The recent contract given Roy Halladay is a good example of how an inexperienced Agent can hurt you. Despite back loading the deal for the teams' benefit Greg Landry, who did most of the work on Halladay's deal & hadn't done a large deal like this before, failed to negotiate even a deferred signing bonus into the deal.
Why is that important?
#1) In Halladay's tax bracket he will pay the highest tax rate(approx. 40%) on all income both in Canada & the US. Taking only $2 million in a Signing Bonus(in a back loaded $42 million deal he should have gotten $5mill.-$6 mill. if he took a deferred bonus)would have saved him at least in excess of $500,000 a lot of money even when you sign for $42 million.
How would that save him anything? In Canada Signing Bonuses are taxed @ only 15% & in the US there is no Social Security witholding on a Signing Bonus.
#2) Signing Bonuses are paid in a lump sum salaries are paid in incremental payments. If Halladay took a Signing Bonus & invested it in almost anything, in addition to saving the tax money he would have earned money on his money.
For this he also had to pay Landry's commission. A bad deal anyway you slice it.