Although she might not have reasonably contemplated the loss, the court in Canalin v. Thikol awarded damages for future lost profit. Mr. Smith would probably not have a good claim for the dog's sale to the breeder. A final issue is whether Mr. Smith can collect for punitive or aggravated damages. Anne's action was negligent but not vindictive. Also the courier does not kill dogs as a matter of policy nor did it benefit from the act.
Punitive damages are unlikely.
Issue number 1 in this question is whether Reid can collect his 2000,000 from Prince University. The University did not receive anything new and Reid did the thing he was already obliged to do so the contract appears to be void. The British courts have taken a different approach and this might be persuasive in a Canadian court. In William v. Finally there is the issue of unconscionability or economic duress.