Yes, he could. If Phil was streaming it. However, I still surmise that he's writing off WWE Champions on his business losses, like he does with his subscriptions to Xbox, Sony, Nintendo, etc...Why? Because he thinks that the idiots at the IRS won't spot it. However, all it would take is one forensic accountant to spot the crimson flags to look further into it. However, in everything Phil related, future Phil is gonna have to pay for the actions of past Phil.
However, it's gonna bite him in the ASS! All it would take it is a forensic accountant to spot the irregularities on his earning and loss reports that he has to submit to the IRS every year for them to go "Hmmm, that's interesting." However, the IRS is about "Give them rope, let them hang themselves." I'll give you an example: if you're making $30K a year, but you're writing off hundreds of thousands of dollars in losses in stocks, bonds, etc...normally, that's a red flag. Even if you were a doctor or lawyer for most of your professional career, that's unheard of to write off those kind of losses in one year and would constitute for a forensic accountant to step in and take a look at your ledger.
In Phil's case, there are NUMEROUS crimson flags that would make any accountant go "I want to see your ledger." The fact that Phil didn't have a separate business account that was separate from his personal checking account was a MAJOR flag that would make anyone go "Yeah, this isn't right." Do I think that day will ever come when Phil gets a letter from the IRS saying that they want to do a through investigation of his ledger? Not holding my breath, but weirder things have happened.