From the NFL to Wooster Square

Wooster Square is the new playing field for NFL cornerback-turned-New Haven developer Kenny Hill. He’s scoring — except in one case, where he’s about to sue the city.

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Kenny Hill had to step on his tiptoes in huddles with his Oakland Raider teammates in order to see the signals. The program listed him as six-foot-one, 205 pounds; in reality, he never reached six feet or 200 pounds. You don’t find many defensive backs or linebackers that small playing for Super Bowl teams. ​“That activated me,” Hill recalls. ​“I knew I was not respected because of my size.”

Twenty-five years later, back in New Haven, the city where he made his name as a college football player, Kenny Hill has something to prove again. This time the terrain is the Wooster Square neighborhood rather than the gridiron. Instead of absorbing gut-busting body blows, Hill spends his days immersed in gut rehabs of hundred-plus-year-old homes. He’s turning neglected gems into showpiece homes — ​“and turning a profit. He hit the ground running just as a real-estate boom sent prices skyward in one of New Haven’s prime neighborhoods for young professionals and downtown workers.

Hill is working on his ninth rehab in four years of homes he’s then renting out. He’s also doing condo conversions. Along the way he has battled the perception that he’s another ​“football player with a little money who doesn’t know what he’s doing.”

Return to the Elms

Competition, big challenges, long odds, big dreams… those have been the words Kenny Hill has lived by since growing up black, one of nine children, in ​“David Duke country,” Oak Grove, Louisiana. His father ​“made it known we had to be special, we had to contribute,” and they would, unlike most of their peers, pursue higher education. Hill faced taunts when, after his all-black school burned down, he and his brother signed up to play on the all-white football team at the town’s other high school. High-school football is big in Oak Grove, so when he became the team’s star, he earned townspeople’s respect — ​“as well as the interest of college recruiters. So much interest, that he would leave his house at 5 a.m. to avoid them. He chose Yale and took his studies seriously, graduating in 1980 with a degree in molecular biophysics and biochemistry.

After college, he left for the pros. Over a ten-year career (an eternity in the NFL), he played strong safety for three Super Bowl-winning teams, the Oakland (then L.A.) Raiders in 1981 and 1984 and the New York Giants in ​’87. A subsequent career in sports marketing and consulting increasingly led him to visits to New Haven for a client.

It was then he began to notice the charms of Wooster Square, the picturesque and historic ​“Little Italy” section of town which Yale students usually discover on trips to Pepe’s and Sally’s Apizza. Hill had been one of the few undergrads not to end up there. Now he also began noticing lovely, though in some cases neglected, older homes. He saw potential — ​“and a challenge.

One day in 2000 he and a friend from Yale’s athletics department decided to buy a brick row house on Court Street for sale. Much of the rest of the block, directly across from Wooster Square’s scenic green, was in good shape. This house, like its last owner, was over 100 years old and in ill health. When the 110-year-old man who owned it died, his estate put it up for sale for $165,000. Hill grabbed it and negotiated a sale with his 80-plus-year-old daughter. People snickered at him for thinking he could make money on New Haven real estate. With savings from his football days, he had put the place redone practically from scratch, working alongside the crews, learning the process from sweeping floors and shoveling dirt to designing architectural plans and securing financing. He preserved moldings and other historic touches, but otherwise stripped it and rebuilt it. He rented it out, and he and his partner began buying other older neighborhood properties.

Meanwhile, the neighborhood was hot — ​“both the rental market, with Yale employees and office workers looking for apartments a quick walk from downtown; and the resale and condo markets. Other houses on Court Street sold for up to three times what Hill had paid for his neglected gem. Hill and his partner were able to use equity from each job to buy and rehab new ones. (They set up separate limited-liability corporations, named after Hill’s dog, for each transaction.) They have also bought properties in the East Rock and Dixwell neighborhoods, the latter of which led to a protracted fight with city government over what he calls the misuse of federal housing money. (Click here to read related story.)

With each rehab he sought to add value by finding ways to add apartments. Like the two new basement apartments he added to his latest rehab on St. John Street, a late-19th century home he bought from another elderly Italian-American longtime owner around the corner from the Wooster Square green. Hill sounds like a proud new papa as he opens the door to the basement, brimming with energy and optimism. At 47, he’s trim, in good shape, slender and slight. He still looks like no one’s idea of a pro football defenseman.

When he bought this house on St. John Street, Hill says, it was dark down there. Raw sewage covered the floors. The real-estate agents wouldn’t walk inside. Hill decided to lower the floor to make room for two separate step-down apartments. But he couldn’t fit machinery downstairs. He handed his crew shovels. He told them to dig out 30 yards of fill. The crew told him he was loco.

“Listen guys,” Hill responded. ​“Think of some of the greatest engineering feats in human history. The Sphinx. The pyramids. This is nothing.”

With the dirt cleared out, he put in hardwood floors, glass block windows, fireplaces, modern kitchens. He ended up with two spacious one-bedroom apartments fetching $1,000 each a month. On the three upstairs floors, the former two-family home now had four more new modern apartments fetching considerably more money. He put in new stairways, kitchens, heating and plumbing. On the third floor he built a back deck, complete with a garden. Looking down on the backyard next door, he noticed a trellis, and decided to put one on his new outside deck to support grapevines.

Hill is also in the midst of gutting and rehabbing a gem of a brownstone on Olive Street, again digging out a new basement apartment, restoring fireplaces, peeling off generations of paint.

Outside of his problems with the city about the house in Dixwell, Hill has gotten along fine with the city, he says. Assistant Building Inspector Mike Corbett agrees. Corbett has dealt with Hill on the Wooster Square properties. ​“I don’t really have any problems” with Hill, Corbett reports. Like other developers, Hill sometimes moves more slowly on projects that Corbett would like. But when Hill promises to fix or finish something, he does, Corbett says.

With each home, Hill battles odds, battles the inevitable unforeseen construction problems, the housing codes written long after the homes were built. He feels as though he is back competing on the ballfield.

“I walk in [to a finished rehabbed home] and say, —ÀúThis is a like a win.’ This is like having a really tough hard-fought victory against an arch-enemy in football. You walk off the field knowing you’re given everything you’ve got. You’re sore. You’re hurt. It feels so good.”