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Off course? What's happening at Charlotte Harbor National?

Bobcat Trail households say they've lost more than $2 million

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The grass is about a foot high at Charlotte Harbor National Golf Club since the Bobcat Trail course closed its doors Aug. 25 — except for the putting greens and tees, which have turned brown.

Rich Smith III

Rich Smith III

Rich Smith III told The Daily Sun in August the course was closed temporarily, preparing for season. He told residents it would reopen, but that hasn’t happened.

The phone number for the golf course is “temporarily unavailable.” Its social media pages are either down or not updated in months.

Smith, at one point, was the owner. His involvement is still apparent, his title unclear.

Bobcat Trail resident Doug McNamee reacted to Smith’s claim the course would reopen in 15 days.

“That’s ridiculous,” McNamee said.

The course could take months to restore. The putting greens are overrun with weeds; the grass hasn’t received fertilizer, McNamee said.

McNamee is among those who say they can document deceptions told by Smith. They believe they have lost $2.6 million they lent Smith.

Smith’s attorney has said those loans aren’t due for four more years.

Ellen Smith

Ellen Smith

One of the deceptions, they say, is Smith suggesting his wife has no role in running the business. The involvement of Ellen Smith, 50, startled them when they learned she served jail time for embezzlement in Michigan in 2002.


Smith’s debt is providing openings for his creditors. Until Oct. 15, he and his company, Cloud Ten! Marketing Group LLC, were delinquent on Sarasota County taxes to the tune of $159,625 for 2019 and 2020 property taxes. He owed $6,593 in tangible property taxes. Outside investors bought the 2019 tax certificates; if taxes remain unpaid, the Clerk of Courts could auction it in spring 2022.

On Oct. 4, two lenders filed suit against Smith and his limited liability company seeking immediate repayment of a $100,000 loan and mortgage on the golf course.

While the newest plaintiffs are Bobcat Trail residents William and Vivianne Dillon, 69 households in Bobcat Trail have chipped in money to cover legal expenses, McNamee said, noting nine of them had already lent Smith $100,000 each. The couple says they hold a mortgage for the golf course.

All involved want to take control of the 369 acres of rolling fields that anchor the subdivision.

The lawsuit and foreclosure by the Dillons demand Smith repay the loan; otherwise, the property would be sold or the Dillons could take possession of it.

William Dillon declined to speak on the record. The Dillons are part of a group of 13 resident households who lent Smith $1.3 million in 2017 to buy the course.

Smith and his attorney, Ian Horn, said the loan from the residents does not come due until 2025. Lenders point to the long delay in paying taxes and to maintain the course as reasons to call in the loan early.

On Oct. 15, the delinquent property and equipment taxes for the golf course were paid — by someone, Sarasota County Assistant Tax Collector Sherri Smith told The Daily Sun.

“We hope every business is successful,” Sherri Smith said.

It’s unclear if the delinquent state sales tax bill of $176,321 has been paid. The Florida Department of Revenue said that information is not public record.

Bobcat Trail residents remain concerned. McNamee asked who paid the latest bill.

“Where did the money come from? It’s got to be from somebody else,” he said.

Paying property taxes may remove the ability to call in a mortgage early.


There have been many creditors in line for money from Smith and his enterprises.

One debt shows up in Michigan courts and is tied to the criminal case against Ellen Smith from 2002.

The Smiths both still owe a company $148,379 according to a court clerk in Van Buren County, Michigan. Ellen Smith was convicted of embezzlement from the small Michigan firm.

They have paid $71,620 since 2003. Although Ellen Smith alone was convicted of a crime, she and Rich Smith were both ordered to pay restitution.

Sarasota and Charlotte County courts have several lawsuits demanding paying of bills related to the golf course. A few have been paid.

Those not reporting payment:

• October claim filed by Island Hotel Company demanding $378,686.

• Yamaha, seeking payment for golf carts.

Charlotte Harbor National Golf Club3.jpg

A worker for Double Bogey out of Sarasota loads a golf cart onto a carrier at Charlotte Harbor National Golf Club at Bobcat Trail on Aug. 5.

• Harrell’s Inc., seeking payment for turfgreen projects.

• Plum Creek Technology, seeking paying for the hole-in-one technology. A court ruled in 2020 that Smith defaulted on a payment of $11,991.

• PNC Financing, seeking payment and repossession of equipment.

• September default ruling for Lynch Oil for $9,871.


Four years ago, Smith impressed the group as the golf pro at the course with his commitment to turn Charlotte Harbor National into a premier location. And in the first year, McNamee said, the course looked great.

McNamee said 13 households lent Smith money to help him buy the course. Most of the money came from a $2.6 million loan from Celtic Bank.

Smith had an idea for the club — and for golf courses around the country.

It was a concept to make golf more exciting, pull in more players and make money along the way.

The plan was to tell golfers they would win $10,000 if they hit a hole-in-one. There would be cameras and new technology needed.

The group of 13 decided to invest again, between $50,000 and $200,000 each this time. Smith gathered a group of experts to make the plan happen.

It started out in 2018 as Next Cloud, then SKYiGolf, then Ace Oasis. The first two Smith has labelled as bankrupt. The last is still an operating website where it seeks recommendations for courses to be involved; phone numbers associated with it, though, are not working.

Those involved in lending believe the hole-in-one concept has broken down. They don’t know what happened to their investment.

And Smith isn’t talking.


In early 2021, Smith filed for voluntary Chapter 11 bankruptcy in U.S. Bankruptcy Court for Florida Middle District for the golf course, not the hole-in-one enterprise.

In filings to the judge, he named two causes for the course’s current situation: the pandemic, and his claim that repairs and upgrades to the course in 2019 were done incompetently, resulting in “diminution of the Debtor’s business.”

With Yamaha Leasing seeking to repossess his golf carts, he explained, he needed bankruptcy protection or he would be forced to cease operations. By the end of August, he successfully exited bankruptcy against the wishes of Bobcat Trail residents who lent him money.

Smith asserted in court filings a third claim for the course’s failure: It was sabotage by club members and residents who seek to lower the price of the course so they can buy it.

“Mr. Dillon and his cohorts, including Mr. McNamee, have engaged in a deliberate, concerted and aggressive effort, from a least early in 2020, when the COVID-19 Pandemic began, to interfere with and devalue and destroy the Debtor’s Golf Course business,” a court rebuttal reads. “The reason for the efforts of Mr. Dillon, Mr. McNamee and their cohorts was to devalue the Debtor’s Golf course business to the extent they could purchase it very cheapily.”

McNamee told The Daily Sun that’s not a plan.

“We already bought it once,” he said. “We’re not going to buy it again.”

McNamee was referring to the first $100,000 that 13 residents each loaned Smith in 2017 to buy the course from an earlier owner they did not think was doing enough to develop the course. That money — along with other loans, including $2.6 million from Celtic Bank in Utah — allowed Smith to purchase the course.


Residents spoke out at a September Home Owners Association meeting.

McNamee said he feels responsible for urging others to invest — and for urging many people who are not wealthy to buy lifetime club memberships of $45,000. These are memberships they now can’t use.

Those involved talk of betrayal. The 13 families who lent first $1.3 million, then $1.4 million, were disturbed to see Smith spend money lavishly in the early days — inviting investors in a new plan on a costly trip to a resort in the Bahamas.

“During the first year of owning the course, he bought all the founders presents, had dinners; we all told him the presents were not necessary, and put on lavish parties with entertainment. We all attended all his parties and paid a large fee to attend,” Bobcat Trail resident Betty Bennett wrote, adding she began to worry Rich Smith was using the money they had lent him irresponsibly. “Now he is blaming us, the founders, for his failure.”

Smith, in an earlier email to The Daily Sun, suggested people are out to get him.

“There is a lot of false (libelous) information you have been provided by people who are intentionally trying to hurt us,” Smith wrote.

To the judge, he accused Dillon and McNamee of trying to keep people from patronizing the bar and restaurant. McNamee denies this. Smith told the judge McNamee lied when he claimed Smith was filing for bankruptcy just to avoid a $500,000 bill to the Atlantis Resort & Casino in the Bahamas.

“Neither Mr. Smith nor Next Cloud was ever indebted to $500,000 to a hotel in the Bahamas. {Or indeed for ANY amount.}” it said.

However, that hotel recently filed suit saying Smith and the LLC cost it $497,032 in 2019 after canceling for 361 people. The company discovered Smith failed to mention them as creditors in his bankruptcy. Seeing he was out of bankruptcy, it is demanding $378,686, giving Smith credit for bookings it was able to make at the last minute to cover its losses.

Smith’s attorney, Ian Horn, of Brandon, refused to speak on the record on the cases Oct. 14.

He provided a statement after Smith canceled an Oct. 4 meeting with The Daily Sun. The email also threatened legal action against journalists involved in the story and The Daily Sun.

“In lieu of the meeting between you and Mr. Smith today please accept this written response regarding your inquiry. Let me be abundantly clear that the material you presented to us is false and libelous. We will not hesitate to take legal action against you personally as well as your newspaper should you print anything inaccurate, misleading, or libelous. Additionally, the false information provided to you is based on someone else’s personal agenda and is not germane to the golf course and its operational status. It is also worthwhile to note that Charlotte Harbor National Golf Club is a privately held company with NO INVESTORS. The so-called investors you referenced are LENDERS, whose notes are not due until Fall 2025. Being a privately held company we have no obligation to share intimate details about the operation. Please see below statement on behalf of Charlotte Harbor National Golf Club. ‘Charlotte Harbor National Golf Club is temporarily closed. The financial impacts of the pandemic as well as attempted sabotage and interference from a resident for personal gain have us evaluating and assessing the business model going forward. We hope and are optimistic to share good news with our customers very shortly. We are proud of our efforts during the pandemic which include delivered groceries, single rider golf cars, and an abundance of safety provisions while providing socially distanced enjoyment to many while options have been limited due to the pandemic.’”

McNamee scoffs at the notion of the pandemic as a cause, noting golf skyrocketed in 2020 as one of the remaining acceptable pastimes. Golf Datatech showed nationwide rounds in 2020 increased 13% by November 2020 over the same period in 2019 — the year before COVID-19.

McNamee says the group should have used an attorney when they agreed to loan Smith money originally. The group has hired attorney John Chapman, of Sarasota, to represent them in the Dillon’s litigation against Smith and Could Ten!

They trusted Smith mainly because he was a member of the Professional Golfers’ Association, McNamee said.

McNamee wants the PGA to remove Smith’s membership. He sent a three-page letter to PGA Membership Director Tom Brawley citing Smith’s alleged violations. Brawley asked McNamee to wait for a final judgment against Smith. North Florida PGA Director Steve McMillen said he could not comment, aside from saying Smith earned his membership in Michigan, not Florida.

“We realize our money is gone,” McNamee wrote. “Our objective is to prevent Mr. Smith from ruining another community as he has done to ours. This man must be stopped, and you and your organization have the ability to prevent him from foisting his schemes on others.”

Weeds on the tee green

Tall weeds sprout from a tee off green at Charlotte Harbor National Golf Course.

McNamee told The Daily Sun he sometimes thinks that Smith started out well-intentioned, and that he let his finances get out of control. But then, McNamee says, he remembers that Smith let his wife manage the course, knowing she was a financial felon.

“That’s the conflict that I have,” McNamee said. “That’s the conflict we all have.”


Ace Oasis is Smith’s plan — on its third name — that excited golf pros and Bobcat Trail residents, with golf pros becoming employees, and residents, lenders.

The business concept: Smith would arrange for participating golf courses to offer a $10,000 award to anyone who gets a hole-in-one.

Golf courses across the country are sought to sign on. They would pay Ace Oasis a fee per round of golf. In addition to attracting more players, the courses would receive the newest golf course management software.

Smith’s company would pay software and camera companies and also a per-round fee to Lloyd’s of London for a big insurance payout.

The hole-in-one deal would all be done based on trust, unless Lloyd’s of London considered it suspect, in which case it would investigate the books, insurance agent Doug Donley said.

Donley, president of Advantage Hole In One, said he asked Smith when the program would start, and Smith kept telling him soon. But nothing ever happened, Donley said. He also said Smith never told him the plan was for golf courses across the country. Donley assumed it would only be the North Port course.

No one seems to know what happened to the SKYiGolf investments. Two participants say they were financially damaged by Smith.

Bob Baldassari, a golf pro, said he was hired by Smith to be the chief operating officer for Ace Oasis.

At first, he was paid, Baldassari told The Daily Sun. One thing that bothered him, however, was that neither he nor the chief financial officer were allowed to write a check, look at the books nor sign a contract. He felt cut off from the operation’s finances.

“He always said, ‘Ellen takes care of that,’” Baldassari said of Smith’s wife.

Email from Ellen Smith

An email from Ellen Smith states her position as general manager of the Charlotte Harbor National Golf Course and her involvement in the business. It is contrary to statements to a bankruptcy judge made by Smith’s husband Rich Smith III, that she was not involved in the management of the business. Ellen Smith has a felony conviction of embezzlement.

Rich Smith told Baldassari that Ellen Smith would be doing the tasks that Baldassari thought he would have done for his salary. Baldassari also felt Smith ignored his professional advice, such as take it one step at a time.

Smith later insisted to the bankruptcy judge his wife had no role to play in his business.

Eventually, Smith stopped paying him, Baldassari said, and he moved on.


Another Ace Oasis enthusiast was Mike Reimer, owner of Pheasant Ridge Golf Club in Pennsylvania. Reimer and Smith spoke on the phone at length, and their personalities seemed to gel.

One night in January, Reimer received a call from Smith.

“He’s literally crying,” Reimer recalled.

Smith said he needed $22,500 to make the next payroll. Reimer agreed, but he did not like what he was hearing. Later, Smith said it was $85,000.

“I said: ‘Rich, what cloud are you on?’”

He recalls Smith saying something about an equity position.

Reimer balked, and they settled on $25,000.

He flew down to North Port unannounced to meet with Smith and see what he was like in person. Smith put him off for several days.

“He was always in a meeting with Ellen,” Reimer recalls.

Soon after the loan, Reimer received a release, separation and nondisclosure agreement from Smith. It included the terms of loan repayment. It left Reimer with the distinct impression the nondisclosure was a requirement of repayment.

The requirement states they would unwind their business agreement and Reimer would never disparage Smith nor his business.

“Both parties also agree that, unless otherwise required or permitted by law, you shall not disclose the existence or terms of this agreement, including but not limited to the amount you received in exchange for signing the agreement,” it said. “Should either party default on any of the conditions of this Agreement, the contract will be immediately terminated with notice from either party.”

Reimer, outraged, refused to sign. Worried about the Ace Oasis deal, he demanded Smith give him the name of the insurance agent.

Donley told him Lloyd’s of London had not agreed to any payments. Reimer said he assumed he would have to pay the $10,000 should any of his golfers get a hole-in-one. Donley has said he would not have required an upfront payment, just payment by the week of play.

Reimer backed out of Ace Oasis — and told other golf course management firms his experience.

In an email to The Daily Sun, Smith names Reimer as one of the people attempting to ruin his reputation.

Reimer said he considers himself lucky to have walked away having lost only $25,000.


As the original 13 lenders investigated the man they trusted, they learned of his wife’s conviction for embezzlement in Van Buren County, Michigan.

Rich Smith says it is irrelevant to the golf course situation.

Ellen Smith was married to Rich Smith at the time of prosecution. About $22,000 of the money she embezzled was used for their marriage ceremony, Michigan attorney Ronald Baylor told The Daily Sun.

“We paid for their wedding,” Baylor said, wryly.

Baylor represented the victim, Bloomingdale Telephone Co., in the civil restitution case. He was also present in the criminal case.

Ellen Smith was convicted of embezzlement, but both were named in a $220,000 repayment plan that required garnishment of wages and forfeiture of their home and a car.

“It was a classic embezzlement scheme,” Baylor said. “It’s like a nightmare coming back to me … Some of the details I could probably cite in my sleep.”

Bloomingdale Telephone Co., a company of 30 employees, suddenly found it had no collateral for a large loan. The small business nearly folded because of it.

“They had a big impact on that company and that company almost disappeared,” he said.

In his petition to keep Smith in bankruptcy, McNamee raised the issue of a convicted felon handling finances of the golf course.

Smith slams McNamee.

He “maliciously, deliberately and without legitimate purpose attempts to embarrass, humiliate and injure Mr. Smith’s wife Ellen,” Smith’s statement claims. “Mr. McNamee refers to an occurrence that is more than 21 years old. Ellen Smith is not responsible for operating the Debtor, nor does she make financial decisions with respect to the Debtor. The matter is completely irrelevant to Debtor.”

The filing is signed with the typed name of Ian Horn. Horn refused comment on that situation in a Oct. 14 phone call from The Daily Sun.

In the same letter to the judge, Smith calls William Dillon a convicted felon.

Dillon was jailed six months for insider trading after pleading guilty to wire fraud in 1988 at the age of 33.

Dillon, a broker, was paying $10-$30 for advance copies of Business Week magazine from workers at a printing press. He would get it on Thursday mornings but the publication was released on Thursday evenings, according to a 1988 Washington Post report.

Dillon admitted he bought securities for more than 100 companies praised in a weekly column, then sold them after the magazine was released and prices went up, the Post reported from court documents.

McNamee debated Smith’s insistence that Ellen Smith was not involved in the business.

Email from Ellen Smith

An email from Ellen Smith states her position as general manager of the Charlotte Harbor National Golf Course and her involvement in the business. It is contrary to statements to a bankruptcy judge made by Smith’s husband Rich Smith III, that she was not involved in the management of the business. Ellen Smith has a felony conviction of embezzlement.

“Your honor, Ellen Smith is the General Manager of CHNGC,” McNamee wrote in court documents. “She handles all the finances of the organization and is a key decision maker in this closely held business.”

McNamee provided The Daily Sun with an email from Ellen Smith about golf course business using the company email. Her email signature includes the title “General Manager.” McNamee also has a score card with Ellen Smith’s name printed as general manager.

Charlotte Harbor National Golf Course score card online

Charlotte Harbor National Golf Course score card shows the name of Ellen Smith as general manager. Her husband, course owner Rich Smith, has said she was not involved in running the course. She was convicted for embezzlement.

The judge ruled against McNamee and Dillon, allowing Smith to exit bankruptcy and giving him a chance to borrow more money.


Late this summer, Bobcat Trail residents saw surveyors on the course. They fear a developer will take over the land and build homes similar to the former Sabal Trace golf course in North Port.

Anne Jacklin, of Las Vegas, acknowledged in an Aug. 31 email to club members she ordered the survey. Jacklin owns a consulting company called Performance Out.

She said in the email that, while she hopes to keep the property as a golf course, she is — as a businessperson — “evaluating all options.”

At the end of the email, she requested each member send her $9,000 in 48 hours to ensure the club reopened by Sept. 9.

No one gave her the money, McNamee states, and the course remains closed. Many club members sought more information on Jacklin.

She told club members Smith is no longer in charge, although Smith has said he is still owner of the course.

“I have asked Rich Smith to cultivate new and future business, of that which he has done,” she wrote in an August email to McNamee. “That, as someone who is about to invest millions and my time, makes sense for those who want CHNGC to improve and succeed.”

Jacklin, reached by The Daily Sun, called herself the CEO of the property, then hung up the phone when questioned further.


The residents who lent Smith a total of $2.6 million have reluctantly written off these losses, McNamee said. It is a loss to their children and grandchildren, he said, who would have inherited those investments.

At this point, McNamee said, the goal is to rescue the course and the community that surrounds it.

At a September HOA meeting, hundreds of residents were warned not to say anything disparaging about the situation of the club.

“I think the biggest loss with the closing of the course is the loss of collegiality,” resident Betty Anne Copely said.

Joelle Stanjones urged residents to keep moving forward, despite what was happening with the course and Smith.

“Let’s not let him win, and let’s be a community,” she said. “Let’s all get together and have fun like we used to. We can get through this.”

In some ways, Smith is correct in that some residents hope to get a new owner for the golf course, but not for their own profit.

McNamee spoke of a forced bankruptcy strategy at the meeting. And Dillon told residents they hoped a bankruptcy judge would allow the Bobcat Trail Community Development District to buy it at a reasonable price. The CDD would then hire a firm to run the course.

“They come in, they spend the money, they fix it up,” he said. “They get to keep the profit.”

Charlotte Harbor National Golf Course Club House

The popular club house for the Charlotte Harbor National Golf Course is closed now.

That path would prevent the helpless feeling the community has now, McNamee said. If someone else owns the course, the community has no control.

“By having ownership, we get to say, ‘You’re fired,’” McNamee told The Daily Sun.

That strategy is in limbo since Smith got the county taxes paid, McNamee said.

“We’re frustrated,” McNamee said. “It seems like he’s a cat, and he’s on his eighth life.”


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