Bears Dillon Thieneman’s Move to Chicago Is a Financial Win

Before Dillon Thieneman, the No. 25 overall pick in the 2026 NFL Draft, plays a single snap for the Chicago Bears, he has the option of one of the smartest financial moves in the entire first round:

He’s leaving Oregon’s 9.9% income tax for Illinois’ 4.95%. That’s a ~$500,000+ swing on the rookies signing bonus alone.

The former Oregon Duck enters the league with a ~$19.51 million rookie contract and a ~$10.5 million signing bonus.

APSM breaks down Thieneman’s real estate and residency options across his new NFL financial landscape, to suggest where the rookie could establish his primary residence to maximize his net worth and set himself up for generational wealth.

Thieneman’s NFL financial landscape:

His home state (Indiana)
His college state (Oregon)
His drafted state (Illinois)

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Does Dillon Thieneman
Own Any Property?

Thieneman was born and raised in Westfield, Indiana, part of the Indianapolis metro area, before transferring to Oregon for his collegiate career.

There are no public records of Thieneman owning real estate in Indiana, Oregon, or Illinois.

Like most NIL‑era athletes, he likely:

Rented during his days in college
Banked NIL earnings modestly and saved or used it for training and finding an NFL agent
Waiting until after the draft to make his first major real estate move

Now, with a $10.5 million signing bonus on the way, his first real estate decision is about locking in residency and maximizing compound interest.

Market #1: Indiana (Home State)

Pros

Affordable housing
Familiar environment
Strong appreciation in Indy suburbs
Low cost of living

Cons

2.95% income tax and more expensive cost of living in the Chicago region of Illinoi.
Not as tax‑efficient as Illinois for his current setup

Indiana is great for family and long‑term real estate, but not ideal as a tax home when Illinois offers a better blend of proximity and lower rate.

Market #2: Oregon (The Tax Trap)

Pros

Scenic markets and long‑term appreciation
Strong rental demand in Portland metro

Cons

9.9% income tax, one of the highest in the country
High cost of living
No financial justification for residency

Oregon is fine to rent, terrible to claim residency.
Thieneman should never establish Oregon residency if he has other options (he does).

Market #3: Illinois (Drafted State)

Pros

4.95% income tax, half of Oregon’s rate
Strong rental demand in Chicago metro
Predictable appreciation
Affordable compared to coastal NFL markets
Central location for Midwest investments

Cons

High property taxes
Slower appreciation than Sun Belt markets

Illinois is a clear financial improvement for Thieneman. He should establish Illinois residency and take advantage of the Midwest’s stability.

Best Housing Markets, Rental Markets & Appreciation Rates

Indiana

Best Housing Markets: Carmel, Westfield, Fishers, northern Indiana suburbs (relocation)
Best Rental Markets: Indianapolis metro
Appreciation: 3-5% annually

Oregon

Best Housing Markets: Portland, Bend, Eugene
Best Rental Markets: Portland metro area
Appreciation: 3-5% annually

Illinois

Best Housing Markets: Naperville, Schaumburg, Lincoln Park, Lakeview
Best Rental Markets: Chicago metro
Appreciation: 3-5% annually

Property Tax & Capital Gains Considerations

Property Tax

Indiana: ~0.85%
Oregon: ~0.9%
Illinois: ~2.1%

Capital Gains

Indiana: 3.15%
Oregon: 9.9%
Illinois: 4.95%

Illinois wins again, lower income tax, moderate capital gains, strong housing and rental demand compared to Oregon and Indiana.

Residency Impact on
Thieneman’s Signing Bonus

Gross Signing Bonus: $10,500,000
Federal Tax (37%): $6,615,000

Illinois could potentially save Thieneman:

~$520K vs Oregon
~$190K vs Indiana

That’s a half‑million‑dollar residency improvement.

Investment Scenario: Turning ~$5.98M Into Generational Wealth

Using the Illinois residency scenario:

If Thieneman invests his entire net signing bonus and lives below his means, he can turn ~$6 million into ~$9+ million before touching a dollar.

That’s how you go from “rookie contract” to multi‑generational wealth.

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APSM Real Estate Verdict

Illinois should be his primary residence.
Indiana should be his secondary or family market.
Oregon should be avoided for residency.

If Dillon Thieneman wants to maximize his rookie earnings, protect his signing bonus, and build long‑term wealth, the move is simple:

Establish Illinois residency.
Buy smart in Chicago or Naperville.
Rent in Oregon if needed.
Invest aggressively from Day 1.

Thieneman has one of the cleanest financial setups in the draft, a true Midwest tax upgrade.

Suggested Real Estate Strategy
for Dillon Thieneman

Primary residence: Illinois
Secondary: Indiana property for family or offseason base
Work base: Short‑term rental near Bears facilities
Invest: Majority of signing bonus into stocks (index funds, mutual funds), + Illinois real estate
Goal: Turn ~$6 million (net) into $9+ million by Year 5