Hmmm. I agree with you that the sound is very masculine. There’s the president [name]James[/name] [name]Madison[/name], and the family history for you. It’s also a place name, which is theoretically neutral.
And yet…your cousin in his twenties naming his daughter [name]Madison[/name] doesn’t quite speak to the comfort of sharing the name with mainly girls. In his generation, there weren’t lots of girl Madisons. I think it’s probably telling that they gave it to a daughter and didn’t hold onto it for a son. It’s not only gone to girls, it’s gone to girls and is VERY popular. It is number 8.
A guy named [name]Chelsea[/name] used to post on here about his experience (his parents picked the name as a place name, in the UK, right before it blew up for girls in the US - then they later moved to the US). He has a blog entry on the blogs here if you can find it. He generally cautioned strongly against this sort of thing and didn’t have a completely positive experience (but it wasn’t completely negative).
I think one challenge is that there’s no masculine nickname to it. [name]Maddie[/name] is very girly too with [name]Madeline[/name]. I suppose he could try to pull off [name]Matt[/name].
The etymology of [name]Madison[/name], I have seen, is [name]Matthew[/name]'s son or [name]Matthias[/name]'s son. I’ve also read [name]Maud[/name]'s son. Could you consider [name]Matthew[/name] or [name]Matthias[/name]?
I don’t know any guy Madisons…the guy [name]Chelsea[/name] is the closest. I also knew a guy Meriwether. He went by his middle name, I forget what it was, but it was a classically male name, most of his life. In middle age he switched over, I think getting more comfortable, or maybe it was college, I don’t know, but basically as an adult he was fine with it and even with the nickname [name]Meri[/name] which sounded just like [name]Mary[/name]. But yeah, as an adolescent, with all of the identity problems it brings anyway, he wanted the safety of something clear. And [name]Chelsea[/name] would talk about the same process, sort of, although I don’t think he ever tried to go by another name.
SO…ultimately I think it’s much better to put it in the middle (where it is for you), or, if you truly truly feel like you want to put it in front, use something very traditionally masculine in the middle and be prepared for the possibility that he will want to use it. [name]Madison[/name] [name]David[/name], [name]Madison[/name] [name]John[/name], etc.
[name]One[/name] further thought: how far are you from having kids? I can imagine a backlash against the name [name]Madison[/name] for girls…it might fall sharply ([name]Madeline[/name] and [name]Addison[/name] though might still be around…). If that happens, that might make it a little easier on a guy, but I think it’s still going to be a challenge.