I would like to start off by saying that I'm not expert of radio propagation, so my response isn't the law of what could happen.
That being said, I'm not sure it's possible with Colorado's terrain. From what I can tell by looking at area topographic maps, believe that Douglas and El Paso counties regions are several thousand feet higher than Denver and Pueblo. Some numbers are Denver being 5,280 ft, Pueblo being 4,692 ft, and Monument being 6,975 ft right in between the two. My thoughts and very rough estimations is that you would need a pole the height of your elevation to be line-of-sight with Denver.
Denver does operate some stuff off Mt. Morrison (7,881 ft) west of the city including P25 and City Services EDACS (which I've heard some public safety stuff might be found on), however farther west means more terrain. The line of sight to that location would probably mean going through places like the Westcreek area (7,484 ft), and we haven't even accounted for the decrease in elevation once you reach the Pueblo area. This would probably also need a pole several thousand feet high to obtain line-of-sight with that site.
We then add 100 miles of propagation loss, which might be hard enough to overcome with perfect conditions, and I don't think that one can hear Denver via practical means from Pueblo.
