Pictures and firsthand reports from voters who showed up to cast their ballots early at the Shenandoah Library on Friday, May 30, for the special election to fill the vacant District 4 seat came with an unexpected twist: former City of Miami Commissioner Alex Diaz de la Portilla was spotted actively campaigning outside the polling location — not just for himself, but apparently also for Jose Regalado.
According to multiple witnesses, Diaz de la Portilla was seen walking elderly voters into the precinct, reportedly encouraging them to support Regalado on their ballots. His presence and behavior raised eyebrows, especially as he appeared to blur the lines between his own campaign for Mayor and active involvement in district 4 race.
Meanwhile, his sister — a Miami-Dade County employee — was also observed outside the Flagler Library, the other early voting site that same day, engaging voters and urging them to vote for Regalado.
Throughout the day, Diaz de la Portilla was also seen chatting with prominent figures closely tied to Regalado’s campaign, including Raquel and Tomas Regalado, as well as his former chief of staff from his time at City Hall, a city of Miami firefighter. While the Miami Police union has backed Ralph Rosado, the Miami Firefighters have backed the younger Regalado.
Alex Diaz de la Portilla is no stranger to the political spotlight. A former state senator, state representative, and Miami city commissioner, he was removed from office by Governor Ron DeSantis in 2023 following criminal charges. Although the Broward State Attorney’s Office dropped the case earlier this year, his re-emergence at polling sites — particularly in support of Jose Regalado — is sure to prompt speculation among voters about alliances, influence, and what’s really at stake in this election.
Is this simply political camaraderie, or does it signal a deeper alliance between two political dynasties with long histories in Miami? Voters will have the final say on June 3rd.
