Lindsay Lohan is "winning" with her latest friendship.

Charlie Sheen and Lohan got close while filming "Scary Movie 5," and Sheen is helping out the actress in a big way, TMZ reported Sunday.

Lohan reportedly owes $233,904 in back taxes for 2009 and 2010, and Sheen has given the "Liz & Dick" star $100,000 to help her pay the IRS, the website reported.

So what does this mean for Lohan's financial woes?

If Sheen gifted the money to Lohan, he could have either paid it directly to the IRS on her behalf, or given it to her to deal with, Federal Tax Practitioner David Selig explained to FOX 411.

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"If the concern was that she would just fritter [the money] away it's not uncommon to pay it to the IRS." Selig, of Selig & Associates Inc., explained.

But even the "Anger Management" actor gave the gift directly to the IRS, LiLo will likely have to pay taxes on the money, which would be categorized as income for 2012, Selig said.

"I have to believe that the motivation is mixed bag. First of all, it creates publicity, and secondly, it may be an attempt to help a dear friend. Either way the Internal Revenue Service will want their share."

Representatives for Sheen, 47, and Lohan, 26, could not be reached for comment.