Alot of it's about opportunity. I think if you delayed Al'Qaeda's attack til Obama, he'd be seen as badass, too. The country'd also be far better off because it would've been handled by an administration up to the job instead of a buncha lamers whom went instacorrupt and used the excuse to try to turn us into a supercorrupt China.
TR did have his downsides, note - he was a warmonger, racist, and imperialist. War IS hell, as an earlier military badass had rightly pointed out. The Mckinley/Roosevelt Administration even betrayed a Filipino democratic revolution, presumably because it'd had the bad taste to choose a nonwhite leader. TR left the war simmering when he was 'in', too. Colonialism, BTW, was, in effect, worldwide Jim Crow. The infrastructure enhancements were put in to get troops and white businesses' goods in and out.