Final 2 names for Baby Boy

This is my first time posting but I spend a lot of time on the site.

My husband and I are expecting our first child in [name]May[/name]. We have narrowed the field of names to 2 for each gender (I have posted the girls’ finalists in the other forum). I am seeking your input.

First names:
[name]Calvin[/name] - has some meaning for my husband who spent some time mentoring at-risk youth and had a special connection to a boy named [name]Calvin[/name]
[name]Winston[/name] - we both have history degrees and love the [name]Churchill[/name] connection here

Middle name (must start with J; Jewish tradition to honor my husband’s recently deceased grandfather). We are open to new ideas on middles:

[name]Jude[/name], [name]Judah[/name], [name]Jacob[/name]

What do you think?

I love [name]Calvin[/name] and think it sounds wonderful paired with [name]Judah[/name].

I like [name]Winston[/name] [name]Jude[/name]!

I like [name]Calvin[/name] Jacobus.
I was considering [name]Jacob[/name] but found the flow difficult with [name]Calvin[/name] and though this Dutch/Late [name]Roman[/name] variant would be a great alternative.

second choice: [name]Winston[/name] [name]Judah[/name]
[name]Winston[/name] is a second choice because it just doesn’t feel as fresh and unique as [name]Calvin[/name]. To me it just fits into the [name]Ashton[/name], [name]Peyton[/name] thing despite it’s [name]Churchill[/name]-y-ness.

I originally said I didn’t want any boys’ names that were two syllables ending in N. I feared the [name]Aiden[/name]/[name]Logan[/name]/[name]Ethan[/name]/[name]Ashton[/name]/[name]Peyton[/name] thing that lexiem mentioned. Ironically, we ended up narrowing down to 2 that fit that description. Good to know that [name]Calvin[/name] feels less like that to you than [name]Winston[/name], thanks!

I really like but [name]Calvin[/name] and [name]Winston[/name] but I think [name]Winston[/name] is a little bit pretentious. [name]Calvin[/name] [name]Jude[/name] is lovely.

I have a 10 yr old named [name_m]Calvin[/name_m] (after [name_m]John[/name_m] [name_m]Calvin[/name_m]). We [name_f]LOVE[/name_f] the name. Our other son is [name_m]Lincoln[/name_m]. We’re expecting again and are considering the name [name_m]Churchill[/name_m].
[name_m]Calvin[/name_m] [name_m]Jeremiah[/name_m]
[name_m]Calvin[/name_m] [name_u]Jude[/name_u]

Have fun!

[name_m]Winston[/name_m] [name_u]Jude[/name_u] sounds pretty badass, but I don’t like that it’s a brand of cigarettes, and I prefer that [name_m]Calvin[/name_m] has the nn option of [name_u]Cal[/name_u].

[name_m]Calvin[/name_m] [name_u]Jude[/name_u] sounds awesome as well. I also like [name_m]Jonah[/name_m] for a J name.