I don't even know if I would clean the tools. I dig the patina and dirt myself. That is awesome that they have stayed together like they have.
I am just going to clean off some of the rust that has gotten on some of the sockets there got some moisture in a couple drawers a while back so there is some surface rust
Very very assume would love to see the sets in the boxes.
I have the same box set that belonged to my great grand father but by the time it made it to me no tools left. I would keep it all together and use them just like he did.
Jim
View media item 16833 swivel sockets with one newer replacement
View media item 16837 Dunlap box with ignition tools
View media item 16838 both boxes look a lot alike one Craftsman one Dunlap
View media item 16834small SK socket set with a Plomb ratchet I think this set my Dad put in there when he got it at a Swap meet
View media item 16835Small Craftsman socket set couldn't get a good pic of this
View media item 16836 Mixed socket set Might be another one my Dad put in there
Are the rear corners of that bottom box rounded like the front or squared off?
Cool that your dad let you have them "early" so to speak.
FYI the roller is mid 50's + or - while the top is sixties. I can tell from the logos.
I would guess the back corners on the roller are rounded. (Mine is)
You can also roughly date a lot of the Craftsman tools by a makers mark as sears moved the contracts from tool MFG to tool MFG. (Most of mine are V (Late 60's/early 70's) with some VV which were later)

on the pics of what's in the small metal boxes.
Yes they are rounded I will have to ask My Grandpa next time I see Him when he bought them Hes 87 and still Sharp as a tack and very independent still drives and every thing Hope i get the good aging genes from him
Cool collection. I would give my left nut for anything from either of my grandfathers. Both of whom worked in sawmills in Oregon.
I love the old school OSU avatar.
GO BEAVS
Very nice. I always think of my dad when using the tools he left me. I would restore the bottom cabinet and maybe the top, leave the tools as they are.
Sorry no restore just maybe sand down and paint one spot on the back with some rust so it does not get any worse
My Dad said it got repainted once from my Grandpas coworkers as a surprise when he went on Vacation I guess it was looking a little beat up they thought
What is the odd looking ratchet the last pic? (I'm assuming its a ratchet...) Kind of reverse Micky Mouse ears...
View media item 16842
View media item 16841 Not really sure its some kind of torque wrench with a permanently attached 8 point socket its also set to 10 ft lbs it says My Dad bought it at a swap meet for a buck or two just because it was weird and he left it in here
My father has my grandfather's Kennedy toolbox and my great grandfather's toolbox which is oak with brass hardware. They were both machinists and still full of the original tools. I hope that one day I will end up with them.
One recommendation; resist the urge to reorganize the tools. Keep your granfather's separate from yours so you will always know what was his. It will also keep the vintage toolbox complete with the original tools.
His dad has had the tools for some time so it's probably a safe bet they are not as G'pa had them anyway.
Clean them, clean the boxes, shoot for the apparent organization that you can decipher, but I would not get too **** retentive about preserving the jumble. Interesting that he had cardboard in some drawers as drawer liner. I'd save that as best you can.
Then use them. G'pa would have wanted you to. I"m not saying to thrash then out of existence,but don't be afraid to use them.
(I have a roll top desk in its original finish from the 1880's; one of the first ever manufactured. I still use it. I don't beat it, but museum piece or not, I'm not going to put it under glass...)
My Dad has added some old Craftsman stuff he gotten but didn't really mess with to much in there he has 3 other big roll cabs with a bunch of tools so this was only a sentimental piece
I also plan to use them for some lighter duty work No rusted bolts or cheater bars but its nice to use some of the tools my Grandpa used to make a living for so many years