"""and what's a 40k truck worth to a future lawyer trying to make a million?"""

Well.. $40,000.

Those who know way more than I do about boxing don't give Joey a chance of winning. So does Joey really think he has a chance of winning the $1,000,000? Not if he is as smart as you think he is.

There are lawyers and then there are Lawyers. Lawyers that hustle and/or land jobs with big firms can make big bucks. But there are a lot of people with law degrees that sit around an office all day long waiting for the phone to ring. And/or work as paper processors for Credit and Collections companies. Or leave the profession altogether. Since Joey graduated Thomas Jefferson school of law in May 2003, and didn't pass the Bar exam till June 2004, one can reasonably conclude that Joey took at least two tries, and possibly three to pass the Bar exam (70% of first time test takers pass their first time). Additionally, TJsol is ranked near the bottom of US law schools http://www.ilrg.com/rankings/law/index.php/2/asc/LawSchool

Based on those facts, I think I can confidently say that Joey does not fall into the 'future big time Lawyer' category. So, whether Joey knows it or not, giving away a $40,000 truck was a stupid move (unless Sly already had some side deal with Joey).