<prompt> Human: My boss recently let me know I would be receiving a bonus for this past years performance of approx 30k. I asked him to wait until January so I can claim it on next years taxes. I also would be maxing out my 401k contribution portion of the bonus as well as a little additional just to play catch up. Bottom line is I would still be paying quite a bit of taxes on the bonus.He called me today and suggested that instead of a bonus, he would be happy to buy me a new vehicle I am currently in the market for one. He would purchase it through the company and then sell it to me for 500 or something to that effect. He figures Ill be getting the full value of the bonus that way rather than paying so much into taxes. Does this make sense? Is it really a better deal? I could use some advice. Thanks in advance PF! EDIT - Thanks all! I really love this place. I will talk to him about the best possible and legal! solution. He definitely wasnt trying to fleece the gov, just looking out for me albeit without much forethought. Thanks again for your advice and I hope everyone has a healthy and prosperous new year!Assistant: Huh? Does this company have a legal department? This would be fraud. If companies could avoid taxes this way, everybody would do it. Human: Ha! We definitely do not have a legal dept. This is a small construction company. I dont think that my boss is looking at it as anything other than a help to me. He is just trying to get me the most value out of my bonus. I am a bit naive with this sort of thing so I thought Id ask. Deep down I know that its probably to good to be true. How would that work, would I then need to pay taxes on the gift?  <response>: Yes, the difference between what you paid and the amount the company spend would be considered income, just as much as cash would be. Keep it simple and take the cash. Your boss will be super unhappy if the company were to get audited after doing this. 