Alumnus Dan Whalen leads a $3.5 billion Cleveland development
As a star CWRU quarterback, Dan Whalen helped breathe new life into the Spartans. Now he leads a $3.5 billion development in downtown Cleveland.
Nearly 20 years ago, Dan Whalen (CWR ’10, MGT ’14) played a key role in raising the profile of Case Western Reserve University’s football program, quarterbacking the team to its first-ever NCAA playoffs and helping to attract a whole new generation of talented players.
“He was the catalyst,” said head coach Greg Debeljak.
Today, Whalen’s goal is to help reinvent a significant swath of downtown Cleveland.
As managing director for the local office of Bedrock, the real estate development company founded and chaired by Cleveland Cavaliers owner Dan Gilbert, Whalen is shepherding a $3.5 billion redevelopment project slated to replace old parking lots and industrial spaces with new residential and commercial developments, parks and performance venues, boardwalks and bike paths.
The aim, Whalen said, is to create “a livable urban core that people are drawn to not for one particular reason, but for many.”
It’s an ambitious undertaking. The master plan encompasses more than 40 acres of mixed-use developments, including a stretch of riverfront along Collision Bend, a treacherous hairpin turn in the Cuyahoga River that has caused multiple maritime fender-benders; the Rock Block, future site of Cosm, an immersive entertainment venue that will sit directly opposite Rocket Arena, home to the Cavaliers; and the cavernous mall at Tower City Center, which sits atop an active rapid transit station.
“We have some thoughts about what we’re going to do with that beast,” said Whalen, who will oversee the development of new buildings and the renovation of old ones while collaborating with the city and others to implement the necessary infrastructure upgrades.
If anyone can execute Bedrock’s redevelopment for a thriving downtown hub, it’s Whalen. By the time he came on board in February, he’d already led more than $1.5 billion in real estate development and acquisitions in Cleveland and Chicago, working on everything from apartment buildings to shopping centers and forging relationships with developers, contractors and construction firms across the region.
“He’s dreamed about things and then seen them all the way through to reality,” said Nic Barlage, CEO of Gilbert’s Rock Entertainment Group, who saw in Whalen someone who could help make Cleveland “a better place to live, work and play.”
If the past is prologue, Whalen will bring a blend of pragmatism, perseverance and creativity to the task.
A self-described “liberal arts guy” who majored in English and pursued painting and music as an undergraduate, the Greater Cleveland native (he grew up in Willoughby) also had a long-standing interest in architecture. “My favorite toys as a kid were Legos and Lincoln Logs,” he said.
“I don’t think he viewed anything as unattainable. He made a plan and he went after it. And if that didn’t work, he just pivoted and changed the plan.”—Greg Debeljak, CWRU Head Football Coach
Whalen led the Spartans to three consecutive NCAA playoffs. (He was inducted into the CWRU Athletics Hall of Fame in 2023.) And inspired by Ted Gup, a former CWRU journalism professor, Whalen initially aspired to a career as a sports journalist, interning at Sports Illustrated.
“I don’t think he viewed anything as unattainable,” Debeljak recalled. “He made a plan and he went after it. And if that didn’t work, he just pivoted and changed the plan.”
By his junior year, job prospects in journalism had dimmed due to the Great Recession. But Whalen had begun to attract the attention of pro football scouts, so he changed tack and spent two years playing in the Arena League after graduation. When that proved less than satisfying, he changed course yet again, setting his sights on a career in business and enrolling at CWRU’s Weatherhead School of Management to acquire skills he had neglected while studying Geoffrey Chaucer and William Shakespeare.
The hustle and initiative that Whalen showed on the gridiron served him well. In his first week at the Weatherhead School, he walked onto a hotel construction site and landed a job that had him helping develop hotels and residential buildings when he wasn’t in class or bartending.
After completing his MBA, Whalen moved to Chicago to help redevelop a national portfolio of shopping centers for Starwood Retail Partners, then joined Harbor Bay Ventures—a job that brought him back home to lead the development of INTRO Cleveland across from the West Side Market and one of the largest mass timber buildings in the country. He founded his own successful development firm in 2024, but the prospect of helping Bedrock rejuvenate an essential stretch of downtown Cleveland proved impossible to resist.
Work on some parts of the project, including the Cleveland Clinic Global Peak Performance Center, which will house the Cavaliers’ new practice facility, is nearly complete. Whalen expects to see more cranes in the air over the next three to five years, with “really meaningful evolution” within five to seven.
It won’t be easy. Even the topography, which features a 100-foot rise in elevation from the riverfront to Rocket Arena, poses a challenge, as does the complexity of the initiative. But none of that fazes Whalen.
Alternative career: president/general manager of an NFL franchise
Occupational hazard: the quantity of meetings and the amount of people in them.
Morning ritual: coffee, no matter what!
Hidden talent: I paint a bit, sing and play guitar.
Favorite spots on campus: Kelvin Smith Library and DiSanto Field ... obviously!
“You’re going to run into hurdles. You’re going to have issues,” he said. “And you just have to keep powering through.”
