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Bucks’ Pat Connaughton Brings Crossover Aspirations to Basketball and Real Estate

NEW YORK CITY -- When he was 17, Pat Connaughton did the unthinkable: he said “no” to the Yankees. The New York Yankees. And not just because he grew up in Arlington, Massachusetts, just outside of Boston, as a fan of the Red Sox.

“They were going to draft me [in the second round of the 2011 Major League Baseball draft], and I was going to go there straight out of high school,” he tells CloseUp360 at a Starbucks in downtown NYC during a recent road trip with the Milwaukee Bucks. “But I passed that up because of my desire to do more than just baseball.”

Despite his decision to forego the pros to pursue education, basketball and (yes) baseball at Notre Dame, Pat’s 96-mile-per-hour fastball was tantalizing enough to make him a 38th-round pick of the San Diego Padres out of St. John’s Prep (Danvers, Mass.). And though the Baltimore Orioles took him in the fourth round in 2014, after his junior year, Pat still opted to return to South Bend to get his degree from the Mendoza College of Business, before taking his talents not to the MLB, but rather to the NBA.

Nowadays, Pat, who’s in his first year with the Bucks—the top team in the NBA—after three seasons with the Portland Trail Blazers, is still a two-sport star of sorts. As he continues to pursue his hoops career, he’s also building a multi-state business in the cutthroat world of real estate development.

Pat Connaughton

Pat Connaughton is a budding star in both basketball and real estate. (Bruce Ely/Trail Blazers)

Real estate is as big in Pat’s blood as his physical capacity (and dogged work ethic) to record a 44-inch vertical leap. His father, Len, was a general contractor with a sterling reputation around Boston.

As a child, Pat remembers his dad getting picked to bid on a job remodeling a brownstone in the Back Bay that towered some five stories up.

“He could do everything they wanted,” Pat says. “His price came in lower than the other people, so in reality, you would think he would get the job.”

Instead, the project was awarded to someone else. And though Len had proved himself capable of completing the job at a high quality and with a low budget, he wasn’t going to argue—this being the house of six-time Super Bowl champion Tom Brady.

“They had a guy they wanted to go with, a guy Tom had a relationship with or one of Tom’s buddies had a relationship with,” Pat says. “So the job was probably never going to be my dad’s, but because of my dad’s reputation, they wanted to bring him in to make sure that person wasn’t screwing him.”

It was then that young Pat got a glimpse of the importance of relationships and reputation. In a business like general contracting that can lend itself to clients getting taken advantage of, being trustworthy and reliable could help someone stand out.

“It's better to miss on one or two deals in the beginning because you're trying to be sure of the deals you're doing in order to keep that reputation in a positive light, than it is just to do a deal to do a deal to try to make a quick buck,” Pat says.


By and large, though, Pat’s early education in real estate wasn’t in deal flows and finance, but rather on actual job sites. As Len and Susan’s only son, he spent his summers hauling lumber and sheetrock up and down stairs, much to his own dismay.

“[My dad] made me go through it all and it's hot as hell in the summertime back home,” Pat says, “but it taught me hard work.”

After Pat’s freshman year of high school, Len gave his son an option. He could spend his summer playing sports, so long as he met one condition.

“If you don't want to work for me all summer and you're serious about sports,” Len told him, “you're going to work out the same amount of time that you would be working for me.”

Pat held true to his word, which boded best for his prospects on the court. Though he’d long had the arm strength and competitive edge to succeed as a pitcher, he “worked a little bit harder at basketball.”

That was always a thing people always told me I could never do,” he continues. “That was always a thing, quite frankly, the 6’5” shooting guard that people are, like, ‘You don't really fit in.’ And I was, like, ‘I'm going to show you how.’”

Pat Connaughton

Pat is in his first season with the Bucks after three with the Trail Blazers. (Courtesy of Pat Connaughton)

By the time he was in eighth grade, Pat had fulfilled his sixth-grade dream by finally dunking a basketball. During the summer between his junior and senior years of high school, he exploded on the college basketball recruiting scene with an outstanding performance at a national AAU tournament in Orlando. Suddenly, Pat went from having one basketball offer at Division II Bentley University to 45 Division I scholarships at his doorstep.

“I worked hard, I worked on my body and I was able to dunk pretty effortlessly, so coupled with shooting and my decision-making and things like that, it attracted eyes,” he says. “But it was really just the fact that I had played baseball all summer every summer growing up. I never played really big-time AAU.”

Yet, as much progress as he was making towards a future in hoops, Pat still had a place in his heart for real estate.

I was always around it,” he says. “I loved it and I knew someday I wanted to get back into it.”

Pat had every reason to stick with baseball after getting drafted out of Notre Dame in 2014. During his two months of rookie ball with the Aberdeen IronBirds of the New York-Penn League, he posted an earned run average of 2.45 across six appearances (four starts). That first contract also brought with it a $428,000 signing bonus.

But rather than take the money and run from school, Pat went back to campus and used some of his earnings to dip his own toes into the real estate business. Going into his senior year at Notre Dame, Pat used some of his bonus to buy a house in South Bend to live in. During that year, Len spent time around town to help his son fix up the place before “flipping” it for a profit following Pat’s graduation.

“It gave him an excuse to watch basketball games,” Pat says.


For Pat, it opened his eyes to what he could achieve in real estate, regardless of how his athletic career turned out. He had a mind for math growing up and a long-term vision for his life that aligned with Notre Dame’s “4 for 40” (“That's four years, but it's a 40-year decision for your life,” Pat explains). But now he had tangible proof of what that could be, beyond the case studies he had conducted and presentations he had given en route to his degree in management consulting.

So when the Brooklyn Nets made him the No. 41 pick in the 2015 NBA draft, and subsequently traded his rights to the Trail Blazers, he saw the potential of what he could create even with the relatively modest contract of a second-round rookie.

Once again, Len was there to help. He dissolved his own company and helped his son start his own called Beach House LLC, with Joseph Stanton, Pat’s close friend since the age of two, serving as the director of project management.

“The name of it just kind of came from everyone wanting a beach house,” Pat says.

Despite playing in the NBA, Pat didn’t quite have the means to develop beachfront property—certainly not on his own. Instead, his company started with a handful of quick projects remodeling kitchens and bathrooms in Portland and South Bend, with Len overseeing day-to-day operations while Pat pursued pro basketball with the Blazers.

“He’s old enough now where he could probably retire, but he loves it,” Pat says of Len. “And doing it with me is even better. For me, quite frankly, it’s better than probably it is for him.”

Not that Pat left it all to his dad and his best friend. Along the way, he used the resources and network made available to him by both the NBA (including the Crossover Into Business program at Harvard Business School) and the National Basketball Players Association (like the union’s Real Estate Symposium) to further educate himself on real estate and build his contacts in the business world. Like fans waiting for autographs outside the team hotel, Pat found people in the corporate world also wanted to be in close proximity to pro athletes.

“That might get me in the door, but what’s going to keep me in the door is you understanding I’m an articulate young man that wants to learn from you, wants to be mentored,” he says. “So I found myself networking my way into plenty of different doors that I probably had no business being in.”

Pat Connaughton Joseph Stanton

Pat has been best friends with Joseph Stanton since he was two years old. (Courtesy of Pat Connaughton)

As people in the business world started to see Pat as more than an athlete, so too did his teammates and peers in the NBA. They began to wonder why this young guy, who was still getting his bearings in the league, was doing so much off the court—and making so much extra money in the process. Any skepticism therein quickly turned to curiosity and, in some cases, a desire to get involved in what Pat was doing.

If I was Giannis [Antetokounmpo] making $20-something million a year, would I take the time to bring on investors or would I just do it all myself?” he wonders. “I wouldn’t need to.”

But Pat wasn’t making anywhere near that kind of superstar scratch, and still isn’t. And given his social proclivities, he combined the relative weakness of his own pocketbook and the interest from other players into a strength.

“I value the relationships,” he says. “And so for me, I’d rather go bankrupt on my own money before I lose somebody's that's having faith in me because of the relationship I have.”

Pat says he now has “around 10” other pro athletes invested in Beach House, though he declines to reveal any of them by name. He doesn’t rely on the money from his peers to do what he does. Nor does he specify any particular threshold for them to invest.

“There’s no pressure on how much you want to put in, how little,” he says. “There's no pressure if you don’t want to put anything in and you just want to see how a project goes from start to finish.”

For Pat, it’s not about the money. Again, it comes down to relationships. With so many outsiders coming at his peers hawking business ideas and seeking chunks of their salaries in return, Pat presents himself as a clear alternative, as someone with credibility in both pro sports and real estate who doesn’t need the additional capital, but is capable of putting it to work when it comes.

“Pro athletes, it is kind of like a fraternity,” he says, “and when one of their own is able to have the same type of business acumen and be able to accomplish the same things, they would prefer to be involved with someone that can see eye-to-eye with them.”


Real estate has done and continues to do a lot for Pat. It’s provided a foundation upon which he’s strengthened already-tight bonds with his father and best friend. It’s connected him more closely to influential figures across basketball and business—including Don Peebles, the founder, chairman and CEO of the Peebles Corporation, which develops luxury hotels, and high-rise residential and commercial properties across the country. It’s set him up for success after basketball, in a field he loves.

For now, it also serves as an outlet. Where others in Pat’s position—as a lightly used role player on a stacked Bucks squad—might feel angst over a lack of playing time, he has other interests in business to keep him “sane” when basketball isn’t going his way.

“I'm still in the gym more, but I also have something when I go home where I'm not thinking, ‘Oh, I didn’t play tonight, I’m not shooting well, I’m not playing well,’” he says. “I'm thinking about other things that I can do to make myself successful away from basketball.”

That, of course, includes building out his real estate portfolio. For Pat, that doesn’t mean plunking down exorbitant sums to build towering skyscrapers, but rather filling the niche between small- and big-time developers with projects that, upon completion, will allow him to have direct relationships with investors and sometimes even tenants, depending on the project.

Through Beach House, he recently purchased a building in downtown Milwaukee that they plan to tear down and turn into luxury apartments. He’s also developing a mixed-use building with a penthouse residence he’s constructing back in South Bend, to cater towards “high-net worth” Notre Dame alumni who want a nice, quiet, private place to stay when they come to town for football weekends.

I don’t want to charge an arm and a leg for it,” Pat says. “Sure, I want to make money on it, but that relationship that I develop with them is going to hopefully extend to maybe other business opportunities, and different things just because of real estate.”

Pat Connaughton Mike Brey Notre Dame

Pat, pictured here with Notre Dame basketball coach Mike Brey (center), conducts some of his real estate business in South Bend. (Courtesy of Pat Connaughton)

To that end, Pat sees real estate as that foot in the door to the wider business world.

“I love how businesses work,” he says. “I think real estate, for me, is a thing that I’ll always do and always have, but real estate isn’t for everybody. Not everybody has that.

“So if I can be well versed in other areas of business or at least meet the people that are well versed, learn from them, things of that nature, then I’ll be able to help a lot more people. And I’ll be able to do a lot more things than just develop real estate 24/7, which I'll probably do anyway.”

Among those Pat most wants to help: his fellow athletes. Beyond having a couple handfuls invested in his real estate business, as well as dabbling in venture capital and other businesses, he wants to show his peers how they can be successful off the court by invoking the same basic principles of teamwork that help them win on it.

“I think the reputation is the biggest thing,” he says. “That’s why I want to have a reputation of a businessman because I think when you walk into the room, corporate people don’t just see me as an athlete. But then athletes don’t just see me as an athlete.”

Pat Connaughton

Pat spent time on construction sites as a kid, long before he got into making real estate deals. (Courtesy of Pat Connaughton)

For all that he’s been able to accomplish in business during his four years in the NBA, Pat is still focused on sports. Besides the hour or so he spends per day checking up on Beach House, he’s locked into Milwaukee’s championship chase, and hasn’t ruled out trying his hand at pitching again once he’s done with basketball.

“I never dreamed of being a businessman. I dreamed of being an NBA player, an MLB player,” he says. “So you could say my athletic career is probably ahead of my business career in that case.”

Pat should have ample time to bring his business acumen up to par with his athletic accomplishments over the course of his life.

Not that he’s waiting for the latter to end before he gets the former up to speed with his fastball.


Josh Martin is the Editorial Director of CloseUp360. He previously covered the NBA for Bleacher Report and USA Today Sports Media Group, and has written for Yahoo! Sports and Complex. He is also the co-host of the Hollywood Hoops podcast. Follow him on Twitter and Instagram.

Additional reporting by Mike Mazzeo.

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