Grading the largest contracts in Toronto Blue Jays history

Earlier this week, the Toronto Blue Jays locked Vladimir Guerrero Jr. into a 14-year $500-million deal that they hope will kick open the team's next contention window.

After losing out on Shohei Ohtani, Juan Soto and several other notable free agents the past few seasons, Toronto inked a legitimate superstar to the second-richest contract in league history.

The contract has certainly raised eyebrows around the league, and it sends a signal to other players that they are willing to open their wallets and spend big-time for big name players.

However, it’s not the first time Toronto has decided to ink a player to a large contract.

Throughout the nearly 50 years of Blue Jays baseball, there have been several times they signed players to contracts that were among the leagues richest at the time.

With Guerrero's contract in mind, lets take a stroll down memory lane and break out the red ink to grade how those deals aged.

Note: this list was narrowed down to only include players who were among the top-30 in payroll All contract information was taken from Spotrac.com. This list doesn’t include any current Blue Jays.

How did the biggest contract signings in Blue Jays history turn out?

Jack Morris

Signed to a two -year, $10.85 million on Dec. 18, 1991
Grade: B

Before inking Morris to a deal, the Blue Jays had just lost to him and the Minnesota Twins in the 1991 postseason, after spending the better part of the last decade battling Morris when he was with the Detroit Tigers.

But Morris went from heel to hero when he signed his two-year deal with the Blue Jays. His deal was one of the signed one of the biggest contracts in MLB at the time, as he became the fifth-highest paid pitcher in MLB.

While Morris wasn’t statistically great during the two-year contract (4.87 ERA with 235 strikeouts in 393.3 innings) he gave the Blue Jays a legitimate horse at the front of their rotation for their first World Series victory.   

Joe Carter

Signed a three-year, $19.5 million deal on Dec. 7, 1992
Grade: A

Carter hit the home run that won the Blue Jays their second World Series title; how can this be anything other than an A?

Carter was the highest-paid player in the American League on the team with the biggest payroll in baseball in 1993, and he was worth every penny during that magical season.

Carter’s deal went from his age 33 to 36 seasons (it had an option that included a fourth year) and during that time he mashed 115 home runs while .257/.309/.477 and earning three All-Star nods.