Four Endorsements, Plenty of Questions

In an unexpected move that immediately drew public criticism, The Greater Key West Chamber of Commerce, announced on August 3 that it was endorsing four candidates in city elections.

The announcement arrived as vote-by-mail ballots were already being returned and early voting was beginning, prompting questions about the Chamber’s process, timing, and decision to endorse two candidates who currently serve on its board.

The Greater Key West Chamber of Commerce, commonly referred to as the Key West Chamber, is a 501(c)(6) business league representing more than 500 businesses and organizations.

The endorsements were approved by the Chamber’s Board of Directors rather than through a vote of its full membership and were first widely reported by Keys Weekly. The Chamber selected:

• Incumbent Mayor Danise “DeeDee” Henriquez for Mayor of Key West, 
• Mark Rossi for City Commission, District II
• Juan Llera for City Commission, District IV
• Greg Sullivan for City Commission, District V

The announcement drew divided reactions online. Some Chamber members reported they had not been consulted or informed that endorsements were under consideration. Several candidates questioned the transparency of the process, particularly because Rossi and Sullivan are current Chamber board members. A few praised the organization for publicly taking a position in closely watched local races.

The Chamber of Commerce first emailed a letter signed by President Amber Shaffer to its members earlier this week. In it, Shaffer described an election that had become extremely divisive and revealed that after the Chamber's Candidates Forum, which occurred back in June, its Board of Directors discussed "whether we should take a stand in this election."

The answer was yes.

An Exercise in Best Judgement

In an emailed response sent by Executive Director Kerry Baker on behalf of the Chamber, the organization said its Board of Directors is elected by the membership and entrusted with making decisions on its behalf.

[Author's Note: It now appears that this exact statement was supplied to multiple publications and leaves certain questions unanswered]

“Like any elected governing body, the Board is sometimes required to make difficult decisions that may not reflect the views of every individual member,” the response read. “Its responsibility is to exercise its best judgment in the interest of the Chamber and the business community it represents.”

The board was said to have begun discussing endorsements early this year, citing the contentious nature of the election and what was described as “repeated derogatory comments and references directed at the Chamber, our Board and many of our members.”

Although City Commission candidates Mark Rossi and Greg Sullivan are Chamber directors, Baker said neither was present for the endorsement discussion or vote. She explained that endorsements were approved through a motion during a board meeting but did not disclose when the vote occurred, whether the candidates were considered separately or as a slate, or what the vote tally was.

While City Commission candidates Mark Rossi and Greg Sullivan are current Board members, neither were reportedly present for the discussion nor vote on endorsements. The decision was made by a motion that passed during a Board meeting. And given that the Chamber's mission is focused on the City of Key West, the Board's endorsements were limited to City of Key West elections.

“The Board’s decision was reached through thoughtful discussion, careful consideration, and a commitment to the Chamber’s mission and the business community it serves,” the response continued.

Follow-up questions as to the “derogatory comments and references” that influenced the board’s deliberations have not yet been answered by publication time but will be included here if provided.

Survey the Full Membership

District II Commissioner Sam Kaufman, who is challenging incumbent Mayor DeeDee Henriquez in what is viewed as the marquee race of the season said he respects the Chamber’s right to endorse candidates but questioned whether the board’s process adequately represented its membership.

"From the many Chamber members I've spoken with, many were unaware that an endorsement was even being considered and were never asked for their input," he said. "Given the diversity of businesses in our community, I believe it would have been more representative to survey the full membership before taking a position. The Chamber itself has used broad member input in the past on important issues."

Kaufman added that he has received support from numerous Chamber members and local business owners. He described his platform as pro-business, citing his positions on city spending, permitting, affordable housing, and environmental protection.

Long-Term Reputational Questions

Chris Massicotte, who is facing off against Greg Sullivan for District V, was initially shocked by the Chamber's move, especially since none of the other members who he spoke with were asked to weigh in on any endorsements. He thought the nonprofit would stay above politics.

Massicotte pointed out that he is a member of the Chamber through his Duval Street Media, LLC and maintains good relationships with both Shaffer and Baker.

"I met with them and I wanted them to understand who I was and why I was running. And I just didn't think they were going to actually endorse. And as a political professional," he said of his former work in consulting, "I would have told them that they are doing it wrong because you can't endorse two weeks out when you have people who have already voted and you didn't go through a process. And in their press release, they said, 'After our forum, we decided to. . .' Well, their forum was six weeks ago."

Massicotte focused particularly on Rossi’s and Sullivan’s positions as sitting Chamber directors.

"Whether or not they voted for it on this endorsement doesn't matter because they shouldn't be endorsing," Massicotte said of the Chamber's board.

Massicotte acknowledged that current rules permit 501(c)(6) organizations to engage in some political activity. His objection, he said, concerns the judgment and appearance of the decision rather than whether the Chamber was categorically prohibited from making it.

"I would've been more worried about the long-term reputation of my organization regardless of how this election goes. We will know in two weeks," he said of the local races, "but the damage that is going to be done to the chamber as a result of this is going to be felt for quite some time."

While he has not made any particular decision about his own membership, he has already witnessed several others publicly expressing that they intend to cancel theirs.

Just as Surprised

Mark Rossi, one of the Chamber board members who received an endorsement, said he and fellow board member Greg Sullivan were initially present at the meeting but left the room before the endorsements were discussed.

“Greg and I left the room, and then the rest of the board that was in the room discussed it,” Rossi said. “From my understanding, they took a vote and decided to endorse the business candidates they chose to endorse.”

Rossi said he learned of the decision a few minutes after leaving the room.

“I had no clue, okay? Not one. On my mother’s grave,” he said when asked whether he had any advance indication that the board was preparing to endorse him.

Rossi said he had reason to believe the Chamber would keep some distance between his candidacy and his position on the board.

"I had a problem with the chamber anyhow. When I first said I was going to run, they said that I had to be suspended."

Asked whether he viewed the endorsement as an advantage or as potentially more trouble than it might be worth in what could be a close District II race against Bobi Lore, Rossi described it as a bit of both.

"Fifty-fifty each way," he replied. "I kind of thought maybe people might kick a fuss about it, but at the same time, we got to represent the business community."

Rossi also said that, if elected, he would recuse himself from City Commission matters involving direct conflicts with his business interests. He said he had done so during his previous service as a city commissioner and vice mayor.

The Endorsed View

There is of course potential upside to all of this for some. At this stage in the voting process, any endorsement, especially one from an organization with name recognition and influence in the community, has the power to potentially sway remaining undecided voters.

Juan Llera, one of three candidates seeking the District IV commission seat, secured an endorsement over opponents Sarah Compton and Wayne Garcia.

He said he was grateful and honored, particularly because, as he understood it, endorsements had not been made by the Chamber in almost a century.

"As a candidate for City Commission, I am humbled by the Chamber’s confidence in me and remain committed to serving our residents, supporting our local businesses, and recognizing the employees who help keep our community strong," he said.

"Our local businesses are the backbone of Key West, they create jobs, support families, donate to local nonprofits, provide scholarships, and invest in the future of our community."

While Llera was admittedly away traveling somewhere through the Rocky Mountains, and thus unable to keep track of the discourse surrounding the recent news, he did receive a phone call from the Chamber's executive director notifying him of the group's decision to endorse several candidates, and that he would be among the select few.

"I did not ask any questions. I did however express my gratitude."