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Number 19- Charlie Blackmon
Not much competition for number 19 and Charlie Blackmon will likely keep adding on to his resume in the next few seasons.
In parts of nine seasons with the Rockies, he has hit .304/.360/.509 with an OPS+ of 116. Since he has been an everyday player (six seasons), those numbers are even better as he has hit .306/.365/.520 with an OPS+ of 120. He has been an All-Star four times, won two Silver Slugger Awards, and ranked in NL MVP voting twice which includes his fifth-place finish in 2017.
Number 20- Chris Iannetta
This another one that doesn’t have much competition.
Chris Iannetta wore #20 for his first tenure with the Rockies (2006-2011). In those six seasons, he played in 458 games and he hit .235/.357/.430 with an OPS+ of 99 and accumulated a bWAR of 8.1. When he returned in 2018, he wore #22 since Ian Desmond has worn the number 20 since he joined the Rockies.
Only Bill Swift, Todd Greene, Wilin Rosario, and the aforementioned Desmond have worn the number 20 for multiple seasons in a Rockies uniform and none were as good (or played as long) with the Rockies as long as Iannetta did in his first tenure with the Rockies.