Meet the Trump-loving yacht lawyer who helped engineer DeSantis' New College takeover

A conservative South Florida lawyer who attended New College of Florida in the 1970s and frequently argues with liberal alumni on Facebook has told multiple people that he was a key player in the conservative takeover of the college.

Robert “Bob” Allen graduated from New College in 1978 with a bachelor’s degree in international relations and went on to establish an eponymous law firm with 16 attorneys. He handles superyacht transactions and other legal issues that arise in an industry dominated by the ultra rich.

Allen also has been heavily involved in GOP politics, running for Congress in 1990, working on President George W. Bush's legal team during the litigation over the 2000 election and securing appointments to various boards from Republican governors stretching back to Jeb Bush, according to a bio on his website.

Allen once served on New College’s board of trustees, and now is telling people he engineered Gov. Ron DeSantis’ overhaul of that board, which is drawing national attention because the governor is making New College a showcase for conservative higher education reform as he plots a presidential run.

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According to statements Allen has made to multiple alumni, shaking up New College’s board wasn’t on DeSantis’ radar until Allen raised the issue with the governor.

“If Bob is to be believed, he’s the one who brought it to DeSantis’ attention that there were vacancies on the New College board where he could move in there and do whatever DeSantis wants to do,” said Michael Armstrong, a New College alum who graduated in 1977, knew Allen socially when they were college students and recently spoke with him about the takeover effort.

Allen has been saying the same thing to other New College alumni.

“It was the furthest thing from DeSantis’ mind and he got DeSantis’ attention on it,” is what Allen told another New College alum, who asked not to be identified, adding Allen said he "singlehandedly got DeSantis to do this.”

Allen confirmed his involvement in a statement to the Herald-Tribune.

"As I began to wonder why the college’s leadership had been ineffective in managing its relationship with Tallahassee, I studied the situation and discovered there were several vacancies on the Board of Trustees," Allen said. "To preserve New College, I recommended the Governor fill the vacancies.  He did so..."

How much did Bob Allen influence DeSantis' actions at New College?

Regardless of Allen’s statements to alumni and the Herald-Tribune, the extent that he triggered the new board of trustees appointments, or was instrumental in making them happen, is unclear. College officials routinely interact with the governor’s office to fill board vacancies. The governor's office has not responded to a request for comment.

Many people who have interacted with Allen are certain he had some level of influence on the process, though, and that continues. Eddie Speir, one of the new trustees DeSantis appointed, said he and Allen have communicated frequently, that Allen as been "trying" to act as an adviser and that "I'd be foolish not to listen to him."

Allen declined to be interviewed in time for this article, and his statement did not go into detail about his role in the New College takeover effort. It mostly focuses on his concerns about the college's trajectory in recent years and belief that what's happening now will benefit the school.

"My personal goal is to see New College become the best college in America - the MIT of liberal arts colleges, so to speak," Allen said.

Allen and Armstrong have been active in a New College alumni Facebook group that has been buzzing with talk about the takeover effort. Allen reached out to Armstrong, a retired newspaper editor who lives in Alaska, randomly on a recent Saturday and they ended up having a two-hour phone conservation.

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Armstrong believes the phone call was part of a pattern of Allen contacting alumni to try and ease their concerns about what’s happening at New College.

“He called me and others because he wanted to tell his story: This is what’s really happening. This is why this takeover is going on," Armstrong said.

Allen is on judicial nominating committee with trustees chair Debra Jenks

In addition to alerting DeSantis to the board vacancies, Allen told Armstrong that he suggested a slate of new board members to the governor. The governor didn’t pick all of Allen’s suggested board members, Armstrong said, but some were appointed. Allen has connections to at least two trustees.

Allen has a child who plays tennis at the Bradenton school founded by Speir, and Allen encouraged Speir to apply to become a trustee, Speir said. Additionally, new board Chair Debra Jenks and Allen both are attorneys who serve on the Judicial Nominating Commission for Florida’s Fourth District Court of Appeals. DeSantis appointed Allen to the position in 2019.

Jenks has become the point person for the next phase of New College’s transformation. She negotiated a widely criticized contract with Interim President Richard Corcoran that pays him $699,000 in base salary, more than double what former President Patricia Okker earned.

Okker was fired by the new board members on Jan. 31 and Corcoran emerged as her replacement the same day. Some have speculated about whether Allen orchestrated board actions behind the scenes.

That speculation spilled into public view during a recent board meeting, when one of the speakers during the public comment period claimed Allen acted as the “liaison to install Corcoran.”

Allen lives in South Florida but was in Sarasota the night Okker was fired and Corcoran was floated as her replacement by Matthew Spalding, a DeSantis appointee to the New College board. Allen showed up at a restaurant where trustees were having dinner after the board meeting.

Allen sat with the trustees at the dinner. He was one of the few people there who wasn’t a trustee or college administrator. Trustee Ron Christaldi organized the dinner and paid for it.

"I offered to take all the trustees to dinner to get to know each other a bit personally," Christaldi said. "It was social, and not involving any New College business... It was intended to be a way we could learn each others background... Bob did attend that dinner. I don’t recall who asked, but a day before the dinner someone reached out to me and asked if he could join.  I simply said yes. A few trustee spouses also attended."

Before Okker was fired, Allen was on New College’s campus, where he met with Brad Thiessen, a New College administrator who was being considered as interim president until Corcoran was available, according to multiple people with knowledge of the meeting. The board later picked Thiessen to serve as interim president until Corcoran starts on Feb. 27.

Allen’s reported kingmaker role in the New College takeover effort hasn’t previously been disclosed.

The Herald-Tribune sent questions about Allen's involvement in New College's transformation to the governor's office, each of the new board members and Allen himself. Allen sent an earlier statement in response to an interview request, but did not respond later to specific questions, nor did the governor's office.

The Herald-Tribune asked board members if they spoke to Allen, whether he had been acting as an adviser, and specifically whether they talked to him about Okker's termination, Thiessen's designation as interim president or Corcoran's hiring as interim president.

Trustees Spalding, Speir and Mark Bauerlein sent responses.

"I only recall one conversation with Allen... a quick chat by phone welcoming me to the board and mentioning concrete things about committees and structure and schedule. I don't think anything specific about the presidency came up," Bauerlein said.

Spalding called Allen "a very dutiful alumni who is especially focused on maintaining New College’s traditions and unique teaching system."

"At no time did we discuss the matters you mention here," Spalding continued. "He is not an adviser as far as I know."

Speir said he had "a lot of conversations" with Allen and they've become friends. Speir spoke to Allen before he was appointed to the board, and subsequently. He said Allen lobbied to keep Okker as president and "I listened and then disagreed."

Asked if he spoke to Allen about appointing Thiessen, and then Corcoran, as interim president Speir said "perhaps."

"If we did talk (I don’t remember if we did), it didn’t matter because I had already set my mind on Corcoran," Speir said.

Asked how Corcoran's name was first floated to him as an interim president, Speir declined to answer, saying he planned to address that on his Substack.

Speir said Allen has been "trying" to act as an adviser but "it's been rocky."

"But I greatly respect him and his advice," Speir added. "If he and I can work things out, I think that we will have the perfect blend of mysterious (often chaotic) free thinking and organized orderly operation.  We are still trying to figure it out; at least, I am... Bob is passionate about NCF, well-informed, and a valuable resource that has served NCF in the past and now informally as an advisor.  I’d be foolish not to listen to him and violate my oath if I didn’t think and speak for myself."

Speir also said that Allen initially asked him to keep their relationship secret.

"Bob had asked that I not disclose our relationship early on," Speir said. "In business law about trade secrets, once said information is made public, the owner of those trade secrets can no longer hold their employees to those secrets.  That is legally proper and I believe the same is morally valid.  I hope Bob agrees."

Speir later followed up to say he wanted to clarify those remarks, and said that Allen "is not trying to silence me."

Those who know Allen say he always has been interested in politics and power. He was head of student government at New College. Armstrong said Allen is the son of a diplomat who “grew up overseas” before arriving at the college.

Armstrong lived in the same apartment complex as Allen near the New College campus, and recalls talking to him at parties.

“I have memories of chatting with Bob at Palm Court parties,” Armstrong said, referring to New College’s signature social gatherings. “It was the kind of place you could interact with a lot of people not just academically and socially, but we’d have these intense after dinner conversations where we’d talk politics.”

Armstrong’s recollection of Allen is that back then he and a close friend were “Jimmy Carter Democrats.”

These days Allen is an ardent supporter of former President Donald Trump and DeSantis.

Allen’s Facebook page is full of conservative commentary.

“Trump didn’t lose ‘fair and square,’” he wrote in one post after Trump lost the 2020 election, adding: “Whatever Trump’s imperfections, on a fair playing field he would have won.”

In another post, Allen says Trump has been the victim of “a constant witch hunt” and adds “Trump 2024!”

Allen predicted that Trump will be the GOP presidential nominee in 2024 “and he will be OUR president.” He also praised DeSantis.

“I remain 100% Trump and 100% DeSantis,” Allen said in the post from November. “America needs Trump in 2024 and DeSantis in 2028 and 2032.”

Allen relentlessly pushed his political beliefs in the New College alumni Facebook group, frequently sparring with other alums. Some say his actions amounted to “trolling” and aggressive behavior they found off-putting for an older alum who sometimes was engaging with much younger graduates.

“He has always been like a lightning rod on the forum,” said New College alum Grant Balfour, who moderates the Facebook group. “He really loves a controversial debate and probably sees himself as a spokesperson for a particular voice in the culture war.”

According to Balfour, Allen was banned from the Facebook group Thursday for the second time. The latest ban was the result of Allen’s comments about pronoun use. It violated the group’s code of conduct, which Balfour said boils down to not being a jerk.

“He posts a lot, and he posts a lot knowing he’ll get a reaction,” Balfour said.

Allen has long believed New College is too liberal, according to alumni who have spoken with him and observed his comments on the Facebook group. Banning him from the group could reinforce that belief.

Yet while Armstrong disagrees with many of Allen’s views, he doesn’t doubt his sincerity, nor does he doubt that Allen believes he has the best interests of the college at heart.

Armstrong’s impression is that Allen is “well-meaning” and deeply believes New College “is a valuable education experiment that should be protected and saved, and here’s an opportunity.”

Armstrong believes DeSantis is just using New College “to promote himself for president.” He doesn’t think Allen is simply trying to score political points, though.

“I want to give Bob the benefit of the doubt,” he said.

This article originally appeared on Sarasota Herald-Tribune: Trump and Ron DeSantis backer Robert Allen led New College makeover