It is possible (and even slightly plausible) to have a soldier who served in Grenada, Panama, Desert Storm, Somalia, and some portion of the GWOT and actually still in service. Said individual would either be a very senior Sergeant Major or a 4-star at this point.
But by my reading of the reg, they would only have a CIB (1st award) with one star (2nd award.) Grenada, Panama, ODS, and Somalia are all in one group by my reading, so no repeat awards for doing more than one.
Note that any enlisted soldier would have to be an 11B or 11C, as there were no mechanized (11M) units involved in Grenada or Somalia. There was one mechanized battalion (4-6 Infantry, 5ID) that took part in the Panama operation. And any such individual would have been an 11Z (1SG/CSM) by the time GWOT rolled around. (It would also be possible to have been an 11B/C in Grenada, then transitioned to SF 18-series for one or more of the later conflicts.)
I think most of the later conflicts get lumped into a group only qualifying for a single award because Big Army didn't fell like it was right that a soldier who, for example, served in the 1st Infantry Division in WWII and fought in North Africa, Sicily, Italy, and France, would only qualify for a single award despite a huge number of days in combat, while someone who spent just a few weeks at most getting shot at in Grenada and Panama would qualify for 2.