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:
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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
Next Reads
- 2026 NFL Draft: Every 1st Round Contract Details, Net Income & Residency Analysis
- Minnesota Vikings #18 Pick Caleb Banks Should Keep His Primary Residence in Florida At All Costs: 2026 NFL Draft Real Estate & Residency Analysis
- Luther Burden III’s Fully Guaranteed NFL Rookie Contract
- Alex Bregman Signs with Chicago Cubs: Taxes, Residency & Net Income Explained
- Indiana State Athlete Taxes
Disclaimer: This article contains general financial information for educational purposes and does not constitute professional financial advice.
