NUA Strategy for Insurance Company Employees (Progressive, Hartford, Allstate, Travelers, Chubb)

Property and casualty insurance employees are rarely the first group that comes to mind for NUA planning — but they should be. Long-tenure claims directors, underwriting managers, and actuaries at Progressive, The Hartford, Allstate, and Travelers have accumulated employer stock over 20–30-year careers, and the 2008–2012 financial crisis compressed cost bases to a fraction of today's prices for anyone who kept contributing through those years. Progressive employees who averaged into PGR stock from 2009–2014 at $17–$30/share hold positions now worth over $213/share — ratios of 7:1 to 12:1 on those specific lots. Hartford employees face an even more dramatic story: HIG fell to $3.33 in March 2009 before recovering to over $130 today. There is one important caveat that a generalist advisor will miss if they do the NUA math without asking: nearly every major P&C insurance company is headquartered in a state — Connecticut, New Jersey, Illinois, or Ohio — that taxes long-term capital gains at the same rate as ordinary income. The NUA advantage for most insurance company employees is federal-only. That still saves $50,000–$150,000 or more in lifetime federal tax for 37%-bracket employees with significant appreciation. Here is the full carrier-by-carrier breakdown.

Why P&C insurance employees are NUA candidates

Three structural features of long-tenure P&C insurance careers produce favorable NUA conditions:

• Long average tenure. Claims adjusters, actuaries, underwriters, and operations managers at major P&C carriers routinely spend 20–30 years at a single company. Employer match contributions in company stock, compounding across that timeline, create positions that look nothing like the original purchase price — particularly for employees who contributed through the 2008–2012 distressed period.
• Financial crisis price compression. Unlike the 2000–2002 dot-com collapse (which hit tech but left many P&C insurers relatively intact), the 2008–2009 financial crisis hammered the insurance sector because of investment-portfolio losses, AIG contagion, and market-wide panic. Hartford Financial fell 97% from its 2007 peak to its March 2009 low of $3.33.¹ Allstate fell from $65+ in 2007 to below $18 in early 2009. Employees who maintained 401(k) contributions and employer match allocations in company stock through that trough period now hold shares at dramatically low per-share cost bases.
• ESOP structures at Hartford and Allstate. Both The Hartford and Allstate operate formal Employee Stock Ownership Plans (ESOPs) integrated into their 401(k) structures, meaning a portion of employer contributions is channeled specifically into company stock — not as an employee's investment election, but as a plan-level employer contribution. This can produce larger-than-expected employer stock balances even for employees who never actively chose to hold company stock.

Carrier summary table

Progressive Corporation (PGR)

Progressive's 401(k) plan — The Progressive 401(k) Plan — covers approximately 47,000 employees and uses Fidelity NetBenefits as the recordkeeper.⁴ The plan allows employees to invest in PGR common stock directly through the plan's investment menu, and employer match contributions are made in cash that employees can direct into PGR stock.

The NUA opportunity at Progressive is driven by the company's extraordinary long-term stock performance. PGR traded at approximately $17–$18/share in 2009, and as of September 2026, trades around $213/share — an appreciation of more than 12× from that trough. But Progressive is unusual among P&C insurers: unlike Hartford and Allstate, which faced near-collapse in the financial crisis, Progressive remained financially stable throughout 2008–2009 (its business model of short-duration auto and homeowners policies creates far less investment-portfolio sensitivity than life or financial-guarantee insurers). The company's appreciation reflects decades of operational excellence and market share growth, not just a crisis-recovery bounce.

The appreciation trajectory:

• 2009: ~$17–$18/share
• 2012: ~$19–$22/share
• 2015: ~$29–$34/share
• 2020: ~$95–$110/share
• September 2026: ~$213/share

An employee who averaged into PGR stock from 2009–2015 at roughly $22/share now holds shares at 9.7× that basis. The critical point: recent contributions from 2021–2026 at $95–$220/share have a blended basis that dramatically dilutes the overall ratio. This is why partial NUA lot selection matters here — if the employee can identify and NUA only the 2009–2016 vintage lots, the savings are far larger than NUA-ing the whole position at the blended basis.

Ohio state tax note: Progressive is headquartered in Mayfield Village, Ohio. Ohio taxes long-term capital gains as ordinary income (same rate schedule), so Ohio-based Progressive employees receive federal-only NUA benefit. The 2026 Ohio rate is 2.75% on income from $26,051–$100,000 and 3.5% on income above $100,000. This is not insignificant — but unlike high-rate states like California or New York, the Ohio state tax drag on a moderate-sized NUA position is limited. The federal savings remain very large regardless.

The Hartford Financial Services (HIG)

The Hartford's 401(k) plan — the Hartford Investment and Savings Plan — uses Fidelity Workplace Services LLC as the plan's recordkeeper, confirmed by the plan's 2025 Form 11-K SEC filing.¹ The plan includes an Employee Stock Ownership Plan (ESOP) component effective November 29, 2001, meaning a portion of employer match contributions specifically channels into Hartford Financial common stock (HIG) rather than a general investment account. Participants who joined before or during the financial crisis may have accumulated significant ESOP-sourced HIG shares at dramatically compressed basis prices.

The Hartford's crisis-era basis story is exceptional: HIG reached an all-time closing low of $3.33 on March 6, 2009,⁵ a 97% decline from its pre-crisis peak, as the market feared Hartford was on the path of AIG. The company ultimately survived — it sold its life insurance operations in 2013 and refocused on P&C — and HIG stock recovered steadily. As of 2026, HIG trades around $130/share (52-week range approximately $105–$145), representing a 15-year total return of approximately 698%.⁵

What this means for NUA:

• Employees who contributed to the ESOP/401(k) during 2009–2012 at basis prices of $10–$28/share (averaging through the year, not just the panic-bottom) now hold shares at $130 — ratios of 4.6:1 to 13:1 on those specific lots.
• Employees who contributed before the crisis (2001–2007) at $50–$100+/share have modest ratios of 1.3:1 to 2.6:1 on those lots — below NUA's typical breakeven for high-bracket filers.
• The divergence between pre-crisis and crisis-era lots makes Hartford a classic partial-NUA case: NUA the low-basis crisis-era ESOP shares; roll the higher-basis early lots to the IRA.

Connecticut state tax note: The Hartford is headquartered in Hartford, Connecticut. Connecticut taxes long-term capital gains at the same graduated rate as ordinary income — up to 6.99% for income above $500,000 (single) or $1,000,000 (MFJ) for 2026. Hartford Financial employees receive federal-only NUA benefit. For a 37%-bracket employee with a $500,000 NUA position, CT taxes are the same whether the shares are distributed via NUA or eventually rolled out of an IRA as ordinary income. The federal savings is not reduced — it remains the spread between the federal LTCG rate (20% + 3.8% NIIT) and the federal ordinary income rate (37%).

Allstate Corporation (ALL)

Allstate's 401(k) plan — the Allstate 401(k) Savings Plan — incorporates both a leveraged and a nonleveraged Employee Stock Ownership Plan (ESOP) component specifically designed to invest in Allstate Corporation common stock (ALL).² This means Allstate employees have an ESOP-sourced employer stock position that accumulates separately from their own 401(k) investment elections. Plan service provider documentation confirms Voya Retirement & Annuity as the plan trustee and service provider; participants should verify the current recordkeeper through the Allstate Benefits Center at (888) 255-7772 or their current benefits portal, as recordkeepers can change during plan transitions.

Allstate's stock price was severely compressed during the financial crisis:

• Pre-crisis peak (2007): ~$65+/share
• Crisis trough (2009): ~$16–$18/share
• 2012: ~$30–$33/share
• 2015: ~$60–$70/share
• 2020: ~$95–$115/share
• September 2026: ~$250/share

An Allstate employee whose 401(k)/ESOP contributions averaged $25/share during 2009–2013 now holds shares worth ~10× that cost basis. The ESOP structure means these shares were contributed by the employer — not by the employee's own investment election — so the participant may have a substantial ALL balance without actively choosing to hold company stock.

Allstate also completed the sale of its life and annuity businesses to Blackstone in January 2022 and has been focused on P&C since. Long-tenure employees (20+ years) whose contributions spanned the pre-spinoff and post-spinoff era need to confirm which plan holds what assets — the P&C-focused 401(k)/ESOP is the one relevant to NUA.

Illinois state tax note: Allstate is headquartered in Northbrook, Illinois. Illinois has a flat income tax rate of 4.95% that applies equally to ordinary income and long-term capital gains. Like Ohio, the NUA benefit for Illinois-based Allstate employees is federal-only. There is no state LTCG spread in Illinois. The state tax paid on the NUA position (4.95% of the full market value) is the same whether it is distributed as NUA or eventually distributed from an IRA as ordinary income.

Travelers Companies (TRV)

Travelers Companies — headquartered in Hartford, CT and New York, NY — is one of the largest property casualty insurers in the United States. Its 401(k) savings plan covers a large workforce of underwriters, actuaries, claims managers, and operations staff. The plan uses Fidelity as the recordkeeper (verify through your current benefits portal, as plan administration details can change).³

Unlike Hartford Financial, Travelers entered the financial crisis in far stronger financial condition (no material AIG-style investment-portfolio exposure, no near-collapse) — which means its stock did not experience the same catastrophic low. Nevertheless, TRV was not immune:

• 2009: ~$30–$45/share (ranged widely as markets recovered through the year)
• 2012: ~$60–$70/share
• 2015: ~$100–$115/share
• 2020: ~$100–$130/share (COVID compression then recovery)
• September 2026: ~$375/share (all-time high of ~$396 reached July 2026)

For an employee who averaged into TRV stock from 2009–2014 at approximately $55/share, the current $375 price represents a 6.8:1 ratio — well above the NUA breakeven for 37%-bracket employees. For contributions from the full career (2000–2026 average, blending pre-crisis $40–$60 lots with post-crisis $100–$300 lots), the blended ratio is typically 3:1 to 5:1 depending on contribution timing.

Travelers also has significant operations outside Connecticut — including claims offices, underwriting centers, and service centers in Texas, Florida, Georgia, and other no-LTCG-parity states. Travelers employees based in those states capture the full federal + state NUA advantage (see state table below).

Chubb Limited (CB): the ACE merger context

The company currently trading as Chubb Limited (CB) is the result of ACE Limited's acquisition of the original Chubb Corporation in January 2016. ACE paid approximately $28.3 billion for Chubb, with original Chubb shareholders receiving 0.6019 ACE shares plus $62.93 in cash per Chubb share. ACE then renamed itself Chubb.

This merger creates two distinct employee populations to analyze:

1. Former ACE employees: ACE stock in 2009–2013 averaged roughly $55–$90/share, and the current CB price of ~$348 represents a 3.9:1 to 6.3:1 ratio on those lots. Employees who contributed heavily during that period have meaningful NUA opportunities.
2. Former original-Chubb employees: Original Chubb stock converted to ACE/CB shares at the 0.6019 exchange ratio at merger in January 2016. CB at merger was priced around $105/share at the time. At $348 today, that represents a 3.3:1 ratio from the merger value — decent but not exceptional compared to crisis-era contributions at pre-2010 ACE prices.

The key practical step for former original-Chubb employees: confirm whether their plan records the cost basis as the original Chubb share purchase price (adjusted for the exchange ratio) or as the ACE share price at the merger date. The correct answer is the former — basis carries through tax-free reorganizations — but recordkeeper systems sometimes use the merger-date market price as a shortcut, which overstates basis and understates the NUA amount. Verify this before modeling the election.

Chubb Limited is domiciled in Zurich, Switzerland with U.S. operations headquartered in New Jersey. New Jersey taxes long-term capital gains as ordinary income at rates up to 10.75% — among the highest state LTCG burdens in the country. Chubb employees in New Jersey receive federal-only NUA benefit, but the federal savings is still very large for senior employees in the 37% bracket.

Life and group insurance: modest ratios, different dynamics

Several major life and group insurance companies are worth brief mention — not as high-conviction NUA cases but as situations that require verification:

• MetLife (MET): MetLife demutualized in April 2000, converting to a publicly traded company. MET stock has traded in the $30–$75 range over the past decade. Employees whose cost basis dates from post-demutualization contributions in the $30–$50 range face a 1.5:1 to 2.5:1 ratio at current prices — typically below the NUA breakeven for 37%-bracket filers. NJ headquarters means federal-only benefit even if ratios improve.
• Prudential Financial (PRU): Prudential Financial demutualized in December 2001. PRU has traded from approximately $55 in 2012 to ~$120 today — a 2.2:1 ratio on 2012 contributions. NJ headquarters. Federal-only benefit, and ratios are typically at or below breakeven for high-bracket employees.
• Lincoln National (LNC): Lincoln National fell dramatically in the financial crisis (LNC fell from ~$70 in 2007 to below $7 in March 2009) and has recovered — but not as dramatically as the P&C carriers. Current LNC is below $35/share; 2009-era contributions at $5–$15 would represent 2:1 to 7:1 ratios. However, Lincoln also has a large 403(b) plan administration business for clients (not its own employees), and employees should confirm their own plan type before modeling NUA. Philadelphia, PA headquarters — PA taxes LTCG as ordinary income.
• Unum Group (UNM): 2009 contributions at ~$14/share vs. current ~$60 = 4.3:1 ratio. Meaningful for 37%-bracket employees. Chattanooga, TN headquarters — Tennessee has no income tax (repealed 2021), capturing the full federal advantage.

The general pattern: P&C insurers (Progressive, Hartford, Allstate, Travelers) have delivered far stronger stock performance since the financial crisis than life/group insurers, making P&C employees the more compelling NUA audience in this sector.

The financial crisis lot-selection opportunity

The most powerful NUA opportunity for insurance company employees is not the blended-basis approach but specific lot selection targeting crisis-era contributions. Under the NUA rules, any employer securities distributed as part of a lump-sum distribution can be NUA'd — and for purposes of determining the NUA amount, the plan's cost basis for each lot of shares is what the plan paid for those shares, not a blended average.

This means an Allstate employee can, in theory, execute a partial NUA election: distribute only the low-basis crisis-era ESOP shares in-kind to a taxable account, while rolling the higher-basis recent contributions to a traditional IRA. The lump-sum distribution requirement still applies — the entire account must be distributed in the same tax year — but the in-kind shares taken for NUA and the cash/other assets rolled over can be structured to maximize the benefit.

Here is a simplified example of the lot-selection math:

NUA-ing only Lot A (the crisis-era shares) and rolling Lots B and C to an IRA concentrates the tax benefit on the highest-ratio shares and avoids paying ordinary income on the $102,000 combined cost basis of Lots B and C in a single year — which could push the distribution-year ordinary income into a much higher bracket.

The mechanics: all assets must leave the plan in the same tax year to satisfy the lump-sum distribution requirement. The 600 Lot A shares transfer in-kind to a taxable brokerage account; the 800 shares (Lots B and C) are liquidated within the plan and the proceeds roll to a traditional IRA as cash. See the Partial NUA Strategy guide for the full lot-selection framework and 1099-R reporting mechanics.

State tax table for insurance company hub states

The bottom line: most insurance company headquarters are in states that tax LTCG as ordinary income. But major carriers have large claims centers, underwriting offices, and service operations in Texas, Florida, Tennessee, and other no-income-tax states. Employees based in those locations — not at HQ — may capture the full federal + state NUA advantage. Ask your HR department which state your plan documents consider your state of residence for tax purposes, especially if you work remotely or are nearing relocation before retirement.

Worked example: Travelers VP of underwriting, Hartford CT

Sandra Park, 60, is a VP of Commercial Underwriting at Travelers Companies, based in Hartford, CT. She has been with Travelers for 25 years (joined 2001). Her 401(k)/Savings Plan holds 2,200 shares of TRV common stock accumulated through employer match contributions over her career.

Her lot history:

• 2001–2008 (8 years): contributions at average $52/share → 923 shares, cost $48,000
• 2009–2014 (6 years): contributions at average $52/share as well (early lots near $35, later near $70) → 692 shares, cost $36,000
• 2015–2021 (7 years): contributions at average $130/share → 385 shares, cost $50,000
• 2022–2026 (4 years): contributions at average $250/share → 200 shares, cost $50,000
• Total: 2,200 shares, total cost $184,000, blended avg basis $83.64/share

Current position: 2,200 shares × $375 = $825,000 FMV
NUA amount: $825,000 − $184,000 = $641,000
Overall ratio: $375 / $83.64 = 4.5:1

Sandra is MFJ, filing jointly with her husband (also working). Their combined income puts the $184,000 cost basis distribution in the 37% federal bracket in the NUA election year.

Federal NUA path:

• Ordinary income tax on $184,000 basis at 37%: $68,080
• Long-term capital gains on $641,000 NUA at 20%: $128,200
• NIIT on $641,000 at 3.8% (her MAGI exceeds $250,000 MFJ): $24,358
• Total federal (NUA path): $220,638

Federal rollover path (full $825,000 eventually taxed as OI at 37%): $305,250

Federal lifetime savings: $305,250 − $220,638 = $84,612

Connecticut state tax: CT taxes ordinary income and long-term capital gains at the same graduated rates (up to 6.99%). Sandra owes the same CT tax whether she NUAs or rolls over — both paths result in $825,000 of income taxed at CT rates over time. State savings: $0.

If Sandra worked in Travelers' Texas operations: No state income tax on either OI or LTCG. Her total lifetime savings would be $84,612 (federal) + approximately $57,750 (CT tax avoided = $825,000 × 6.99%) = ~$142,362 total.

Pitfalls specific to insurance company employees

1. Confusing the ESOP balance with the 401(k) investment balance. At Allstate and Hartford, the ESOP and the 401(k) may appear as separate "buckets" in the plan portal. Both are part of the same plan (the lump-sum distribution must include all balances from the same plan in the same tax year), and ESOP employer stock is NUA-eligible. Verify that your plan statement shows both buckets and that cost basis is reported for each. Do not execute NUA assuming only the 401(k) balance qualifies.
2. Assuming NUA doesn't apply because "the state erases the benefit." Connecticut, New Jersey, and Ohio-based insurance employees sometimes hear from generalist advisors that state taxes neutralize NUA. This is directionally accurate (state savings are zero) but incomplete. The federal savings — which can be $80,000–$150,000+ — still applies regardless of state treatment. The state-neutrality is an argument to model carefully, not to skip the analysis.
3. Missing the basis complication from Allstate's 2022 life business divestiture. Allstate sold its life insurance and annuity business to Blackstone in January 2022. If any plan assets were reorganized as part of this transaction, basis records may have been affected. Verify lot-level basis with Voya (or current recordkeeper) before modeling.
4. Rolling ACE/pre-2016 Chubb shares to an IRA by mistake. Former original-Chubb employees who retired around the 2016 merger may have received ACE shares and immediately rolled them to an IRA under advisor guidance. This permanently destroyed the NUA election on those shares. The irreversibility of an IRA rollover is the highest-stakes mistake in NUA planning — and it happens at custodian change events like mergers.
5. Treating the recordkeeper's "taxable basis" figure as the NUA cost basis. Some plan portals display a "taxable basis" figure that is different from the plan's actual purchase cost for cost basis purposes. Always request a formal lot-level cost basis report (often called an "investment history" or "transaction history") and confirm it matches the 1099-R Box 6 basis figure before executing.
6. Not accounting for 403(b) plans at insurance company subsidiaries. Some insurance company subsidiaries — particularly those serving non-profit or educational clients — administer 403(b) plans for their own staff (not clients). 403(b) plans do not qualify for NUA under IRC §402(e)(4). Confirm your plan type by checking the "plan type" disclosure on your Summary Plan Description or calling HR.

Questions to ask your plan administrator

1. What is the plan type? (Should be a 401(k) or profit-sharing plan under IRC §401(a), not a 403(b) or 457)
2. Does my plan hold employer stock (Hartford, Allstate, Progressive, TRV, CB, etc.) as an investment option or as an ESOP contribution?
3. Can you provide lot-level cost basis records for my employer stock — purchase date, number of shares, and per-share plan cost?
4. Does the plan allow in-kind distribution of employer stock (actual share transfer, not liquidation)?
5. What is the process for requesting an in-kind distribution in my carrier's recordkeeper system (Fidelity, Voya, etc.)?
6. If I have both an ESOP component and a 401(k) investment component, are both reflected in a single plan? Can I take a lump-sum distribution covering both in the same tax year?
7. What is the December 31 deadline risk if I initiate late in the year? What is the processing time for an in-kind stock transfer?