Depending on the ride I may carry more tools, but by "normal" minimal set (and what I'm carrying today, in a Carradice Barley on the back of
Red) is:
Mini-pump
Three CO
2 cartridges.
CO
2 inflator
Two inner tubes
Topeak
Alien II mult-tool (26 tools in 1 !)
5" adjustable spanner
Leatherman
Skeletool CXKevlar spokePark Boot
Two
Michelin tyre leversA VAR tool
A small
Tip-Top repair kitA couple of toestraps
A random selection of cable ties
A 6mm, 5mm, 4mm and 3mm ball ended Allen keys (the 6mm and 3mm are unusual for me, but I just fitted the Bagman with them)
A spokey
A small set of nuts, bolts and washers (mostly M5, but normally also a set of old SPD bolts)
When out with others (and carrying a pannier) I have also carried more inner tubes of various sizes, a complete set of Allen keys (1.5mm to 10mm iirc), proper straight and crosshead screwdrivers, a large adjustable spanner, a spare tyre.
I often carry "proper" 5mm and 4mm ball ended Allen keys, because whilst there are such sizes on the multi-tool, often it's much easier to use the proper tools, and 4mm and 5mm cover the vast majority of cases (the multi-tool can be difficult to get into certain locations because of it's relative bulk).
I've used most of those tools (although not all of the bits of the Alien II), although probably more on other people bikes than my own!
I've never in my life broken a chain! I understand it does happen sometimes to fixie riders, but unless you're doing a tour of chain-wearing length, I can't see the need.
Spokey - you mean one of those lightweight plastic ones? ...
I've broken a couple of chains, and needed the tool to remove damaged links and remake the chain. Even with a quick-link of some species, I would have need the tool to remove the bent and borked links.
Several times I've used Spokeys to tweaks spokes to compensate for a broken spokes, or just on a badly maintained bike!
I've found rubber gloves to be a nuisance when trying to handle small or fiddly parts, and the easiest solution to black hands, is to make sure that you wear black shorts, so have somewhere inconspicuous to wipe your hands!
I'll also carry a
15mm laser stubby spanner when on one of the single-speed bikes, because that's much easier to use than an adjustable, and doesn't risk rounding off the heads.