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In general, professionals track every wager as an investment, with wins offset by losses. There are specific criteria used to limit what can be offset--no shoeboxes of losing tickets with heel marks scooped up from the racetrack floor after a winning day, and no "unusual" wagers. The latter, if contested, must be shown to be the result of a specific pattern--not a wild flyer. For example, a $20 bettor suddenly switching to $300 wagers and "suffering a string of losses after a big win" is likely to be questioned with skepticism.
Unless there is a specific investment plan in which each individuals contribution is clearly defined (as in an LLC), any attempt to "spread the grief" after a major win is likely to flop badly. I do not intend this comment to be construed as legal advice, or as an attempt to provide legal advice, but the best recommendation is to avoid that "syndicate using one guy's ADW" like the plague.
If one cannot do well enough to happily pay whatever taxes are owed as a result, one needs to spend more time improving his or her handicapping and keeping accurate, detailed records acceptable to the IRS. Either that, or take up macrame or needlepoint.
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