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Scott Boras’ fractured history with the Toronto Blue Jays

If someone described this scene to you, you might think it was a fever dream. There’s Charlie Montoyo wailing away on a set of bongos while super agent Scott Boras bobs his head to the beat and Hyun-Jin Ryu and his wife wonder what they’ve signed themselves up for.

Everything about the setting seemed made up, but the most perplexing part was the fact that Boras — a man who publicly criticized the Blue Jays organization for the past 34 years — suddenly had a change of heart.

The commission on Ryu’s $80 million contract certainly helped repair a relationship that’s been contentious for over three decades. At one point in time, Blue Jays president Paul Beeston swore off signing Boras clients altogether. Now, the Blue Jays helped the Boras Corporation cross the $1 billion dollar threshold this offseason.

To appreciate how far the Blue Jays’ relationship has come with Boras, one has to look back at how fractured it was from the start.

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1985: Boras flies a plane over Exhibition Stadium that says “JIMY – GIVE CAUDILL THE BALL”

Bill Caudill was the very first player that Boras represented in the early 80s, and he brokered a record-setting deal for his client: a five-year, $7 million contract. It represented the largest free agent deal for a Blue Jays player and it made Caudill the second-highest paid pitcher in the game.

Caudill was only one year into his Blue Jays tenure before things went sideways. Tom Henke usurped him as the team’s closer by mid-1985 and Caudill resorted to pitching in low leverage situations. Not pleased with the way Caudill was being used by the manager Jimy Williams, Boras took matters into his own hands.

According to this note from the July 7, 1986 edition of Sports Illustrated, Boras pulled his first publicity stunt:

An airplane passed over Toronto’s Exhibition Stadium on June 25 carrying the following message: JIMY—GIVE CAUDILL THE BALL. The hint to Blue Jays manager Jimy Williams was paid for by Bill Caudill’s agent, Scott Boras.

2009: The James Paxton debacle

James Paxton is one of the Blue Jays’ classic tales of “the one that got away” (Kris Bryant is another) as a player who was drafted by Toronto, but who couldn’t come to an agreement.

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The Blue Jays drafted Paxton 37th overall in the 2009 MLB Entry Draft and it was up to Paul Beeson to broker a deal with Paxton’s agent: Boras. Therein lied the problem; according to the NCAA, players aren’t allowed to have “agents”, only “advisors”.

Beeston let it slip in an interview with John Lott that the Blue Jays had been negotiating with Boras, which tipped off the University of Kentucky and they suspended Paxton. Here’s what Beeston had to say about the negotiations with Boras:

“They were cordial. They were firm. They were businesslike, and they took a while. I couldn’t convince him and he couldn’t convince me. Things have never changed between us.”

Ultimately, the Blue Jays received a compensation pick for failing to sign Paxton, who turned into Noah Syndergaard. The Blue Jays emerged with a quality pitcher in the deal but didn’t do themselves any favours by botching the contract talks with Paxton and Boras.

2014: Boras calls out Rogers for not spending

2013 was a complete disaster for the Blue Jays, and rather than doubling down on their efforts to reach the postseason, the team stayed pat during the offseason of 2013.

With Boras holding many high-priced clients, many who could have improved the Blue Jays, Boras called out the Jays and Rogers for not increasing their efforts to put a winning team on the field in 2014: From The Toronto Sun:

“There is no one who has the asset base of Rogers. It’s a premium city. It’s a premium owner with equity. And it’s a very, very good team that with additional premium talent could become a contending team.

They’re a car with a huge engine that is impeded by a big corporate stop sign … a successful and committed ownership that needs to give their baseball people financial flexibility.”

2017: Boras goes on the offensive after Sanchez’ arbitration case

After a breakout campaign in 2016, Aaron Sanchez deserved to be paid more than the league minimum in 2017. But as a standard practice for players with one to three years’ service time, teams typically only offer players a slight pay increase. Clubs don’t just hand out free money.

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Boras didn’t see it that way. When Sanchez refused a slight salary increase for the 2017 season, he instead settled on being paid the league minimum, which was $535,000. This incensed Boras, and he voiced his displeasure loud and clear. From Sportsnet:

“Toronto is so rigid, they not only have a very antiquated or substandard policy compared to the other teams for extraordinary performance, but if you don’t accept what that low standard is, they then have the poison pill of saying, you get paid the minimum.

It’s the harshest treatment in baseball that any club could provide for a player. That’s why few teams have such a policy.”

2018: The “Blue flu”

Major League Baseball is enjoying a banner year in terms of offseason spending, but last year wasn’t the same case. It wasn’t until the New Year when big contracts started falling into place, but free agent spending was stagnant until early January of this year.

The Blue Jays were among the many teams in baseball who took the frugal approach in the offseason and as Boras is known to do, was armed with a classic Boras-ism about the lack of spending by the Blue Jays. From The Toronto Sun:

“Toronto is a wonderful city. It’s been a great franchise. They’ve drawn three million fans. They’ve lost near a third of their fan base due to the Blue Flu of not bringing attractive players that their fans find interesting to their market.”