I'm not taking anything away from his MOH, Teddy Roosevelt was a cool dude. I'm sure it would have been cool to hang out with him over a few shots of whiskey or at the shooting range. However, I think you need to understand what medals the US had at that time and how they were handed out.
IIRC when the Continental Army was founded they did not want to emulate the European method of awards, many of which were questionable, political and gaudy. Originally there were no awards until George Washington instituted a few of which I think he only handed out three.
The Silver Star was first awarded in 1932, Navy Cross 1919, Bronze Star 1944 retroactive to 1941, Distinguished Service Medal 1918.
The Purple Heart was a general award from 1780 until 1932 when it was designated for wounds for all services. It's evolution is complicated: link
During the Civil War, Philippine Insurrection, Boxer Rebellion, and WWI the MOH was about the only medal for battlefield action and bravery the US had. After WWI it was determined that there were different levels of accomplishments and bravery and they embarked on other awards with the MOH being retained as the highest.
Look at the ribbons on WWII vets and you'll find maybe two rows. Now look at some Colonel or General today that spent minimal or no time in a combat zone and you may see up to seven rows. I'm not saying anything is wrong with that just that as time progressed the military has decided that non-combat awards and where you were stationed and actions you took part in are important too. Awards are good for morale too. I just hope they don't overdo it like some N. Korean general.
Also, some awards like the Bronze Star can be awarded for admin accomplishments or in combat. If awarded for combat action there is a "V" for "valor" on the medal. The Silver Star and MOH are only for combat so do not have a "V" device on them.
Recommendations for awards in combat during WWII, Korea and Vietnam were complicated. You needed a number of witnesses and sometimes the award was written up on a piece of C Rat cardboard in the rain or snow in the middle of combat only to be lost or the witnesses killed. Then there was a board of REMF's that reviewed the awards and on many occasions downgraded them even though they were not there or interviewed the witnesses. That's just the way it is.
Today the MOH seems to be awarded for self-sacrifice and not racking up a high number of kills. In the last 20 years since there is a high percentage of Spec Ops that cannot be publicly documented and many serviceman that deserve awards are not being awarded. I think recently Spec Ops and Delta Force members were publicly given the awards they deserved.
I have a close relative that was recommended for the Bronze Star with "V", 3x Purple Hearts and a Navy Commendation Medal but didn't receive any because his command said, "We can't document those actions." At least his DD-214 shows one wound so he gets VA medical benefits. He said he didn't enlist in the Marines for medals. He said all he got was a form letter from the Commandant thanking him for his service. He said he's cool with it and is very low keyed about the whole thing. He's had the same thing happen to some of the guys he served with. One guy he served with had a Navy Cross recommendation down graded to an admin award.
When I was in during the VN era if we saw an enlisted Marine with a Bronze Star we assumed that if he was an officer he would have gotten a Silver Star. I'm not taking anything away from officers leadership and bravery, that's just the way it is in the Marines.
During VN if you got 3x PH's you got a free ride home. When things were hot and heavy in I Corps in 1968 guys were getting multiple non-lethal wounds while at fire bases like Camp Carrol and the Rock Pile. The Marine command changed the PH award criteria that a "wound" only counted if you had to be medivacked to a hospital ship in the China Sea and that had to be approved by your CO. If not the fire base would have been almost empty. "Semper Fi mac" as we used to say.
Wolfhag