The World Series kicks off on Friday. Do you know what that means? It’s almost Transaction Season.
The big talk around Blue Jays land over the past few days has been about Hyun Jin Ryu, specifically the insurance on his contract. The Twitter account Blue Jays Hotstove brought up that the Blue Jays fully ensured Ryu’s contract and that they’ll allocate the money they were expecting to pay him back into the payroll for 2023…
This is something that’s been talked about quite a bit in the past but the details are a little murky.
Ryu, of course, inked a four-year, $80 million deal with the Blue Jays back in December of 2019. He had an excellent showing in the pandemic-shortened 2020 season, started off well in 2021 but faded as time went along, and then completely fell off early in 2022 and wound up having season-ending elbow surgery in June. There’s a chance that Ryu comes back late in 2023 but the reasonable bet here is that he’s thrown his last pitch for the Blue Jays.
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Given Ryu’s injury history (he missed all of 2015 and most of 2016 after undergoing shoulder surgery and was limited to 15 starts in 2018 because of a groin injury), having his contract insured would have been the prudent move for the Blue Jays to make, even if they had to pay a significant premium.
But, unfortunately, this whole situation isn’t as simple as ‘the insurance company is going to give the Blue Jays $20 million to compensate for Ryu so that financial commitment is off the books now!’ 
I spoke with a source familiar with sports contracts and insurance and they told me that payouts won’t start until a player has been on the Injured List for two months, so the Blue Jays likely won’t be getting insurance funds for the entirety of the $20 million Ryu is owed next season. Meanwhile, Ben Nicholson-Smith mentioned on Sportsnet recently that the claim can’t be filed until the contract is over, so the Blue Jays wouldn’t recoup any money until after the 2023 season.
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Also, as far as I know, Ryu’s salary would still be considered in luxury tax calculations, which are based on the average annual value of a contract, and the Blue Jays have indicated in the past that they aren’t going to be going over that threshold.
So, all things considered, don’t expect a $20 million spending spree this winter because of Ryu’s insurance money. This will add flexibility, for sure, but it might be more relevant come trade deadline time next summer rather than during the off-season.
Moving along…
The big story this winter in baseball is the free agency of Aaron Judge, who’s hitting the open market for the first time in his career following a season in which he hit 62 home runs and had a 1.111 OPS. But as good as Judge’s season was, it didn’t protect him from the harsh realities of being a Yankee when he went 1-for-16 in the American League Championship Series against the Houston Astros…
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“I’m an Astro, bro,” Reggie Jackson, a special advisor to Houston owner Jim Crane, told Mark Berman of Fox 26 last week at Minute Maid Park. “The pinstripes get heavy sometimes.”
It is not, therefore, a new emotion to be exhausted by the unrealistic expectations and anger that follows when those expectations aren’t met. Even Mr. October felt the weight of it. But even before the Astros swept the Yankees in the ALCS last weekend, the clubhouse and front office had quietly noticed that the external energy surrounding the team felt as angry as it has been in ages.
If you’re Aaron Judge, booed in the playoffs days after setting an American League home run record, why wouldn’t you prefer sunny Los Angeles or familiar San Francisco?”
“There appears to be some real concern within the Yankees’ ranks about their chances to keep Judge. The Yankees expect to be the high bidder – figure they’ll start just north of his original ask of $36 million a year. They just aren’t sure how badly he wants to stay.
Judge has never uttered a negative word about the Yankees but there was a clubhouse sense he had a bitter taste following spring negotiations. A source suggested he didn’t see why he should be below Anthony Rendon’s annual $35 million pay (as it turned out, he was right), and the $30.5 million a year offer seemed very light to him.”
The booing angle is probably sensationalized a bit. It’s a big thing in New York fandom, as fans are taught to cheer for things that are good and to boo things that are bad and that it isn’t really isn’t personal. If players can’t handle the booing, they won’t do well in such a market, and surely Judge is capable of brushing this off because it wasn’t the first time he had been booed.
But the other point is interesting. General manager Brian Cashman came out publicly right before the start of the season and said that the team offered Judge a seven-year contract worth $213.5 million, which is $30.5 million annually.
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If that offer seemed light in April, it’s hilariously low now given the season Judge just had. I doubt that Judge would scorn the Yankees entirely because of an offer he viewed to be light but all signs are pointing at the soon-to-be AL MVP not giving the Yankees any kind of hometown discount to stick around forever.
And given how New York’s spending has been trending in the years since George Steinbrenner passed away, it’s far from a guarantee that they’ll be the team that ultimately makes him the biggest offer…
Phillies in four! Let’s get Transaction Season started!!!

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