It's interesting to note that one of the biggest criticisms about him was that he would force companies to sell themselves to him or be put out of business by his monopoly power. Now, 100+ years after, it's still a business practice. I know it happened when Amazon bought diapers.com. Amazon threaten to start it's own diaper service and put them out of business, if they did not sell. Was it a smart business practice from Amazon's view or was it corrupt? I guess it's up in the air since it's still happening.
If you read Teddy Roosevelt's bio you get a view of what politics and business where at the time.