You cannot Net them against each other. Make sure to understand what are the distribution/withdrawal provisions first, for this person and for that account (because you stated SIMPLE IRA and there is a 25% tax potential) in addition to the 10% penalty you mentioned:

https://www.irs.gov/retirement-plans/retirement-plans-faqs-regarding-iras-distributions-withdrawals

Bob's question relates to the rollover provision. But contributions through the paycheck year are not likely to meet the rollover provision. You'll have to research the details to see what applies per this person's activities.