TAMPA — Darryl Shaw first ventured into Ybor City real estate in 1988, just after he finished a bachelor's degree in international business at Brown University.
It didn't end well.
The 22-year-old moved to Ybor and bought a run-down building on E Seventh Avenue with plans to convert it to office space. Then the balcony collapsed during renovation. The city condemned the building, which had to be demolished. End of that career.
Now Shaw, 50, is back in Ybor City, and in a much bigger way. After getting an MBA and working with his brother Neil to build BluePearl Veterinary Services into a national chain of emergency and specialty animal hospitals, Shaw has purchased scores of parcels throughout the historic district over the last three years.
Working through at least 10 different limited liability companies, or LLCs, Shaw and a handful of partners have spent more than $60 million buying land in and around Ybor City. They've bought vacant lots, but also offices, small stores and restaurants, warehouses, industrial properties, a historic inn, an old cigar factory, bars, a closed spa, and church-owned land. The parcels span the historic Latin district, from Nuccio Parkway to the Crosstown Connector.
The growing empire has given Shaw and a handful of business partners an outsized stake in the fate of one of Tampa's oldest neighborhoods, one experiencing a revitalization that includes a rush of new residents, a booming small business and arts scene and, some hope, a potential home for a new Tampa Bay Rays ballpark.
Shaw says his vision for Ybor City — residential with some commercial — aligns with this rapid transformation while also maintaining the character of a historic district and its strict guidelines for renovation and building.
"I fell in love with Ybor City, with its history and culture," said Shaw, who is drawn to its immigrant backstory, diversity, architecture, authenticity, proximity to downtown Tampa and access to transportation. "It's all there, and it's rare."
Still, some of Shaw's new tenants are anxious as they wait to see how he proceeds.
Candy Qachbal's chocolate store, Qachbal's Chocolatier, just moved into a Shaw property on Seventh Avenue after redevelopment in Channelside forced the store to leave its home of 11 years.
"As long as I don't get kicked out of a spot again by redevelopment, I guess I'm okay with whatever they do," she said.
Down the street, Eric Fleming owns the Ybor City Jazz House in a newly acquired Shaw property that was damaged in a fire last year at the Amphitheatre next door. He assumes the building will need renovations, but he doesn't know what it will mean for him.
"I don't know why they bought all that property," Fleming said. "My issue is my business. I've got to let things shake out for me and I will push my buttons when I need to."
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Several of Shaw's projects have already made news, including renovations that he and a partner, homebuilder Ariel Quintela, have underway of the old Oliva Cigar Factory and Don Vicente de Ybor Historic Inn.
But the full scope of his real estate activity surprises even plugged-in locals and politicians.
Since 2014, Shaw and his partners have purchased at least 110 parcels throughout the area for a total of more than $63.5 million. That accounts for about one-fifth of the parcels that have changed hands in Ybor City since 2014, according to a Tampa Bay Times analysis of Hillsborough property records.
Mayor Bob Buckhorn had heard of the purchases, but not of their extent until told by the Times.
"Good Lord," he said. "Six-zero million?"
Yes. That's more than the $59.95 million that public records show Jeff Vinik and Cascade Investment spent buying developable land around Amalie Arena after Vinik bought the Tampa Bay Lightning. (This total doesn't include the partnership's $150 million purchase of the Marriott Waterside Hotel & Marina.)
To buy land, Shaw has worked through about 10 corporate entities, many with similar names — Ybor Marti LLC, Ybor Land LLC and Ybor Patio LLC among them — that get their mail at the same post office box in Carrollwood.
Other investors involved in some of the purchases include:
• Joe Capitano Sr., the longtime head of Radiant Oil of Tampa and a veteran Ybor City developer, landlord, civic leader and philanthropist.
• Jacob "Booky" Buchman, a major property owner, landlord and the grandson of a pioneering Ybor City retailer.
• Salvatore Guagliardo, an executive at Sunny Florida Dairy, started more than 100 years ago by an Ybor City family.
While Shaw is a relative newcomer to Ybor City's real estate market, Capitano and Buchman have bought and sold there for decades, sometimes individually, sometimes together.
"I've seen Joe and Booky at Pipo's (restaurant) swapping properties on the backs of napkins," Buckhorn said. "It's really fun to watch. They're lifelong friends and business partners, and they do it the old-school kind of way, on a handshake."
Shaw said he partnered with Capitano and Buchman because of their roots in and deep knowledge of Ybor City. Capitano declined to comment and Buchman did not respond to a message.
"I've known them for quite some time," Shaw said. "They're wonderful individuals. They come from Ybor City. They grew up in Ybor City and they have a passion for Ybor City. I've got a lot of respect for both of them, their commitment to the area and their generosity."
Two other entities that have used Shaw's home address or the Carrollwood post office box for their mail have spent another $4.4 million on a string of purchases in Ybor City. They are Fox International LLC and the Broadway Bar Land Trust. Neither responded to inquiries from the Times last week.
Shaw's name does not appear on any of the deeds, incorporation registry or other paperwork associated with those two entities. Asked if they were his, he said, "No comment."
Their purchases are primarily concentrated near other Shaw holdings east of 22nd Street, a historical divider between the bustling Ybor entertainment and nightlife of Seventh Avenue and the single-family homes and warehouses near the highways. But street improvements and changes to traffic flow around 22nd have opened up eastern Ybor to redevelopment, said John Dingfelder, a real estate agent, president of the Ybor City Rotary Club and former City Council member.
"Five years ago nobody wanted to go east of 22nd," Dingfelder said. "Now all that construction is done, and the definition of Ybor is going to be all the way to 50th Street."
Sometimes it takes an outsider like Shaw or Vinik, or, for that matter, 19th-century railroad tycoon Henry B. Plant, to see the potential in a place and make a big bet to transform it, said Columbia Restaurant owner Richard Gonzmart.
Gonzmart's family suffered through Ybor's decline in the 1960s after urban renewal pulverized the historic district. Now Shaw's commitment has helped renew Gonzmart's own confidence in Ybor's future.
Gonzmart said he's partnered with Shaw on four purchases, turned down the chance to be involved in another and found himself bidding against Shaw on still others.
"He's a quiet, unassuming, humble man" who "has been real fair in what he pays," said Gonzmart, who is working to open an Italian restaurant in the old Ferlita Macaroni building on 22nd Street, is developing plans for a Sicilian market ("I change the name weekly") and talks of building an event center in Ybor City. "I'm going to be investing $15- to $20 million over the next five years because Ybor City is going to be a place to live."
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Shaw's plan now is not too different than it was 28 years ago, though on a bigger scale. Much of what he has bought is vacant land. He intends to develop or redevelop it, largely with residential projects, done singly or a few at a time, over the next 20 years or so.
"There's not a grand master plan," he said, speaking with a barely noticeable South African accent (his family moved to Tampa when he was 8). Ybor City, he said, is well-placed to grow as part of a wider trend toward urbanization that is attracting more people to live near where they work.
"I believe that Ybor City fits in very nicely with that," he said.
He also expects Ybor's continued development to be complemented by similar efforts in The Heights and on the property downtown being developed by Vinik and Cascade Investment. He expects Tampa to end up with several distinct but well-connected neighborhoods, each with its own nuances and flavor.
"Ybor is at the junction of all of that urban excitement," Dingfelder said, mentioning Seminole Heights and the Channel District as well. "From afar I've been very impressed with what he's doing. Obviously, he's a firm believer in the future of Ybor."
Shaw expects most of his projects to be residential — a mix of houses and multi-family development — with some commercial. He expects to build some projects, lease them up, allow them to get on their feet and then move on to another project.
So far, he said, a renovation of the Don Vincente de Ybor Historic Inn is close to done, as is a separate project at the former Blues Ship Cafe. An architect is making plans for an apartment complex called the Marti, with construction likely in the range of $20 million. Work on the Marti could begin near Ybor City's entrance arch on Seventh Avenue later this year or in 2018.
"I'm encouraging everyone I know who has property in Ybor to undertake a project, not to wait to a future time, hoping that we'll reach critical mass," Shaw said.
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Several of Shaw's purchases, particularly the 7.6-acre Gas Worx site, are near the Tampa Park Apartments, which has been discussed as a possible ballpark site for the Tampa Bay Rays.
Shaw said he's talked to the Rays about the Gas Worx, a former gasification plant, "but they don't believe a ballpark can fit on that site."
Buckhorn has talked up the Tampa Park Apartments site, but said other spots in or near Ybor could make sense, too.
"Somewhere, and I don't know where the somewhere is, between Ybor and downtown, I think is the best location, and my sense is the Rays are looking at that fairly strongly," he said.
Still, even if someone tried to combine the Tampa Park Apartments property with the Gas Worx and other properties to get a big-enough site for baseball, local officials say it would be a hard sell politically.
In addition to the apartments, which are home to many families who receive subsidized housing, there are three churches nearby, plus Booker T. Washington Elementary School, plus the new Robert W. Saunders Sr. Public Library, which Buckhorn said "is not going anywhere."
"The whole issue of racial politics would be far more significant in that particular piece than it would be elsewhere, where you're dealing with just industrial buildings and willing sellers," Buckhorn said.
And the Rays seem to be aware of that, Hillsborough County Commissioner Ken Hagan said.
"They are extremely socially conscious and understand the challenges associated with the Tampa Park location," Hagan said.
Shaw said he would be happy to see the Rays come to Ybor City, but that had nothing to do with why he bought the Gas Worx.
He said he likes its size and location just outside the historic district's boundary. It's possible to build a taller building there than inside the district, where architectural guidelines limit the height of buildings. And someday it could link downtown to Ybor City.
"I fully believe the two will sort of grow together," he said.
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In his latest career as an Ybor real estate investor, Shaw has circled back to the start of his first career. After it was condemned, Shaw sold his first ill-fated property on E Seventh Avenue for $52,403.
Last year, he bought it back again for $365,300.
Times senior news researcher John Martin contributed.