The Q wording about 'earthbound' isn't too clear if it includes those in orbit, but anyhow, the answer for those is 'no' too.
So can Hubble see the flagpole on the Moon? The answer is no, it cannot. The highest resolution that Hubble can achieve is about 0.03 arcseconds [per pixel] using its Advanced Camera for Surveys (ACS) array of cameras. The smallest object on the Moon that Hubble could observe is about the size of a football field.
Detailed ACS info here (repeats the 0.03 figure; FWTW, ESA gives a somewhat smaller number of 0.025 arcseconds per pixel for the High Resolution Channel of the ACS.) Note that the newer WCF3 installed in 2009 has slightly lower resolution (0.04 arcseconds / pixel) but a wider range of frequencies.
If that source is not enough, here's another NASA page saying:
The Hubble Space
Telescope could just
make out a crater
100 meters or yards
across, the length of
a soccer field.
The 4ft flags themselves are clearly out of the question. Possibly Hubble could discriminate the 150 foot shadow though, in the right conditions, but it would be like half a pixel at best, so it would require a fair bit of interpretation (probably from multiple images, using SAR-like techniques.)
N.B.: it's been rumored, but only partly correct that Hubble is related to the tech used in spy satellites, i.e. that it's a spy satellite pointed upwards, instead of downwards. The mirror diameter of 'leftover' US spy satellites is similar to Hubble's though, but some details differ, e.g. the focal length; the 'spy' sats consequently have "a much wider field of view". The WFIRST space telly that was the made with one of those leftover 'spy' mirrors has however many more sensors (and higher res) than Hubble's, i.e. an array -- 18 sensors of 16 megapixels each; but the ultimate resolution is the same, although WFIRST takes like 100 Hubble-like images simultaneously [also on a different spectrum]. WFIRST is slated to launch in 2027.
James Webb has a larger mirror, but because it operates at lower frequencies... that doesn't improve its resolution, relative to Hubble:
Despite its larger size, Webb delivers about the same resolution in near-infrared light as Hubble attains in visible light. A telescope’s resolution, the amount of discernable detail, is proportional to mirror size, and inversely proportional to the wavelength of the light observed. For Webb to resolve the same level of detail at longer wavelength infrared light that Hubble achieves at visible wavelengths, its mirror needs to be proportionally wider.
Apparently Webb has a focusing problem, in that it wasn't designed to focus on objects 'this close', but on distant galaxies. It also technically orbits the Sun, and not the Earth. And because of its position at L2, Webb is actually farther from the moon than Hubble.
It's also not clear to me if the flag shadow would show in IR, the frequencies that Webb's sensor works at. It's also not possible to safely point Webb at nearby objects because that would at least temporarily 'blind' the ultra-sensitive sensors:
Because the telescope and instruments have to be kept cold, Webb’s protective sunshield is blocking the inner solar system from view. This means that the Sun, Earth, Moon, Mercury, and Venus, and of course sun-grazing comets and many known near-Earth objects cannot be observed.
(Fun factoid: "The sunshield gives Webb the equivalent sun protection factor, or SPF, of one million, NASA says.")
So, in theory, if you took the Webb mirror, a higher-res optical (not IR) sensor, and moved it back in earth orbit, it would be somewhat better at looking at the moon. But nobody is going to do that to see the shadow of a flag, on a few pixels, when you can send a spacecraft to orbit the moon and see it from there, like a spy satellites sees stuff on Earth (theoretically more clearly, because the moon lacks an atmosphere--but the LROC images from 2012 were not exactly impressive--the flag and its shadow were like 10 x 3 (blurry) pixels--LROC has 0.5 m/pixel best resolution, it seems.)