There's some mighty-vintage button copy on the original section of CA 85, probably 50+ years old. This one in particular has always bugged me:
https://flic.kr/p/287i53w
The sign says CA 237 and southbound US 101 are at the next exit, but it really should be TO South 101, since it's another 3 miles until you actually reach 101 that way. It seems surprising that the sign has been wrong for decades.
(And a closer 85 north -> 101 south connection exists at Moffett Blvd. anyway, although that wouldn't be the best route to the control city of San Jose.)
As this sign is located in my neck of the woods, let me try to shed some light on why US 101 appears on the CA-237 exit signs.
Originally, at the CA-237 exit the gantry held 3 signs... CA-237/US 101 South to Oakland/San Jose, a 1/2 mile advance guide sign for Evelyn Avenue and a pull-through showing US 101 North to San Francisco. Here's a photo of the old signs from the AARoads Gallery...

To me, this a major decision point for travelers on northbound 85. Because there is no direct ramp from north 85 to south 101, these signs are directing drivers bound for south 101 to use 237 and those bound for north 101 to stay on 85.
Unfortunately, when this gantry was replaced back in the early 2000's with a new gantry, the signs were relocated to before the gore point...

So the new gantry held signs for the CA-237 exit and the Evelyn Ave advance guide sign but because it didn't span the entire freeway like the old one did, the pull-through was put on a separate gantry located *after* the 237 exit, seen in the background of the above photo. It's most definitely an odd setup and a case where the shields used on the old signs made sense (to me anyways). Note: the US 101 North pull-through has since been replaced with a 1 1/2 mile advance guide sign for northbound 101 (
GMSV).
IINM, there was a discussion about this particular Caltrans signing practice in another thread and how that is slowly starting to change. For example, the north Mathilda Ave exit from north 101 used to read "Mathilda Avenue North/CA-237 EAST" but was changed to "TO EAST CA-237/Mathilda Ave North" as part of a recent sign replacement project.