The Tennessee Central was an unlucky little railroad for much of its history. When it was formed in the early 1880s, many of the South's railroads were firmly entrenched and didn't take kindly to any newcomers. The L&N and the NC&StL kept the TC from using Nashville Union Station, and the TC began its history of being plagued with financial woes.
The TC's founder was the charismatic and rutless businessman and politician Jere Baxter. When money proved difficult to find in Tennessee, Baxter went to St. Louis and raised it. The TC was deprived his leadership when he died in a hunting accident in 1904. The TC fell into receivership twice and had poor health throughout its history, before finally being split between the Illinois Central and Southern Railway in 1968.
But what if the TC had managed to become a well-run, profitable little coal hauler like the Virginian? One idea I had was Baxter receiving the Democratic nomination for governor in 1890 (which he sought), winning the election, and using his position to help the TC out.