The danger of lengthy contracts is one of the main reasons why Anthopoulos prefers to do almost all of his business through trade as opposed to free agency. There was one exception last offseason, when the Blue Jays considered a six-year offer to an undisclosed free agent, but for the most part, it's a rule Toronto simply won't break.
"When I was an [assistant general manager], my mind-set was a little bit different; I was probably more open to longer deals," Anthopoulos said. "I've seen some of these deals not work out for some clubs and how quickly things change with players.
"There are some players out there in trade that signed long-term contracts, and then a year or two later, they're already getting moved. That's pretty telling. I still think five years is a long period of time."
Anthopoulos conceded that because of the self-imposed limit, a certain group of players simply isn't available to them. In a lot of cases, though, there are ways to get around the issue without compromising the rules.
Toronto typically would offer a shorter-term contract that includes a higher annual salary to help offset the overall difference. Anthopoulos used an example of an unnamed player who signed for more than five seasons but would have agreed to a five-year deal at a higher annual rate.
What the Blue Jays want to avoid is having to essentially eat money at the end of a deal because they know the production won't be there six, seven or eight years down the road.
"That's certainly a choice, and some clubs choose to do that," Anthopoulos said. "We've obviously chosen not to do that, but that can definitely be a thought process. I think at the end of the day, if you're eating the last two or three years of the deal, if you're representing the contract appropriately to your ownership, you say these last two or three years don't mean anything.
"Lump those into the first three or four [years], and that's ultimately what you're paying the player. Just go shorter and pay him. Dump in the money, it's the same thing. If we're going to go seven times 10, or go five times 14, it balances out at the end of the day."
Gregor Chisholm is a reporter for MLB.com. Read his blog, North of the Border, and follow him on Twitter @gregorMLB. This story was not subject to the approval of Major League Baseball or its clubs.