Wait… What?… One Of Hillsdale College’s Trustees Was An Obama-Biden Elector?

How A Family Tied To Clinton-Era Democratic Politics Helped Slide A Massive California Property Into “Conservative” Hillsdale’s Hands 

Hillsdale College Built Its Reputation By Standing Apart From The Political Establishment. So How Did One Of California’s Most Politically Connected Democratic Families Help Put A Nearly $100 Million Property In Hillsdale’s Hands — And Then Wind Up Inside The College’s Boardroom? 

I have a little dog in this hunt.

Here’s the story:

My daughter went to Hillsdale College as a basketball recruit, and I spent enough time around the place that I occasionally found myself sitting next to Hillsdale president Larry Arnn at a basketball game or two. Naturally, I discussed a few things with him other than whether we should play man-to-man or zone defense.

Good discussions, too. Charitable. Fun. The kind where two grown men can disagree without declaring the other fellow a communist, fascist, heretic, or threat to Western civilization before halftime.

So understand something before we open this gate: I’m not writing as somebody who hates Hillsdale College.

Quite the opposite. I love it there!

Like thousands of conservative parents, I knew what Hillsdale represented when we sent our daughter there. (She was recruited by Michigan State, the Naval Academy, and a bunch of other big-name D1 schools) Hillsdale has built a great national reputation around classical education, constitutional government, Christianity, opposition to Progressivism, and independence from government money.

In fact, in its own announcement of this California project I’m about to discuss, Hillsdale described itself as having a “principled refusal to accept federal or state taxpayer subsidies.” That’s part of the Hillsdale brand, and it’s one reason conservative parents and donors trust the place.

Fair enough.

But here’s another old-fashioned principle worth remembering: If you’re going to hang a big sign on the barn telling everybody what’s inside, you shouldn’t be offended when somebody opens the door and looks around.

And recently, thanks to Brad Birzer, Hillsdale professor… what I found behind Hillsdale’s California barn door is fascinating.

Start With 1,100 Acres

In 2021, Hillsdale announced an extraordinary California gift.

The University Development Foundation, or UDF, transferred roughly 1,100 acres in Placer County, California, to Hillsdale for a future educational operation. Hillsdale’s own announcement credits Sacramento developer Angelo K. Tsakopoulos with leading the group that originally donated the land to UDF in 2012, and the college also identifies William and Claudia Cummings and the Wayne Prim family among the original benefactors.

Sounds simple enough. Some wealthy people had land, they wanted higher education in the region, and eventually Hillsdale got the property.

Put a bow on it and send everybody a Christmas card.

Except the financial records tell us this wasn’t exactly the back forty behind Grandpa’s farmhouse.

UDF’s IRS records show that at the end of 2019 the foundation held approximately $100.4 million in assets, against about $7.5 million in liabilities, leaving nearly $92.94 million in net assets. The foundation’s assets were therefore overwhelmingly tied up in something much more substantial than an ordinary annual charitable operation.

Then came the Hillsdale transaction.

UDF’s later filings show its assets essentially disappearing through charitable distributions as the property moved into Hillsdale’s orbit. Hillsdale itself says the gift wasn’t merely land for classrooms: a portion would become an educational center, while the remainder would be developed and sold, with the net proceeds dedicated to Hillsdale College.

In other words, somebody didn’t just pass the collection plate.

They practically passed the farm.

Except This “Farm” Came With A Development Plan

This is where the story gets more interesting.

The California property wasn’t conceived merely as 1,100 acres where somebody might someday build classrooms, dormitories and a football field. It was part of a much larger university-centered development involving housing, commercial development, roads and other infrastructure.

And the development side wasn’t some decorative windmill sitting beside the barn.

It was part of the financing strategy.

Long before Hillsdale entered the picture, the University Development Foundation told Placer County that development and sale of the community portion could be used to help fund the university endowment. The common-sense logic isn’t difficult to understand: a prospective university would rather see money already sitting in the bank than hear somebody promise that the money might appear after enough houses were eventually sold.

So the basic machinery looked something like this: obtain the entitlements, develop portions of the property, sell portions of the property, and use those proceeds to help support the educational institution.

There’s nothing inherently sinister about that I guess.

But let’s call the cow a cow.

This wasn’t merely a land donation. It was a land-development engine attached to a university project.

And Hillsdale eventually became the university.

Now Meet The Tsakopoulos Family

Here’s where the political wiring starts looking like somebody crossed the red and black cables.

Angelo Tsakopoulos isn’t merely a businessman who once sent $50 to a Democratic candidate because his neighbor asked nicely. Contemporary reporting describes decades of substantial involvement with Democratic candidates, fundraising and politics.

And the trail runs straight through Bill and Hillary Clinton.

In 2008, the Los Angeles Times reported that for “the better part of two decades,” Bill and Hillary Clinton had counted on the support and money of the Tsakopoulos family. Angelo was described as one of Bill Clinton’s early California supporters, while his daughter Eleni Tsakopoulos Kounalakis was one of Hillary Clinton’s active fundraisers.

Another Los Angeles Times report described Angelo and Eleni as “Hillary people all the way.” Eleni explained that her father had hosted President Bill Clinton at his home and said Democratic politicians regularly sought the family’s support.

But this relationship went considerably farther than yard signs and rubber-chicken fundraising dinners.

During the Clinton administration, Angelo and Sofia Tsakopoulos were among the Californians who stayed overnight at the White House during the period when the Clinton administration faced intense scrutiny over access given to major political supporters. Clinton denied that the Lincoln Bedroom was ever “sold,” and nothing I’ve found establishes that the Tsakopouloses purchased an overnight stay.

That’s an important distinction.

But the surrounding facts are remarkable enough without embellishment.

A separate 1997 Los Angeles Times investigation described Angelo as a longtime Democratic fundraiser, reporting that he’d donated $165,000 to the Democratic National Committee the previous year. The paper reported that he attended a White House state dinner, participated in a White House coffee with President Clinton and stayed overnight in the Lincoln Bedroom.

The same investigation reported something particularly relevant to the real-estate side of our story. At the time, Tsakopoulos was fighting federal regulators over development and environmental issues involving California property, and the Times examined whether his political access helped him obtain favorable treatment. Tsakopoulos denied using his political influence for personal business benefit, while Clinton administration officials denied trading government action for political contributions.

Those qualifications matter.

But so does the underlying picture.

This family wasn’t standing on the edge of Democratic politics waving through the fence.

They were well inside the pasture.

Then Came Hillary… And Obama

The relationship continued into the next generation.

When Hillary Clinton and Barack Obama fought for the 2008 Democratic presidential nomination, Angelo and Eleni supported Hillary. Kyriakos Tsakopoulos — Angelo’s son — broke with them and backed Obama instead.

And this wasn’t a quiet vote behind a curtain.

The Los Angeles Times reported that Kyriakos planned to fly to Chicago to meet with Obama’s campaign about how he could help and was offering to raise money for Obama. The newspaper also reported that the Tsakopoulos family had donated and raised millions of dollars for Democrats in California and nationally.

Angelo’s daughter Eleni eventually became even more prominent politically. She was a major Democratic fundraiser before President Obama appointed her U.S. ambassador to Hungary, and she later became California’s lieutenant governor; during that race, the Los Angeles Times reported that Angelo contributed $5 million to an independent expenditure supporting her campaign.

Another Times profile subsequently described Angelo as having donated tens of millions of dollars to Democratic candidates, including his daughter, and specifically traced the family’s political connections to Bill and Hillary Clinton.

Again, none of this makes these people bad.

That’s not the point.

The point is that describing the Tsakopoulos family merely as “philanthropists” leaves quite a few fence posts out of the story.

Now Follow That Trail Back To Hillsdale

Kyriakos Tsakopoulos eventually became deeply involved with the University Development Foundation, the organization controlling this enormous California university project.

And UDF spent years trying to bring a university to the property. Hillsdale wasn’t the original intended beneficiary, which is an important part of the story because it prevents us from pretending that Angelo Tsakopoulos woke up one morning and decided to hand Hillsdale College $100 million.

That’s not what happened.

What happened is more interesting.

After earlier university plans failed, Hillsdale entered the picture. Eventually the relationship produced the transfer of the 1,100-acre property, and Hillsdale openly thanked the people responsible.

Larry Arnn said:

“We are honored by it and grateful for it.”

Hillsdale’s own announcement praised Angelo Tsakopoulos and the other benefactors. Angelo, in turn, praised liberal arts education and specifically talked about teaching America’s founding principles and the Constitution.

Pause over that for a moment.

A man with decades of involvement in Democratic politics, ties to Bill and Hillary Clinton and extensive real-estate interests helped create the property. His son backed Barack Obama and became centrally involved in the foundation controlling it.

And the ultimate beneficiary became…

Hillsdale College.

If you wrote that into a novel, your editor might send it back for being too cute.

Then The Relationship Moved Into Hillsdale’s Boardroom

You might assume the relationship ended after the land changed hands.

It didn’t.

In May 2025, Hillsdale elected Kyriakos Tsakopoulos to its Board of Trustees. Hillsdale’s official announcement describes him as co-chairman of AKT Investments Inc., the family’s Sacramento real-estate investment company, and explicitly says that he “assisted Hillsdale College with its plans to locate in California.”

Hillsdale didn’t bury this information. Quite the opposite: its announcement praised Tsakopoulos as someone who would help continue the college’s tradition of “sound learning,” “high moral character,” the Christian faith and freedom.

That’s worth thinking about.

A politically connected California family helps create an enormous university-development project. The project eventually lands with Hillsdale, and a member of that family ultimately lands on Hillsdale’s governing board.

This isn’t looking much like a one-night date anymore. It’s a relationship.

Now Here’s Where Common Sense Has To Take Over

The cheap version of this story would scream:

HILLSDALE TAKES $100 MILLION FROM DEMOCRATS!

That’ll get clicks. It’ll also leave half the truth lying dead beside the road.

The property wasn’t originally donated specifically to Hillsdale. The project was intended to attract a university to the Sacramento region, and Hillsdale eventually became that institution after earlier plans didn’t work out.

Political disagreement doesn’t make someone’s charitable contribution dirty money, either. There’s actually something encouraging about people who disagree politically cooperating around education.

I’ve argued with Larry Arnn myself.

I didn’t expect him to throw me out of the gym, and he didn’t.

That’s civilization.

But there’s another kind of common sense too.

You don’t spend all summer warning your neighbors about foxes and then act surprised when they ask about the fox sitting on your porch.

Hillsdale has become enormously influential among conservative Americans partly because people believe it stands apart from America’s political and educational establishment. Its publications, courses and speakers regularly examine Progressivism, constitutional government, centralized power and the modern administrative state.

That’s perfectly legitimate.

But it makes this relationship worth understanding.

Not because Democrats have cooties.

Because institutions should be judged by the same standards they encourage the rest of us to apply.

Maybe The Real Lesson Is More Complicated

Perhaps Hillsdale makes a clear distinction between Democratic politicians, Democratic voters and Progressive political philosophy.

If that’s the explanation, there’s nothing unreasonable about it. In fact, I hope that’s the explanation, because America desperately needs institutions where disagreement doesn’t automatically require excommunication.

Maybe Angelo Tsakopoulos can admire Bill Clinton and still admire the Constitution. Maybe Kyriakos can support Barack Obama and still believe Hillsdale teaches something valuable, and maybe Larry Arnn can disagree profoundly with their politics while happily sitting down at the same table.

Lord knows we could use more of that.

But then Hillsdale should be careful about letting political rhetoric collapse those distinctions elsewhere. Once an institution has welcomed into its governing structure people with significant connections across America’s political establishment, it has demonstrated something rather important.

The world is considerably more complicated than “our side good, their side bad.”

And Then There’s The Government Question

There’s another wrinkle here that deserves careful wording.

Hillsdale proudly says it doesn’t accept federal or state taxpayer subsidies. Nothing I’ve uncovered changes that basic claim or establishes that Hillsdale accepted those kinds of subsidies through this California project.

But the California development does interact with local government in ways ordinary real-estate projects do.

A 2022 Hillsdale/UDF letter to Placer County explains that the county had allowed UDF to delay payment of certain county staff costs associated with permits and entitlements. When UDF transferred the property to Hillsdale-controlled HC Real Estate Holdings, that transfer triggered payment obligations, so agreements were amended to delay payment until a later stage in the residential-development process.

That’s not the same thing as receiving taxpayer funding.

Let’s not pretend it is.

But it does demonstrate how much more complicated a 1,100-acre development becomes once you leave the brochure and start reading the agreements.

And I Still Want To Follow The Land

Because underneath the political story sits another story that may ultimately be even bigger.

Real estate.

Remember, this wasn’t merely a university parcel. Hillsdale itself says the unused portion of the property will be developed and sold, with net proceeds going to the college.

And the Tsakopoulos family didn’t make its fortune selling homemade jam at the farmers market.

They made it in California real estate development.

A 2006 Los Angeles Times investigation reported that Angelo controlled approximately 40,000 acres of Central Valley land and examined the intersection of his extensive development interests, lobbying and political relationships. The paper reported that Tsakopoulos and his family had already put millions into state and federal politics by that time.

Again, that doesn’t prove anything improper happened with Hillsdale.

But any old farmer understands what happens when somebody announces they’re building roads, houses, stores and a nationally known college next to your field.

Yesterday you owned dirt.

Tomorrow you may own development property.

So there are still some mighty interesting questions standing out there by the fence. Who were all the original partners behind the land? What property did they contribute, and what property did they keep? Who owns the surrounding acreage today, and how did the zoning and development entitlements change?

Then come the money questions. Who builds the houses? Who develops the commercial property? How much money will ultimately flow to Hillsdale? And did nearby land owned by any original participants increase in value because the university-centered development became viable?

Those questions aren’t accusations.

They’re due diligence.

Because Sunshine Isn’t An Attack

That’s the distinction I want to make especially clear.

Hillsdale College doesn’t become a bad institution because people associated with Democratic politics helped it. Angelo Tsakopoulos doesn’t become a bad man because he supported the Clintons, and Kyriakos doesn’t become a bad trustee because his political history differs from what many Hillsdale supporters might expect.

Larry Arnn isn’t required to agree politically with everybody whose generosity helps Hillsdale, either.

But when a college has built a substantial national following around independence, constitutionalism and opposition to Progressivism, its supporters deserve to understand who’s helping finance major projects and how those relationships work.

Especially when we’re talking about an asset whose reported value approached $100 million and a real-estate development designed, at least in part, to turn land into money for the educational institution.

That’s not gossip.

That’s journalism.

And maybe there’s a lesson here that reaches considerably farther than Hillsdale College.

We conservatives spend plenty of time studying Washington’s institutions, following the money and warning ordinary Americans not to accept whatever label somebody slapped on the package. Good. We should.

But principles aren’t principles if they only work when we’re examining somebody else’s barn.

Sometimes you have to walk behind your own.

Sometimes you have to read the deed, pull the tax filings and follow the money. And sometimes the tracks lead somewhere you weren’t expecting.

In this case, they lead from California real estate to decades of Democratic fundraising… from Bill and Hillary Clinton to Barack Obama… and eventually through the gates of Hillsdale College itself.

That’s an unusual trail.

And if Grandpa taught us anything about figuring out what happened on the farm, it was this:

When the story you’re being told doesn’t quite explain all the tracks in the mud, don’t immediately accuse anybody of stealing the tractor.

Just keep following the tracks.