For quick reference here's the all-time hitting and pitching leaders for the Cubs. I was in the Santo over Sosa camp until looking that over and realizing how much Sosa was damaged by his non-Cub years. I think I'd give Sosa the edge over Santo now. That said, I'm still not sure he's in the top 5. Brown appears to me to be the best Cub of all time, so of course he was left off. I've always had a soft spot for Gabby Hartnett, so I think I'd put him in over Sosa. Banks's half career at SS is enough for me to put him over Sosa. That leaves Anson, Sosa, Williams, Jenkins, Alexander, and Sandberg for the last 2 spots. (Chance gets some bonus points for the world series, but not enough to overcome his small # of ABs, and his not up to snuff #s.) Williams and Sosa are real close on offensive #s, Sosa has the slight edge in OPS+, but his is SLG heavy, so that pretty much makes up the difference. Williams's extra ABs gives him the slight edge. To the best of my knowledge, I don't believe Williams was any worse than Sosa in the field. Anson's OBP is pretty sick when compared to the league OBP, yet somehow I was still underwhelmed. I'm inclined to give Sosa the slight edge against him. Additionally, I discounted guys like Clarkson and Pfeister for pitching in the 1800s where they only played about 5 seasons for the Cubs, so it seems unfair to include Anson's time from the same era. Jenkins amassed a lot of time elsewhere, but is still the all time leader in GS for the Cubs and is 3rd all time in Innings. That said, looking back over his #s, he doesn't belong anywhere in a top 5 discussion, and probably isn't even a top 10 Cub. Alexander didn't have a lot of seasons with the Cubs, but when he was around, he was pretty phenomenal. I put him a notch above Vaughn for Cubs pitchers and probably a notch below Sosa if just because he didn't have the longevity as a Cub that Sosa did. Which leaves Sandberg, which is difficult for me to look at objectively, as he's my favorite player of all time. Sandberg's got a ~1500 AB edge in longevity and a huge edge in defense. Sosa has the slight edge in OBP and a huge edge in SLG. Both were good base stealers in their younger years, but lost some speed as they got older. Sandberg remained a good baserunner, while Sammy was likely down to below average towards the end. Ryno had the fundamentals, but Sosa's #s are just too much to ignore, even with Sandberg's great defense. I grudingly give it to Sosa. My rough sketch of a top 10: Brown Hartnett Banks Williams Sosa Santo Sandberg Anson Alexander Hack? I'm not sure on Hack, I'd have to take a long look at a lot of other guys, but on a quick skim, he's who I'd put there, with maybe Vaughn challenging him for the spot.