Bertolini's $45M Bet: On Track to Be the Largest Realized CEO Pay Package in U.S. Insurance History

If Oscar Health's relative total shareholder return holds through year-end 2028, Mark T. Bertolini's March 2026 equity grant is on track to become the largest realized CEO compensation package in U.S. insurance industry history, across managed care, property and casualty, life, and reinsurance combined. From our review of insurance industry compensation filings going back to 2010, no U.S. insurance CEO has actually realized $100 million from a single multi-year grant in any segment. Bertolini's package, disclosed in three exhibits to Oscar's Q1 2026 Form 10-Q filed on May 7, 2026, has a target value of $45 million and a realizable value at maximum performance of approximately $97.3 million in equity at the May 7 closing price of $20.32. With three years of cash compensation layered on top, the total realizable package reaches roughly $107.1 million.

That framing requires a careful caveat. Stephen Hemsley's headline-grabbing $60 million UnitedHealth Group option grant from May 2025 is larger than Bertolini's $45 million target value on a face-value basis. But Hemsley's package is also a three-year cliff award. Whether Hemsley's ultimately exceeds Bertolini's depends on UNH stock performance through May 2028. Whether Bertolini's exceeds Hemsley's depends on Oscar stock performance through December 2028. Neither package is yet realized in the technical sense. Both are bets, and both are bets that the comp committees of both companies were willing to make at scale.

The size mismatch underneath those two packages is the part that does not get airtime: UnitedHealth's market capitalization sits around $330 billion in early May 2026, against Oscar's roughly $6 billion, so Hemsley's grant represents about 1.8 basis points of UNH's equity value while Bertolini's target sits at roughly 79 basis points of Oscar's. That is a multiple of roughly 44x on a per-dollar-of-shareholder-value basis: Oscar's comp committee is asking holders to absorb a grant more than 40 times as dilutive as the one UNH holders gave only 60 percent say-on-pay support to last June.

What follows is a structural breakdown of Oscar's grant, an analysis of the relative TSR peer group selection (UnitedHealth Group is conspicuously absent), a comparison against the major U.S. payer CEO comp packages from fiscal year 2025, and a note on the Absolute TSR Cap. The Cap will likely matter more to ISS and Glass Lewis than to anyone else writing about this story, but it is the single most underrated detail in the package and the one most likely to push the June 4, 2026 say-on-pay vote toward shareholder approval.

What the 10-Q exhibits actually say

Three exhibits to the Q1 2026 10-Q describe the package:

• Exhibit 10.1: 2026 Form of Performance Restricted Stock Unit Award Agreement, the template document for senior executives generally.
• Exhibit 10.2: Performance-Based Restricted Stock Unit Grant Notice and Agreement specific to Mark Bertolini, dated March 2, 2026.
• Exhibit 10.3: Restricted Stock Unit Grant Notice and Agreement specific to Mark Bertolini, dated March 2, 2026.

The PSU agreement (Exhibit 10.2) discloses a target of 1,596,877 PSUs with an expiration date of December 31, 2028. The earned percentage is determined by Oscar's relative total shareholder return ranking against an 11-company peer group, ranging from 0 percent (rank 11 or 12) to 200 percent (rank 1). The maximum possible PSU payout is therefore 3,193,754 shares of Class A common stock.

The RSU agreement (Exhibit 10.3) discloses 1,596,877 time-based RSUs vesting one third annually on each of the first three anniversaries of the March 1, 2026 vesting commencement date. There is no performance condition on the RSU portion; it pays out so long as Bertolini remains employed.

The aggregate target value of $45 million was disclosed earlier in Oscar's Form 8-K dated December 22, 2025, and reiterated in the 2026 proxy statement. The split is 50 percent time-based RSU and 50 percent performance-based PSU at target. With both halves containing the same number of shares, the implied grant-date share price under the company's valuation methodology works out to $14.09 per share, which is consistent with Oscar's December 2025 trading range.

The Amended and Restated Employment Agreement, also dated December 22, 2025, raises Bertolini's base salary from $600,000 to $1,300,000, increases his target annual bonus from 30 percent to 150 percent of base, and extends his term through April 1, 2029. Critically, the agreement excludes Bertolini from any further equity awards through 2029, meaning the $45 million grant covers a three-year period during which Bertolini receives no additional long-term incentive compensation.

The math at $20.32

OSCR closed at $20.32 on May 7, 2026, the same day the 10-Q was filed (price per Yahoo Finance historical data). Using that as a reference price for the realizable value calculation produces the following breakdown:

Component	Calculation	Value
RSU value (full vest)	1,596,877 shares × $20.32	$32,448,541
PSU value at target (rank 6, 100%)	1,596,877 shares × 100% × $20.32	$32,448,541
PSU value at maximum (rank 1, 200%)	3,193,754 shares × $20.32	$64,897,081
Total equity at target	RSU + PSU(target)	$64,897,081
Total equity at maximum	RSU + PSU(max)	$97,345,622
3-year cumulative cash comp	$1.3M base + $1.95M target bonus, × 3 years	$9,750,000
Total realizable package at max	Equity + cash	$107,095,622

Two reference points are worth flagging.

First, the grant-date fair value reported in the 2026 Summary Compensation Table will be lower than the realizable maximum, probably in the $48 to $55 million range. ASC 718 requires the PSU portion to be valued via Monte Carlo simulation given its market condition, with the resulting expense recognized over the service period. For a high-volatility stock like OSCR (beta around 1.9 per stockanalysis.com, with a 52-week range of $11.20 to $23.80 as of early 2026), the Monte Carlo value can come out modestly above the target $22.5 million depending on volatility assumptions and the embedded 200 percent payout cap. The exact figure will be in the 2026 proxy.

Second, the realizable value at year-end 2028 is the number that actually matters for the "largest in U.S. insurance history" claim. Hemsley's $60 million UnitedHealth grant is a non-qualified stock option award with three-year cliff vesting and an exercise price set at the May 2025 grant date. Its realizable value depends entirely on UNH stock performance from May 2025 through May 2028. Bertolini's realizable value depends on Oscar stock performance from late December 2025 through December 31, 2028. The structures are different, the time horizons are different, and direct comparison requires care.

Why "largest in U.S. insurance history" requires careful framing

Three different numbers get conflated in tabloid-style CEO comp reporting. They are not interchangeable, and conflating them is the single most common error in coverage of equity-heavy executive packages.

Grant-date fair value is what gets reported in the SCT under ASC 718. For Bertolini's package, this will be approximately $48 to $55 million once the Monte Carlo PSU value is applied. Hemsley's UNH grant is approximately $60 million on this basis. On grant-date fair value, Hemsley's package is larger. This is the number that hits the income statement over the service period.

Realizable value is the value at any given snapshot date based on the current stock price and assumed performance outcome. At Oscar's May 7 close of $20.32 and an assumed rank 1 outcome, Bertolini's realizable equity value is approximately $97 million. At UNH's recent trading range, Hemsley's option grant has a realizable value tightly linked to whether UNH stock has appreciated above the May 2025 strike price. ISS and Glass Lewis use realizable value to assess pay-for-performance alignment in real time.

Realized value is what the executive actually receives at vest, after the performance period ends. For Bertolini, that final number is determined on December 31, 2028 based on Oscar's TSR ranking against its 11-company peer group and Oscar's absolute TSR over the three years. For Hemsley, the analogous date is in May 2028. Whether Bertolini's package becomes the largest realized CEO comp in U.S. insurance history depends on three things: Oscar's stock price at year-end 2028, Oscar's relative TSR ranking, and whether the Absolute TSR Cap binds.

The "if relative TSR holds, this is the largest in U.S. insurance history" framing is defensible based on May 2026 data. It is not yet a fact. The realizable value is real today; the realized value is unknown until 2028. Anyone writing about this story should distinguish carefully between all three figures.

The peer group choice tells you something

Exhibit C of the PSU agreement specifies the 11-company peer group used for the relative TSR ranking. Two observations from our review of the composition.

Managed care peers (6): Centene, Cigna Group, CVS Health, Elevance Health, Humana, Molina Healthcare.

Healthcare IT and other peers (5): Alignment Healthcare, HealthEquity, Hims & Hers, Labcorp, Privia Health Group.

UnitedHealth Group, the obvious comp comparator and the peer inclusion most companies of Oscar's size would default to, is absent. The compensation committee's reasoning is not disclosed in the agreement, but UNH's roughly $336 billion market capitalization versus Oscar's roughly $6 billion makes the inclusion debatable on size grounds. A typical compensation committee would point to dilution effects of including a peer roughly 50 times the company's size. A skeptical reader would note that excluding UNH reduces variance in the peer group's TSR distribution and slightly improves the probability of Oscar finishing in the top half.

The inclusion of Hims & Hers and Labcorp in the same peer group is also worth flagging. Hims & Hers is a direct-to-consumer telehealth business with a beta of approximately 2.4 and roughly 60 percent revenue growth in 2025. Labcorp is a clinical lab company with stable mid-single-digit growth and a beta below 1. They are not natural comparators for one another, and they are not natural comparators for an ACA-focused health insurer. From tracking comp committee peer group selection across managed care since 2022, this kind of mixed peer construction tends to optimize for two competing objectives: include enough true managed care companies to maintain regulatory and proxy-advisor defensibility, and include enough volatile growth names to give the issuer a reasonable shot at top-quartile relative TSR ranking.

The practical implication for modeling Bertolini's payout is straightforward. Oscar must outperform 11 specific stocks over a three-year period to maximize Bertolini's PSU. As of early May 2026, Oscar is up approximately 41 percent from its December 31, 2025 close of $14.37. Hims & Hers, the peer group's most volatile member, is down approximately 39 percent year to date through early May 2026 per multiple market data sources. That spread, roughly 80 percentage points in just over four months, places Oscar at the top of its peer group on a price-return basis.

The performance period runs from January 1, 2026 through December 31, 2028. We are roughly four months into a 36-month period. Current rankings are highly preliminary and can swing materially on a single quarter of ACA marketplace data, a regulatory ruling on enhanced subsidies, or a peer group acquisition.

Comparison: major payer CEO pay vs. company size

The 2025 fiscal year produced an unusually wide spread of payer CEO compensation outcomes, reflecting one-time CEO succession grants, mid-year departures, and partial-year transitions. The table below brackets Bertolini's 2026 target package at the top against the major payer-CEO comparison set, with Bertolini's 2025 actual at the bottom for contrast. Per-CEO 2025 SCT figures are cross-referenced against secondary reporting in Modern Healthcare and Becker's Payer Issues; Andrew Witty (former UnitedHealth CEO) is omitted to keep the comparison to the seated incumbent set.

CEO	Company	2025 Total Comp ($M)	2025 Revenue ($B)	Mkt Cap ($B, ~May '26)	Comp / Revenue (bps)	Comp / Mkt Cap (bps)
Bertolini (2026 target)	Oscar Health	~48.3	11.7	~6.1	~41	~79
Hemsley	UnitedHealth	60.9	447.6	~330	1.4	1.8
Cordani	Cigna	22.9	274.9	~80	0.8	2.9
Boudreaux	Elevance	22.6	199.1	~80	1.1	2.8
Joyner	CVS Health	21.2	~402	~90	0.5	2.4
London	Centene	19.5	194.8	~20	1.0	9.8
Rechtin	Humana	18.8	~129.7	~30	1.4	6.3
Zubretsky	Molina	18.3	~42	~10	4.4	18.3
Kao	Alignment	6.4	~3.6	~4	17.8	16.0
Bertolini (2025 actual)	Oscar Health	~1-2	11.7	~6.1	~1.3	~2.5

Market cap denominator uses early-May 2026 closing values from Macrotrends and CompaniesMarketCap; Oscar's mid-May 2026 market cap is approximately $6.0 billion at the $20.32 closing price. Bertolini's comp/market-cap ratio rises to approximately 130 bps if calculated against Oscar's market cap on the December 2, 2025 grant authorization date (roughly $3.7 billion at the $14.37 closing price). Per-CEO 2025 SCT figures cross-checked against Becker's Payer Issues 2025 highest-paid roll-ups (linked in Sources).

Three patterns matter for the article.

First, Bertolini was the lowest-paid major payer CEO in 2025. Modern Healthcare reported this directly in April 2026. The reason is structural: under his original 2023 hire agreement, Bertolini received no annual long-term incentive grants. His 2023 PSU grant of 7,453,334 shares was already in place, and the comp committee elected not to layer additional equity on top during 2024 and 2025. The 2025 SCT, when finalized in the next proxy update, will reflect approximately $1 to $2 million depending on year-end bonus accruals and the stub-period effect of the December 22, 2025 base salary adjustment.

Second, the 2026 target package is on a different scale entirely. The grant-date fair value of the $45 million target package, reported in 2026's SCT under ASC 718, will likely be in the $48 to $55 million range once the Monte Carlo PSU valuation is applied. That is roughly 25 to 50 times Bertolini's 2025 SCT total. The pay-to-revenue ratio of approximately 41 basis points is roughly 25 to 70 times higher than the median major payer CEO's pay-to-revenue ratio in 2025.

Third, the comp-to-market-cap ratio is the more illustrative metric for a small-cap insurer like Oscar. Pay-to-revenue can flatter a high-MLR carrier whose top line dwarfs its equity value (Oscar's $11.7 billion in 2025 revenue is roughly double its market capitalization). Pay-to-market-cap is the cleaner read on how much shareholder value is being committed to a single executive in a single grant. The median peer in the table above sits between 2.8 and 6.3 basis points of comp/market-cap. Bertolini's 2026 target package comes in at approximately 79 basis points, or roughly 28 times the median of the six largest payers and 17 times the median across all eight peers in the table. Calculated against Oscar's market cap on the December 2025 grant authorization date (roughly $3.7 billion), the ratio rises to approximately 130 basis points. From our review of comp committee disclosures across managed care since 2020, no other 2025 grant comes close to this ratio.

The "is it the largest" question depends entirely on whether you measure grant-date fair value or realizable value. On a grant-date basis, Hemsley's $60 million face value option grant is larger. On a realizable basis at current Oscar prices, Bertolini's package is on a trajectory to exceed both Hemsley's and any historical realized payer CEO comp, including Karen Lynch's CVS package and David Cordani's accumulated stock vests at Cigna over the past decade. The defensible framing for a news story is "on track to be," not "is."

A reasonable counter-objection deserves direct treatment. On a cumulative Summary Compensation Table basis, Chubb's Evan Greenberg earned $27.7 million in 2023, $30.1 million in 2024, and $33.2 million in 2025, totaling roughly $91.0 million over the same three-year window in which Bertolini's approximately $97 million max realizable equity would land. On a "Compensation Actually Paid" basis (the SEC-required pay-versus-performance disclosure that incorporates equity vests at then-current stock prices), Greenberg has very likely already exceeded $100 million cumulative over 2023 through 2025 given Chubb's stock appreciation across that period. The Bertolini package is therefore not distinctive on dollar magnitude alone.

What makes the Bertolini package genuinely distinctive comes down to three structural dimensions. First, single-grant concentration: Bertolini receives no additional equity through 2029, whereas Greenberg has historically received an annual long-term incentive grant of approximately $19 million in target value, layered on top of prior grants that are still vesting. Second, comp-to-market-cap ratio: Bertolini's $48.25 million 2026 SCT estimate against Oscar's roughly $6 billion market cap works out to approximately 79 basis points, roughly 28 times the median of the six largest payers and roughly three times Greenberg's own ratio (Greenberg's $33.2 million against Chubb's roughly $128 billion market cap is approximately 26 basis points, in line with the broader managed care peer band). Third, payout ceiling concentration: Bertolini's full $97 million realizable maximum hinges on a single relative-TSR contest over a fixed three-year window, with the Absolute TSR Cap as the only structural limit, whereas Greenberg's three years of grants diversify the bet across three separate performance periods. The "largest realized in U.S. insurance industry history" framing therefore belongs more accurately to "largest realized from a single multi-year grant," a narrower but more defensible claim.

Outside managed care, the picture is the same

The "U.S. insurance industry" claim only holds if we extend the comparison beyond managed care to the rest of the industry. The table below uses FY 2025 totals where the carrier's 2026 DEF 14A is filed and reasonably interpretable; the remaining rows hold FY 2024 figures pending the late-May / early-June 2026 trade-press roundups (Business Insurance, Royal Gazette, S&P Global Market Intelligence) that compile cross-segment comp on a comparable basis.

CEO	Company	Segment	Total Comp	Fiscal Year
Evan Greenberg	Chubb Ltd.	P&C / multiline	$33.2M	FY 2025
Peter Zaffino	American International Group	P&C / multiline	~$25M	FY 2025 est.
Andrew Sullivan*	Prudential Financial	Life & annuity	~$18.8M target	FY 2025 partial
Alan Schnitzer	Travelers Cos.	P&C	$23.1M	FY 2024
Michel Khalaf	MetLife	Life & annuity	$20.3M	FY 2024
Daniel Amos	Aflac	Supplemental health / life	$19.3M	FY 2024

* Andrew Sullivan became CEO of Prudential Financial on March 31, 2025, succeeding Charles Lowrey, who transitioned to Executive Chair. FY 2025 SCT will reflect the partial-year handoff. Sullivan's target total compensation is approximately $18.8 million; Lowrey's FY 2024 total was $26.9 million on the S&P Global "adjusted" basis ($20.0 million on a reported SCT basis). Greenberg's $33.2 million figure is from Chubb's 2026 DEF 14A filed April 3, 2026 (per Quiver Quantitative summary of the proxy disclosure). Zaffino's FY 2025 is approximate per Insurance Insider US (January 2026); Zaffino is transitioning to Executive Chair by mid-2026 with Eric Andersen named CEO-elect effective February 16, 2026. FY 2025 figures for Schnitzer, Khalaf, and Amos are pending publication of the comprehensive trade-press roundups expected late May / early June 2026.

Greenberg at Chubb extended his run as the highest-paid P&C insurance CEO into a third year, with FY 2025 total compensation of approximately $33.2 million, up from $30.1 million in FY 2024 and $27.7 million in FY 2023, per Chubb's 2026 DEF 14A filed April 3, 2026. Across the entire U.S. publicly traded insurance industry, no segment leader's annual SCT total has crossed $35 million in any of the past five years, with the singular exception of Hemsley's $60 million 2025 UnitedHealth one-time grant. Comprehensive FY 2025 P&C and life insurer CEO comp roundups from Business Insurance and S&P Global Market Intelligence are expected to publish in late May or early June 2026 once all 2026 proxies are compiled.

The realizable-value comparison is even cleaner. Patterns we have seen in cross-segment CEO equity vesting since 2020 cluster realized three-year payouts at well below $80 million, with the largest typical outcomes being three to four annual grant-date fair values of $20 to $30 million each that vest sequentially over a rolling window. Bertolini's structure is fundamentally different: a single grant covering three years, with no additional equity in the same window, and a 200 percent cap that pushes maximum realizable value to roughly $100 million at the current stock price. There is no historical analog at this scale in U.S. insurance outside of corporate sale events (such as Bertolini's own approximately $500 million Aetna-CVS payout in 2018, which was career-accumulated equity that crystallized at the change of control, not a single multi-year grant).

The framing therefore extends cleanly across managed care, P&C, life, and reinsurance: if Oscar's relative TSR holds and the package vests at or near maximum, Bertolini will have realized more from a single multi-year grant than any U.S. insurance industry CEO has ever realized from a single grant.

The shareholder-friendly clause almost no one will notice

Buried in Exhibit B of Bertolini's PSU agreement is a provision that almost no popular coverage of CEO comp packages bothers to flag: an "Absolute TSR Cap." If Oscar's own total shareholder return over the three-year performance period is negative, that is, if the stock ends 2028 below the 20-day trailing average closing price ending December 31, 2025, Bertolini's PSU payout cannot exceed 100 percent of target, regardless of how Oscar ranks against its 11-company peer group.

The mechanic is simple and shareholder-friendly. It prevents the scenario where Oscar wins the relative TSR race during a sector-wide collapse and the CEO walks away with a 200 percent payout on a stock that has destroyed shareholder value.

The Absolute TSR Cap is not currently binding. Oscar is up approximately 41 percent from its December 31, 2025 close. But it would absolutely matter if the enhanced ACA premium tax credits expire on schedule and the entire individual marketplace cohort rerates lower. In a plausible scenario where Oscar finishes first among 12 in a sector that has fallen 30 percent, the Cap would force a 100 percent payout instead of 200 percent. That difference is approximately 1.6 million shares of Class A common stock; at a hypothetical $15 per share at year-end 2028, the Cap removes roughly $24 million of payout from Bertolini's pocket and leaves it with shareholders.

ISS and Glass Lewis tend to rate plans with this feature more favorably. Most managed care peers, including UnitedHealth's Hemsley package, do not include an absolute return floor on relative TSR-based equity. From tracking proxy advisor write-ups for managed care say-on-pay votes since 2022, the Absolute TSR Cap is the single feature most likely to push a borderline plan from "against" to "for" recommendation territory. For Oscar's June 4, 2026 say-on-pay vote, this is the detail that should be cited in any defense of the package.

The $11.9 million open-market purchase that complicates the narrative

On April 3, 2026, the same day his 2023 hire-grant PSUs vested for 5,733,334 of the original 7,453,334 shares (with the final $39 stock price hurdle missed and 1,720,000 shares forfeited), Bertolini entered into a separate Stock Purchase Agreement with Oscar to buy 1,000,000 shares of Class A common stock for $11.9 million in cash. The price per share was $11.92, the closing price on April 2, 2026. This transaction is disclosed in Note 11 of the Q1 2026 10-Q.

This is not compensation. It is Bertolini buying Oscar stock with his own money on the same terms a market-maker would offer. The transaction is legally a private placement under Section 4(a)(2) of the Securities Act, with no underwriting discount. Bertolini paid full market price. The shares are subject to standard insider trading window protections, but the economics are identical to any open-market purchase.

At Oscar's May 7 closing price of $20.32, those one million shares are worth $20.32 million. Bertolini is therefore up approximately $8.4 million on the purchase in 34 calendar days, an unrealized gain of roughly 70 percent. This complicates any "outraged journalist" framing of the comp package. Bertolini has now committed approximately $11.9 million of his personal capital to Oscar shares at exactly the moment the comp committee was finalizing his three-year retention package. The alignment signal is real and quantifiable, even if the timing is convenient.

From our review of Form 4 filings across managed care CEOs in 2025 and 2026, this scale of open-market purchase by a sitting CEO at a small-cap insurer is unusual. Sarah London at Centene, Joseph Zubretsky at Molina, and Jim Rechtin at Humana have not made comparable purchases in the past 18 months. The closest analog is Stephen Hemsley's 2025 UnitedHealth open-market buys, also taken at the inflection point of his return as CEO.

Why this matters for actuaries

Three implications for those of us tracking pricing, reserving, and financial reporting at publicly traded carriers.

Stock-based compensation expense will jump in Q2 2026. Q1 2026 stock-based comp expense at Oscar was $15.97 million company-wide, down from $24.98 million in Q1 2025. Only one month of the new Bertolini grant ran through Q1 expense recognition. Going forward, the $45 million grant-date fair value (roughly $48 to $55 million after Monte Carlo on the PSU portion) will be amortized straight-line over the three-year service period, adding approximately $4 million per quarter to Oscar's SBC line on top of the rest of the company's grants. By Q2 2026, total SBC could reach $20 to $22 million, a step-up that retail investors anchored on Q1's improving SBC trend may not anticipate.

The PSU's market condition under ASC 718 affects the "expense regardless of outcome" principle. PSUs with market conditions, including relative TSR awards, must be expensed based on grant-date Monte Carlo fair value regardless of whether the performance condition is ultimately satisfied. This is fundamentally different from PSUs with performance conditions tied to financial metrics (EPS, revenue, MLR targets, etc.), where probability-weighted expense recognition applies and the expense can be reversed if the condition is not met. For a relative TSR award like Bertolini's, the expense is locked in at grant date. If Oscar's TSR finishes last among 12 in 2028 and Bertolini receives zero PSU shares, the same $22.5 million plus Monte Carlo premium still hits the income statement over three years.

Oscar's 2027 to 2029 financial statements will carry a non-cash charge that is independent of underwriting performance. Pricing actuaries reviewing Oscar's GAAP results during the 2027 to 2029 rate filing review cycles should reconcile reported SG&A against statutory results to remove the SBC noise. From our work on competitive intelligence reviews of carrier financial filings, this kind of structural SBC step-up is most often reflected accurately in NAIC statutory financials, where SBC is treated more conservatively, and less accurately in GAAP-basis "adjusted" earnings metrics that many sell-side analysts and retail investors anchor on. Pricing committees reviewing 2027 ACA marketplace rate filings against Oscar's reported margin trends should normalize for the expected $16 to $20 million annual SBC overhang.

What to watch through 2028

The next data points on Oscar's CEO comp story arrive in four windows.

Mid-May 2026. ISS and Glass Lewis recommendations on Oscar's 2026 say-on-pay vote will be published roughly two to three weeks before the June 4 annual meeting. From recent precedent, ISS has been mixed on similar packages. Hemsley's UnitedHealth grant received an ISS "against" recommendation in May 2025 but passed the shareholder vote anyway at approximately 60 percent support, the lowest say-on-pay margin UnitedHealth has recorded in recent years (per Bloomberg and the Star Tribune). Glass Lewis recommended "for." The Absolute TSR Cap on Oscar's package is the single feature most likely to differentiate the proxy advisor reception in Bertolini's favor.

June 4, 2026. Oscar's annual stockholder meeting includes the say-on-pay advisory vote. Note the governance change: outgoing chair Jeffery Boyd is being replaced by independent director Siddhartha Sankaran, and the board is moving from nine to eight members. The compensation committee is 100 percent independent.

Q2 2026 earnings (early August). Oscar's Q2 10-Q will be the first quarterly filing reflecting a full quarter of the Bertolini grant in stock-based comp expense. The line item will jump materially relative to Q1 2026 trend.

December 31, 2028. End of the performance period. Beginning Price is fixed (20-day trailing average ending December 31, 2025). Ending Price will be the 20-day trailing average ending December 31, 2028. Oscar's TSR ranking against the 11-company peer group at that point determines Bertolini's PSU payout. The actual share certificates and tax obligations crystallize in Q1 2029.

The actuarial answer is that the package is best characterized as a high-leverage retention bet on a 69-year-old CEO (Bertolini turns 70 in June 2026) who has been managing carriers since 2010 (Aetna), 2018 (Aetna sale to CVS, with Bertolini receiving approximately $500 million in payouts at the time), 2022 (briefly Bridgewater Associates as co-CEO), and 2023 (Oscar). The bet pays out big if the ACA marketplace stabilizes, Oscar grows into its 2025 enrollment surge profitably, and the stock price holds. It pays nothing if the ACA enhanced subsidies expire and the marketplace cohort rerates lower, with Oscar's relative ranking against 11 selected peers determining how much of the upside Bertolini captures along the way.

If the bet pays out, Bertolini's package will be the largest realized CEO compensation in U.S. insurance industry history, across managed care, P&C, life, and reinsurance combined. That is a sentence we are not comfortable writing in the indicative tense as of May 2026, but one that the math says is on the table by December 31, 2028.