A Minor Point
The following Cubs have used up their last minor league option year in 2019 and thus will be out of options come Spring Training 2020 (presuming they are still on the Cubs 40-man roster):
Carl Edwards Jr
Alec Mills
Randy Rosario
Duane Underwood Jr
Mark Zagunis
Mike Montgomery and Allen Webster (as well as Article XIX-A players Brad Brach, Xavier Cedeno, and Tyler Chatwood) were already out of minor league options coming into the 2019 season, and although he is not yet on the Cubs 40-man roster, Danny Hultzen is also out of minor league options (which matters only if he were to be added to the Cubs 40-man roster at some point in the future).
Kyle Ryan came into 2019 with one minor league option year remaining, and although he was optioned to AAA Iowa at the end of Spring Training, he spent only nine days on Optional Assignment, so as long as he spends no more than ten more days on Optional Assignment to the minors over the balance of the 2019 season, he will still have one minor league option remaining in 2020. (If a player spends less than 20 days on Optional Assignment to the minors in a given season, an option year is not spent).
Ideally, what a club would want to do with a player the club wants to keep but who is out of options is non-tender the player on 12/2, and then sign him to a minor league contract (for MLB 40-man roster money or maybe even a little bit more and with an NRI to Spring Training) after the Rule 5 Draft. That way the player basically gets what he would have received if he had been on the 40 at the start of Spring Training, but the club is able to remove the player from the 40-man roster without exposing the player to waivers and without taking the risk that he might be selected in the Rule 5 Draft, and then the club can send the player to the minors out of Spring Training (because he is already signed to a minor league contract and thus Outright Assignment Waivers would not need to be secured). This is what the Cubs did with Allen Webster post-2018, Taylor Davis post-2017, Zac Rosscup, Conor Mullee, and Gerardo Concepcion post-2016, and Jack Leathersich post-2015.
However, there are essentially two problems with this approach.
The first is that the player has to agree to the proposition. He can't be forced to do it. It's his choice. That's why a club usually has to offer the player at least the same money (maybe even a bit more money) than he would have gotten had he remained on the 40.
And secondly, the player's slot on the MLB 40-man roster might be needed for another player before contracts are tendered (or not tendered) on December 2nd. (Off-season minor league reserve lists -- the ones that are used to determine who can and cannot be selected in the Rule 5 Draft -- must be finalized and submitted to the MLB Commissioner by November 20th, almost two weeks prior to the date contracts are tendered or not tendered). Sometimes a club just can't wait for a player to be non-tendered.
One other point is that just because a player on an MLB 40-man roster is out of minor league options doesn't mean the player has no value going into Spring Training or during the course of the season. It just means his value is diminished (somewhat) because he cannot be sent back & forth to AAA during the course of the season (on the so-called "Chicago - Des Moines Shuttle") as easily as a player who has minor league options available. Outright Assignment Waivers (which are irrevocable) would have to be secured in order to send a player who is out of options to the minors, and there is always a chance that a player the club wants to keep could get claimed off waivers by another club, or, in the case of a player with Article XX-D rights (player has been outrighted previously in his careeer, has accrued at least three years of MLB Service Time, or qualified as a "Super Two" player after the previous season), he can elect free-agency after being outrighted.
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