
‘Tis the season for tough decisions for MLB front offices. The Cleveland Guardians had to make a few decisions on Tuesday about which prospects to add to the 40-man roster for the 2026 season.
In the aftermath, Cleveland added INF Angel Genao, OF Kahlil Watson, RHP Austin Peterson, and RHP Yorman Gomez to the 40-man roster, but had to designate Nic Enright to make room for an additional prospect.
The decision to DFA Enright, who has gone through a long, difficult journey to MLB, was one tough choice.
Another one was the choice not to add prospect Milan Tolentino to the 40-man roster. Since Tolention was signed five years ago in 2020, he hasn’t made his big-league debut yet, and isn’t on the roster; he’s therefore eligible to be selected in the Rule 5 Draft by an opposing team.
The decision not to protect Tolentio could be one that the Guardians come back to regret.
Tolentino is coming off an intriguing minor league season. He didn’t necessarily hit for power, but the left-handed hitter did start to hit for some power. Tolentino slashed .216/.314/.437, with an OPS of .751, including 20 home runs and 20 doubles.

Cleveland has had a difficult time developing power-hitters over the past few years, and it looked like they were on the right track with Tolentino. Now, they could risk losing him for nothing.
In order for a player selected in the Rule 5 Draft to remain with another MLB team, they must be on the team’s active 26-man roster. That’s why young players at lower levels of the minor leagues typically aren’t selected, even if they do have some potential.
That’s not the case with Tolentino, though. He’s 24 years old and has already reached Triple-A, and continues to trend in the right direction.
A team in need of some more offense, and confident they could help him consistently swing his bat for power, could be willing to take the chance on Tolineto and see what he can do against big-league pitching during spring training, similar to what the Guardians did in 2024 with Deyvison De Los Santos.
It’ll be interesting to see what happens to Tolentino during the Rule 5 Draft, and if he is selected, what his career ends up being like away from the Guardians.