIS TIME

3. A Rule 5 "Draft-Excluded Player" can be outrighted to the minors only if Outright Assignment Waivers are requested no later than 2 PM (Eastern) on the 5th day after the final game of the World Series, and if a "Draft-Excluded Player" is not outrighted to the minors prior to the Rule 5 Draft, the player cannot be sent to the minors any earlier than 20 days prior to the start of the MLB regular season (same as a Rule 5 player).

MLB RULE 5 DRAFT-EXCLUDED PLAYERS ON CUBS MLB RESERVE LIST (updated 11-14-2023): 
Michael Arias, RHP (see NOTE)
Porter Hodge, RHP (see NOTE)
Bailey Horn, LHP (see NOTE)
Luke Little, LHP   
Luis Vazquez, INF (see NOTE)
NOTE: Once Draft-Excluded Player status is removed, player can be sent outright to minors even if he is injured up until 15th day prior to start of 2024 MLB regular season. 

4. An unsigned player who is not eligible to be an Article XIX-A or Article XX-D minor league free-agent if outrighted but who would have been an MLB Rule 9 minor league free-agent (either a Six-Year FA or Second-Contract FA) if the player had been on a minor league reserve list cannot be outrighted to the minors after 5 PM (Eastern) on the 5th day after the final game of the World Series (or 5 PM Eastern on October 15th if the World Series is canceled) unless and until either the player signs a Major League contract for the following season, has his previous season's contract unilaterally and automatically renewed by the club on March 1st, or agrees (in advance) to sign a minor league contract for the following season (if the Outright Assignment is contemplated prior to a Major League contract being tendered).

POST-2023 UNSIGNED MLB RULE 9-ELIGIBLE PLAYERS ON CUBS MLB RESERVE LIST (updated 10-2-2023): 
Miguel Amaya, C 
Javier Assad, RHP 
Alexander Canario, OF
Jose Cuas, RHP 
Miles Mastrobuoni, INF 
Christopher Morel, INF-OF  
Keegan Thompson, RHP 

5. If a player accrues at least one day of MLB Service Time in a season and then is outrighted to the minors prior to being tendered a Major League contract for the following season, the player's minor league monthly salary for the following season must be at least 80% of his final monthly salary from the previous season.

1. An injured player cannot be outrighted to the minors during the MLB regular season. 

2. Most injured players can be outrighted to the minors during a period of time beginning on the day after the conclusion of the MLB regular season up until reserve lists are filed in November, but an injured "Rule 5 Player" can be outrighted during this period only after Rule 5 restrictions have been removed, and an injured "Draft-Excluded Player" can be outrighted during this period only if Outright Assignment Waivers are requested by 2 PM (Eastern) on the 4th day after the final game of the World Series.  

3. An injured player who has accrued less than three years of MLB Service Time in his career and who did not accrue any MLB Service Time the previous season, has not previously been outrighted to the minors, and who was not selected in the immediately-preceding Rule 5 Draft, can be outrighted to the minors during a period of time beginning on the day after the conclusion of the MLB regular season up until the 15th day prior to the start of the next MLB regular season. 

CAN BE OUTRIGHTED IF INJURED UNTIL 15TH DAY PRIOR TO 2024 MLB OPENING DAY (last updated 10-2-2023):
Kevin Alcantara, OF
Ben Brown, RHP 
Brennen Davis, OF

4. An injured MLB Rule 9-eligible player who otherwise would qualify to be outrighted during the off-season and Spring Training can be outrighted only after he has either signed a Major League contract for the upcoming season or had his previous season's contract renewed by the club, or agrees (in advance) to sign a minor league contract for the upcoming season (if the Outright Assignment is contemplated prior to a Major League contract being tendered).

MLB RULE 9-ELIGIBLE PLAYER - CAN BE OUTRIGHTED IF INJURED ONLY IF CONTRACT RESTRICTIONS MET (last updated 10-2-2023):
NONE AT THIS TIME  

5. An injured player with Draft Excluded Status who otherwise would qualify to be outrighted during the off-season and Spring Training can be outrighted only during a five-day window starting on the 20th day prior to the start of the MLB regular season up until the 15th day prior to the start of the MLB regular season.

DRAFT-EXCLUDED PLAYER - CAN BE OUTRIGHTED IF INJURED ONLY DURING FIVE-DAY WINDOW IN MARCH (last updated 11-14-2023):
Michael Arias, RHP 
Porter Hodge, RHP 
Bailey Horn, LHP 
Luis Vazquez, INF