Red States have lower wages, higher poverty rates, lower levels of education and shorter life spans on average than Blue States.
I wonder if they are tired of all the winning?

We should all keep in mind that there's a bit of "being born on third base and thinking you've hit a triple" going on here.

For most Red and Blue states, the former are poorer than the latter today because they've always been poorer than the latter. Mississippi isn't poorer than New York because NY implemented more progressive economic policies over the last century. Mississippi's always been one of the poorest states in the union, and New York's always been one of the richest - because Mississippi started off as a primarily agricultural state, and New York has always been the home of the largest centers of trading and finance in the country.

The division between Red and Blue states, particularly when it comes to economic policy, is of relatively modern origin - certainly not much older than the 1950's. The relative ranking of our rich and poor states mostly pre-dates that:

apps.bea.gov: PDF document

The states that were really, really poor in 1950 are mostly still the same ones as today. The 10 poorest states back then were Mississippi, Arkansas, South Carolina, Alabama, Kentucky, Tennessee, West Virginia, North Carolina, Louisiana, and Georgia. The 10 poorest states today are nine of the same ten - only New Mexico has swapped in for Georgia.

en.wikipedia.org - List of U.S

And while I couldn't find a good table with incomes going too far back, the states that have had the greatest level of income growth since 1984 are: Oregon, South Dakota, Utah, Tennessee, Nebraska, Idaho, Iowa, Pennsylvania, Washington, and Rhode Island. A pretty long time frame (nearly four decades), and a pretty solid mix of both Red and Blue states.

www2.census.gov - Historical income households