Cboe Global Markets (CBOE) RSU sell-vs-hold
Calculator · free · no signup · CBOESell at vest or hold? Compare after-tax payout from selling Cboe Global Markets RSUs at vest vs. holding through the LTCG cliff at 12 months.
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Your vest
Tax inputs
Hold strategy
Best after-tax payout — at year 1 yr
$47,709
Sell + invest wins by $4,981 over Hold 1 yr.
Estimates only. Not financial advice.
Heads-up: under-withholding. Your employer withholds federal tax at the IRS supplemental rate (22.0% on this vest, ≈ $17,600). Your marginal federal rate on this vest is 32.7%, owing $26,171. Expect to settle the $8,571 gap at tax time.
The hidden purchase
Tax was paid at vest either way. Holding is mathematically equivalent to taking $44,509 in after-tax cash and buying $44,509 of CBOE today.
Most diversification frameworks would advise against a purchase that size in a single name; the right answer depends on your conviction in CBOE. Holding past one year converts the gain to LTCG.
Sell + invest
Best payout| Vest value (shares × price) | $80,000 |
| Federal | |
| State | |
| Medicare | −$1,160 |
| Additional Medicare | −$720 |
| Market gain over 1 yr at 10.0% | $4,451 |
| Cap-gain tax on diversified gain — LTCG (federal + state + NIIT) | −$1,251 |
| Net at year 1 yr | $47,709 |
Sell every share at vest; invest the after-tax cash at the market return for 1 yr, then liquidate. Diversified — no single-stock concentration risk.
Hold 1 yr
| Vest value (shares × price) | $80,000 |
| Vest tax (federal + state + FICA) | |
| Net at year 1 yr | $42,728 |
Sold 444 shares to cover vest tax (net-settled); kept 556 shares 1 yr to qualify for long-term capital gains.
Social Security + Medicare are payroll taxes (collectively called FICA) — they apply because you're still employed at vest.
Both columns are stated in year-1 yr dollars. The sell side compounds at the market return; the hold side compounds at your single-stock expected return after a 20% volatility drag.
Estimates only. Assumes net-settled (sell-to-cover) vesting; double-trigger and pre-IPO RSUs are out of scope. Excludes multi-state moves, AMT interactions on other equity, and 83(b) elections. Not financial advice.
You evaluated one RSU vest. The beta plans every vest of every grant across years, with concentration and AMT in the loop.
Request beta access →Related calculators: RSU Lot Order Calculator · Stock Concentration Calculator
About Cboe Global Markets
Cboe Global Markets (CBOE) is a public Fintech company, incorporated in Delaware and headquartered in Chicago, IL.
Last close: $271.26 per share (as of 2026-10-03).
Equity grants at Cboe Global Markets typically include restricted stock units (RSUs).
Cboe Global Markets, Inc. is an American financial exchange operator. In the U.S., it owns the largest exchange for trading in options, where it has a 30% market share, and the third-largest exchange for trading in equities, where it has a 10% market share. It operates the largest stock exchange in Europe, where it has a 25% market share. It is headquartered in Chicago, where it maintains an open outcry trading floor.
Source: Wikipedia (CC BY-SA 4.0)
The Chicago Board Options Exchange opened in 1973 as the first marketplace for listed options and still owns the proprietary index products built on that history, principally options on the S&P 500 and the VIX volatility index. Exclusive licensing on those indices means the trading cannot migrate to a competing venue, which is a materially better position than the fee competition in equities. Volatility is good for volume, so revenue rises when markets are unsettled. Market data and access fees supplement transaction revenue. Headquarters are in Chicago.
Sources: sec.gov · en.wikipedia.org
Equity comp at Cboe Global Markets
- Cboe's RSU award agreements use double-trigger vesting: a change in control alone does not accelerate vesting. Acceleration only occurs if the employee is terminated without cause (or resigns for good reason) within two years after the change in control, or if the acquiring company will not provide a replacement award. Separately, RSUs also vest early on the holder's death, disability, or qualified retirement, which is a more generous provision than many peer companies offer.
- Early exercise is not allowed: you have to wait for shares to vest before you can buy them.
- RSUs use double-trigger vesting. Two things must both happen before the shares are yours: (1) the normal time-based vesting completes, and (2) the company has a liquidity event (an IPO or an acquisition). Until both happen, you do not yet own the shares and you do not owe tax on them.
Researched 2026-08-21.
OptionsAhoy is an independent tool and is not affiliated with, endorsed by, or sponsored by Cboe Global Markets.
Cboe Global Markets (CBOE) RSUs vest as ordinary income at the price on vest day. The decision is whether to sell at vest and reinvest, or hold the shares through the 12-month LTCG cliff. This calculator runs both paths through the same after-tax math so you can compare like-for-like.
Example: 500 Cboe Global Markets (CBOE) RSUs vesting at $271.26 per share is $135,630 of ordinary income on vest day. After roughly 32% combined federal + state + FICA (~$43,402), the post-tax share value is ~$92,228. Holding 12 months for long-term capital-gains treatment then only matters for the price change between vest and sale; the ordinary income at vest is already locked in. The calculator runs both paths through the same after-tax math.
All Cboe Global Markets tools → · Use the generic RSU Sell-vs-Hold Calculator for any company. Diversifying multiple RSU lots? See the lot-by-lot sell order →
Cboe Global Markets equity questions
- Should I sell or hold my Cboe Global Markets RSUs at vest?
- Cboe Global Markets restricted stock units (RSUs) are taxed as ordinary income on their value at vest whether or not you sell. The only open decision is what to do with the shares afterward: sell at vest and reinvest, or hold past twelve months for long-term capital-gains treatment on any further gain. The calculator above runs both paths through the same after-tax math so you can compare them directly.
- Does Cboe Global Markets grant ISOs, NSOs, or RSUs?
- Equity compensation at Cboe Global Markets typically takes the form of restricted stock units (RSUs). Restricted stock units are taxed as ordinary income when they vest.
- Does Cboe Global Markets allow early exercise of stock options?
- No. Cboe Global Markets requires options to vest before you can exercise them, so the holding-period clock for long-term capital-gains treatment starts as each tranche vests and you exercise it.
- Do Cboe Global Markets RSUs use double-trigger vesting?
- Yes. Cboe Global Markets restricted stock units (RSUs) vest only when two things both happen: the time-based schedule completes, and the company has a liquidity event such as an initial public offering (IPO) or an acquisition. Until both occur you do not own the shares and owe no tax on them.
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