For 2007 to 2008, Hartford (Connecticut) gained more college educated workers than Chicago. That's at the CSA level. Minneapolis also did better than Chicago on that score. On the balance, Pittsburgh benefited more than 2.5 times from net talent migration. Those numbers don't take into account differences in population. Chicago is hitting way below its weight class.
Concerning Chicago's heavy investment in its core, the returns are lousy. Its central city lags behind both downtown Pittsburgh and Minneapolis in terms of educational attainment rates. Chicago even trails Minneapolis in terms of per capita income.
There's more to talent than college degrees. Chicago is still a primary immigrant gateway. But that has little to do with urban policy. What Chicago does control has largely failed to generate dividends.
The distance between Midwest top-dog Chicago and Pittsburgh/Minneapolis remains great. However, those two cities are seeing excellent returns on their investments. Pittsburgh in particular is a fast riser in both per capital income and educational attainment. The region also has a lot of ground to make up. Not only is Chicago falling back to the pack, Pittsburgh is surging forward. Enough to upset the global urban hierarchy? No.
The fear is that Chicago is slowly imploding, the global city status a house of cards. In terms of talent, I think the concern is warranted. Relative to its Rust Belt cohort, Chicago is a weak performer. Nationally or globally, the tale of the tape must look even worse.