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.

Dave Stewart

Signed a two-year, $8.5 million deal on Dec. 8, 1992
Grade: B

Stewart was the 29th highest earner in 1993 and 33rd in 1994. Stewart produced 2.5 bWAR in his two seasons with the Blue Jays, but his overall numbers were not great, as he had a 5.09 ERA with 207 strikeouts in 295 1/3 innings in his two years with the Blue Jays.

Still, he stifled a talented White Sox club in the ALCS in 1993, and, without his 2.03 ERA in 13 1/3 innings that series, there’s no guarantee the Blue Jays repeat as World Champs.   

Rogers Clemens

Signed a four-year, $40 million deal on Dec. 13, 1996
Grade: A

Clemens had two of the most dominant seasons on the mound in Blue Jays history.

He was the fourth-highest paid player in MLB in 1997, and fifth-highest in 1998. Clemens won back-to-back Cy Young Awards, was an All-Star in back-to-back seasons and produced 20.1 bWAR across 498 2/3 innings in those two years.

He threw recorded a 2.33 ERA with 563 strikeouts in those innings, and went 41-13 — which is 25% of the 164 games they won over those two seasons. He was traded traded to the Yankees in the third year of that deal.

Carlos Delgado

Signed a four-year, $68 million deal on Nov. 6, 2000
Grade: A

Delgado's extension shot him into the upper echelon of MLB’s highest earners, as he ranked in the top-three earners in baseball from 2001 to '04.

Delgado produced 18.2 bWAR over the course of this extension and slashed with 282/.405/.555 with 146 home runs during his age 29-32 seasons.

He led the league in RBI, OPS and OPS+ in 2003, and was also named an All-Star that season.

While you can’t say Delgado gave the Blue Jays a hometown discount, this signing kept a homegrown star player in town for a couple more years and paid him pretty much exactly what he would’ve been worth on the open market.  

A.J. Burnett

Signed five-year, $55 million on Dec. 6, 2005
Grade: C

Burnett signed one of the most interesting contracts in Blue Jays history when he inked a five-year, backloaded deal full of opt-outs.

In his first year of the deal, a 29-year-old Burnett made just over $2 million, and, aside from some injuries, had a relatively effective season. He had a 3.98 ERA in 135 2/3 innings.

The next year his salary jumped to $13 million, making him the highest-paid member of the team, and the 26th-highest paid player in MLB.

Over those final two seasons, Burnett was worth 4.8 bWAR. He led the league in strikeouts in 2008 (231), opted out of his deal and signed a five-year $82.5 million deal with the Yankees.

Roy Halladay

Signed a three-year, $40 million extension on Mar. 23, 2006
Grade: A

This extension technically didn’t kick in until the 2008 season (where Halladay made $10 million and was the 74th-highest paid player in the league) before his salary got bumped up to $14.25 million the next year, which was the 28th-highest contract in MLB.

Halladay produced a 13.2 bWAR over 485 innings in those two years. He struck out 414 and had 155 ERA+ in 65 starts. He also threw 18 complete games. Halladay was traded in the Phillies in the final year of his contract.

Vernon Wells

Signed a seven-year, $126 million contract on Dec. 15, 2006
Grade: B

Wells signed a weirdly structured deal that was the sixth-richest deal in MLB historyat the time of his signing. The deal had a ton of signing bonus money deferred over the length of the deal and Wells’ yearly salary was only $500,000 in 2008 and $1.5 million in 2009.

It then jumped to $12.5 million in 2010 and $23 million in 2011.

Wells then received $21 million in each of the final three seasons. Wells also only made it to the third year of this deal before being traded to the Los Angeles Angels. He only spent two years with the Angels before being traded to the Yankees, who paid off the last two years of the deal

During his three years with Toronto on this deal, Wells was worth 6.9 bWAR with a slash line of .275/.327/.466.

Those are good numbers for a guy who wasn't even in the top 100 of player salary thanks to the structure of the deal. He was 24th in the league in earnings in 2010 before becoming the second-highest paid player in 2011 — as a member of the Angels.

Wells' deal was the last time the Blue Jays signed a player to a deal that was in the top-30 of salary until they signed George Springer to his six-year, $150 million deal ahead of the 2021 season.