Prior research has shown that even the most subjective fair value estimates are value-relevant (Song et al. 2010, Kolev 2009, Goh et al. 2009) and that managers appear to use Level 3 valuations opportunistically (Valencia 2011, Fiechter and Meyer 2009). However, the association between “traditional” measures of aggressiveness in financial reporting and biased estimates of fair value has not been previously studied. I test whether aggressiveness, as measured by discretionary accruals, real activities manipulation, and meeting-or-beating analysts’ consensus estimates, is positively associated with realized and unrealized gains and losses on Level instruments. Overall, I find limited support that aggressive firms opportunistically use fair value measurements to overstate earnings. Inferences remain the same whether only the unrealized component of gains/losses are examined and whether firms are classified into “suspect” or “non-suspect” groups.