Once-powerful Sarasota developer Henry Rodriguez reshapes, refocuses life

Henry Rodriguez grew up poor in Washington Heights, a tough New York City neighborhood in Manhattan bordering the Bronx. His parents — a seamstress and a building superintendent — were Cuban immigrants. 

That should have made his top-of-the-world success story even more satisfying. 

This is when, in his 30s and 40s, he developed dozens of commercial and residential real estate projects in Sarasota; donated and raised millions of dollars for politicians, including both Charlie Crist and Rick Scott for their gubernatorial runs; sat on and chaired multiple boards; and acquired many of the trappings of wealth, down to a Gulf-front mansion on Casey Key so fancy it had a nickname, Casa Salamanca. Prior to real estate, Rodriguez had success in technology sales and in investing in telecommunications firms, saying he was a multimillionaire by the time he was 30.

But Rodriguez was far from satisfied with his rich successes — though he didn’t realize it at the time. He recalls the day, in 2001, when he was handed a check in an attorney’s office for more than $10 million from Walmart. He had just closed on a deal to sell a large parcel in Osprey, south Sarasota County, to the retail giant. “I was ecstatic and full of dopamine and when I got in the elevator alone I jumped higher than Michael Jordan,” Rodriguez told me during a virtual interview in July while in Ibiza, Spain. “That lasted about three days. Then I was back looking for the next deal.”