<p>One of the biggest looming clouds hovering over the Toronto Blue Jays seems like it has dissipated. The &#8220;will they/won&#8217;t they&#8221; discourse surrounding the merits of trading Vladimir Guerrero Jr. and Bo Bichette has calmed down, for the time being.</p>
<p></p>
<p>With Vladdy, it&#8217;s because his recent hot streak may have priced him out for any would-be buyers on the market. Bichette&#8217;s offensive struggles have put him in a position where his value hasn&#8217;t been lower than it&#8217;s ever been, making it more advantageous to hang onto him for Toronto.</p>
<p>If the Blue Jays can sign Bo and Vlad on the dotted line for fair market value on a contract extension, that would be the best scenario. But there&#8217;s always a world where Toronto can only convince one to stay, and not the other.</p>
<p>With recency bias and 2024 production factoring in, the safer bet feels like for the Blue Jays to extend Guerrero Jr. But signing the face of your franchise to a massive contract extension comes with inherent risk on both sides; for the player and the team.</p>
<p>But with free agency looming, time is running out for the Blue Jays to decide on whether they want Vladdy to be part of the fabric of this club for the foreseeable future, or if they&#8217;re willing to move on from one of the most talented players from a raw skills standpoint that they&#8217;ve ever signed.</p>
<p>It&#8217;s not such a cut and dry decision for the Blue Jays, and an important decision which could have a monumental impact on the future of this franchise. Later this week, I&#8217;ll be diving into the pros of hanging onto Guerrero Jr., but for now, let&#8217;s hear what the devil on our shoulder has to say.</p>
<h2>The cons of a Vladdy extension</h2>
<p>Let&#8217;s start with negatives, because that&#8217;s where the chaotic fun lies. It&#8217;s hard to imagine Vladdy expecting anything less than a 10-year deal in the $300-$350 million stratosphere, just for argument&#8217;s sake. That&#8217;s a tonne of money for a player has one great season under his belt through his first six seasons in the big leagues.</p>
<p>I can&#8217;t think of a player with more variance in that short of a span than Vlad himself. To go from the consensus number one prospect, to the worst fielding third baseman in baseball, to one of the best hitters in the league, to a good hitter, to a slightly-better-than-league-average hitter is quite the journey.</p>
<h2>His uneven track record</h2>
<p>Projections always seem to love Guerrero, but the eye test over the last few years has not matched the vaulted expectations for a player of his calibre. He&#8217;s performed more like a secondary cast member rather than &#8220;the guy&#8221; the last few seasons, and you don&#8217;t lock up the supporting players, you lock up &#8220;the guy.&#8221;</p>
<p>He&#8217;s only 25 years old now and may head into his age-27 season as a free agent, which is quite young in terms of players entering the free agent pool. But when hundreds of millions of dollars are on the line, judge a player like him on his seasons in the past, not the potential ahead.</p>
<p>Let&#8217;s also recognize that at his young age, Vlad&#8217;s already transitioned over to first base, sometimes a spot reserved for big contract players in the twilight of their career, not their prime. This also has a huge bearing on the potential contract out there for Vlad, and the comps aren&#8217;t so cut and dry.</p>
<p>Players like Bryce Harper and Kris Bryant transitioned over to first base after signing their big deals, so their omission from this list was intentional. So here are the most recent comps for free agent first baseman contracts and contract extensions.</p>
<h2>The first baseman deal comps</h2>
<table width="442">
<tbody>
<tr>
<td style="text-align: center;" width="122"><strong>Player</strong></td>
<td style="text-align: center;" width="64"><strong>Term</strong></td>
<td style="text-align: center;" width="64"><strong>Dollars</strong></td>
<td style="text-align: center;" width="64"><strong>AAV</strong></td>
<td style="text-align: center;" width="64"><strong>Age</strong></td>
<td style="text-align: center;" width="64"><strong>Year</strong></td>
</tr>
<tr>
<td style="text-align: center;">Jake Cronenworth</td>
<td style="text-align: center;">7 years</td>
<td style="text-align: center;">$80M</td>
<td style="text-align: center;">$11.4M</td>
<td style="text-align: center;">29</td>
<td style="text-align: center;">2023</td>
</tr>
<tr>
<td style="text-align: center;">Matt Olson</td>
<td style="text-align: center;">8 years</td>
<td style="text-align: center;">$168M</td>
<td style="text-align: center;">$21M</td>
<td style="text-align: center;">28</td>
<td style="text-align: center;">2022</td>
</tr>
<tr>
<td style="text-align: center;">Freddie Freeman</td>
<td style="text-align: center;">6 years</td>
<td style="text-align: center;">$162M</td>
<td style="text-align: center;">$27M</td>
<td style="text-align: center;">32</td>
<td style="text-align: center;">2022</td>
</tr>
<tr>
<td style="text-align: center;">Paul Goldschmidt</td>
<td style="text-align: center;">5 years</td>
<td style="text-align: center;">$130M</td>
<td style="text-align: center;">$26M</td>
<td style="text-align: center;">31</td>
<td style="text-align: center;">2019</td>
</tr>
<tr>
<td style="text-align: center;">Joey Votto</td>
<td style="text-align: center;">10 years</td>
<td style="text-align: center;">$225M</td>
<td style="text-align: center;">$22.5M</td>
<td style="text-align: center;">28</td>
<td style="text-align: center;">2012</td>
</tr>
</tbody>
</table>
<p>It&#8217;s not apples to apples, but the Matt Olson and Freddie Freeman deals might be the most realistic comparables to what a player of Vladdy&#8217;s calibre might fetch in free agency. In reality, that Joey Votto extension from 2012 might be what Guerrero&#8217;s camp is looking for.</p>
<p>But at a similar AAV of $22.5 million, that’s slightly more than the $19.5 million he earned in arbitration this year, with something in the neighbourhood of $24-$25 million coming his way in his final year of arbitration, anything under the $30 million AAV seems low.</p>
<p>Unless Guerrero will take a haircut (he already did, ha!) in term and go seven years at $30 million for $210 million total, an extreme hometown discount for the Blue Jays will not be happening.</p>
<p>And from a business perspective, is this the player you want to hang your hat on? Do the Blue Jays believe Guerrero Jr. will be integral in leading them to the promised land? With his track record over the last few seasons, I&#8217;m not so sure he&#8217;s the anchor on this roster.</p>
<h2>Better to spend big on Soto instead?</h2>
<p>There is another player out there who would be tempting to anoint as an anchor, who would cost significantly more, but would be worth every penny. Juan Soto is the same age, and has four five-plus fWAR seasons under his belt (this season included), while Vladdy has one.</p>
<p>The Soto/Guerrero comp is low-hanging fruit, but in some respects they&#8217;re viewed as players in the same echelon, but Soto is in a higher class than Guerrero. And when Soto commands $400-$500 million this winter, he&#8217;ll have earned every penny.</p>
<p>Soto is hitting the market at the most opportune time, while if the Blue Jays were to throw a boatload of money at Guerrero, it might be a case where the Blue Jays are signing him in fear of letting him go, rather than making the right bet.</p>
<h2>Avoiding a Vernon Wells 2.0 fiasco</h2>
<p>The obvious comp where things have the potential to go sideways was the Vernon Wells extension, which felt like an overpay the instant that seven-year/$126 million deal was finalized. The Blue Jays were lucky to get out from under the contract, but if they go big dollars and went long-term with Guerrero, they might not get so lucky in the back end of a potential deal.</p>
<p>It’s common for the Blue Jays to overpay in term or dollars to lure free agents, but that doesn&#8217;t mean overpaying to secure another guy you&#8217;re afraid to see play for the Yankees or Red Sox.</p>
<h2>Not just a Vladdy away</h2>
<p>Inking Guerrero as a long-time Blue Jay would be a tidy piece of business for this front office, but it&#8217;s securing one player on the 26-man roster when this club is much further than a Vladdy away from contending over the next two to three years.</p>
<p>Instead of just one position, the team has the option to spend a salary earmarked for Guerrero at several positions. The Blue Jays have a bulk of their roster hitting free agency over the next few seasons, with multiple core positions to fill.</p>
<p>First baseman of Guerrero&#8217;s calibre aren&#8217;t a dime a dozen, but regular first baseman are. If you figure Vlad fetches a $30 million or more AAV, Toronto could sign two or three players for the same amount.</p>
<h2>In conclusion &#8230;</h2>
<p>The talent of Guerrero is undeniable. His family&#8217;s gene pool is rife with big league experience. He has natural gifts that most players can only dream of having in their toolbox. But at some point, you have to know when to walk away from the blackjack table.</p>
<p>Since his breakout 2021 campaign, there are more questions now than ever about what to expect out of Vladdy. Making that gamble with hundreds of millions of dollars on the line for the fifth-best first baseman in MLB right now is a risky proposition.</p>
<p>You can hope and pray that he somehow unlocks that magic from his 2021 season, but we&#8217;re almost three years removed from that campaign, with diminishing results every year after. He might be a generational talent, but he&#8217;s not the <em>last</em> generational talent.</p>
<p><em>Coming up tomorrow &#8230; the inverse of this argument: Why the Blue Jays should go all-in with a Guerrero extension</em></p>

One of the biggest looming clouds hovering over the Toronto Blue Jays seems like it has dissipated. The "will they/won't they" discourse surrounding the merits of trading Vladimir Guerrero Jr. and Bo Bichette has calmed down, for the time being.



With Vladdy, it's because his recent hot streak may have priced him out for any would-be buyers on the market. Bichette's offensive struggles have put him in a position where his value hasn't been lower than it's ever been, making it more advantageous to hang onto him for Toronto.

If the Blue Jays can sign Bo and Vlad on the dotted line for fair market value on a contract extension, that would be the best scenario. But there's always a world where Toronto can only convince one to stay, and not the other.

With recency bias and 2024 production factoring in, the safer bet feels like for the Blue Jays to extend Guerrero Jr. But signing the face of your franchise to a massive contract extension comes with inherent risk on both sides; for the player and the team.

But with free agency looming, time is running out for the Blue Jays to decide on whether they want Vladdy to be part of the fabric of this club for the foreseeable future, or if they're willing to move on from one of the most talented players from a raw skills standpoint that they've ever signed.

It's not such a cut and dry decision for the Blue Jays, and an important decision which could have a monumental impact on the future of this franchise. Later this week, I'll be diving into the pros of hanging onto Guerrero Jr., but for now, let's hear what the devil on our shoulder has to say.
<h2>The cons of a Vladdy extension</h2>
Let's start with negatives, because that's where the chaotic fun lies. It's hard to imagine Vladdy expecting anything less than a 10-year deal in the $300-$350 million stratosphere, just for argument's sake. That's a tonne of money for a player has one great season under his belt through his first six seasons in the big leagues.

I can't think of a player with more variance in that short of a span than Vlad himself. To go from the consensus number one prospect, to the worst fielding third baseman in baseball, to one of the best hitters in the league, to a good hitter, to a slightly-better-than-league-average hitter is quite the journey.
<h2>His uneven track record</h2>
Projections always seem to love Guerrero, but the eye test over the last few years has not matched the vaulted expectations for a player of his calibre. He's performed more like a secondary cast member rather than "the guy" the last few seasons, and you don't lock up the supporting players, you lock up "the guy."

He's only 25 years old now and may head into his age-27 season as a free agent, which is quite young in terms of players entering the free agent pool. But when hundreds of millions of dollars are on the line, judge a player like him on his seasons in the past, not the potential ahead.

Let's also recognize that at his young age, Vlad's already transitioned over to first base, sometimes a spot reserved for big contract players in the twilight of their career, not their prime. This also has a huge bearing on the potential contract out there for Vlad, and the comps aren't so cut and dry.

Players like Bryce Harper and Kris Bryant transitioned over to first base after signing their big deals, so their omission from this list was intentional. So here are the most recent comps for free agent first baseman contracts and contract extensions.
<h2>The first baseman deal comps</h2>
<table width="442">
<tbody>
<tr>
<td style="text-align: center;" width="122"><strong>Player</strong></td>
<td style="text-align: center;" width="64"><strong>Term</strong></td>
<td style="text-align: center;" width="64"><strong>Dollars</strong></td>
<td style="text-align: center;" width="64"><strong>AAV</strong></td>
<td style="text-align: center;" width="64"><strong>Age</strong></td>
<td style="text-align: center;" width="64"><strong>Year</strong></td>
</tr>
<tr>
<td style="text-align: center;">Jake Cronenworth</td>
<td style="text-align: center;">7 years</td>
<td style="text-align: center;">$80M</td>
<td style="text-align: center;">$11.4M</td>
<td style="text-align: center;">29</td>
<td style="text-align: center;">2023</td>
</tr>
<tr>
<td style="text-align: center;">Matt Olson</td>
<td style="text-align: center;">8 years</td>
<td style="text-align: center;">$168M</td>
<td style="text-align: center;">$21M</td>
<td style="text-align: center;">28</td>
<td style="text-align: center;">2022</td>
</tr>
<tr>
<td style="text-align: center;">Freddie Freeman</td>
<td style="text-align: center;">6 years</td>
<td style="text-align: center;">$162M</td>
<td style="text-align: center;">$27M</td>
<td style="text-align: center;">32</td>
<td style="text-align: center;">2022</td>
</tr>
<tr>
<td style="text-align: center;">Paul Goldschmidt</td>
<td style="text-align: center;">5 years</td>
<td style="text-align: center;">$130M</td>
<td style="text-align: center;">$26M</td>
<td style="text-align: center;">31</td>
<td style="text-align: center;">2019</td>
</tr>
<tr>
<td style="text-align: center;">Joey Votto</td>
<td style="text-align: center;">10 years</td>
<td style="text-align: center;">$225M</td>
<td style="text-align: center;">$22.5M</td>
<td style="text-align: center;">28</td>
<td style="text-align: center;">2012</td>
</tr>
</tbody>
</table>
It's not apples to apples, but the Matt Olson and Freddie Freeman deals might be the most realistic comparables to what a player of Vladdy's calibre might fetch in free agency. In reality, that Joey Votto extension from 2012 might be what Guerrero's camp is looking for.

But at a similar AAV of $22.5 million, that’s slightly more than the $19.5 million he earned in arbitration this year, with something in the neighbourhood of $24-$25 million coming his way in his final year of arbitration, anything under the $30 million AAV seems low.

Unless Guerrero will take a haircut (he already did, ha!) in term and go seven years at $30 million for $210 million total, an extreme hometown discount for the Blue Jays will not be happening.

And from a business perspective, is this the player you want to hang your hat on? Do the Blue Jays believe Guerrero Jr. will be integral in leading them to the promised land? With his track record over the last few seasons, I'm not so sure he's the anchor on this roster.
<h2>Better to spend big on Soto instead?</h2>
There is another player out there who would be tempting to anoint as an anchor, who would cost significantly more, but would be worth every penny. Juan Soto is the same age, and has four five-plus fWAR seasons under his belt (this season included), while Vladdy has one.

The Soto/Guerrero comp is low-hanging fruit, but in some respects they're viewed as players in the same echelon, but Soto is in a higher class than Guerrero. And when Soto commands $400-$500 million this winter, he'll have earned every penny.

Soto is hitting the market at the most opportune time, while if the Blue Jays were to throw a boatload of money at Guerrero, it might be a case where the Blue Jays are signing him in fear of letting him go, rather than making the right bet.
<h2>Avoiding a Vernon Wells 2.0 fiasco</h2>
The obvious comp where things have the potential to go sideways was the Vernon Wells extension, which felt like an overpay the instant that seven-year/$126 million deal was finalized. The Blue Jays were lucky to get out from under the contract, but if they go big dollars and went long-term with Guerrero, they might not get so lucky in the back end of a potential deal.

It’s common for the Blue Jays to overpay in term or dollars to lure free agents, but that doesn't mean overpaying to secure another guy you're afraid to see play for the Yankees or Red Sox.
<h2>Not just a Vladdy away</h2>
Inking Guerrero as a long-time Blue Jay would be a tidy piece of business for this front office, but it's securing one player on the 26-man roster when this club is much further than a Vladdy away from contending over the next two to three years.

Instead of just one position, the team has the option to spend a salary earmarked for Guerrero at several positions. The Blue Jays have a bulk of their roster hitting free agency over the next few seasons, with multiple core positions to fill.

First baseman of Guerrero's calibre aren't a dime a dozen, but regular first baseman are. If you figure Vlad fetches a $30 million or more AAV, Toronto could sign two or three players for the same amount.
<h2>In conclusion ...</h2>
The talent of Guerrero is undeniable. His family's gene pool is rife with big league experience. He has natural gifts that most players can only dream of having in their toolbox. But at some point, you have to know when to walk away from the blackjack table.

Since his breakout 2021 campaign, there are more questions now than ever about what to expect out of Vladdy. Making that gamble with hundreds of millions of dollars on the line for the fifth-best first baseman in MLB right now is a risky proposition.

You can hope and pray that he somehow unlocks that magic from his 2021 season, but we're almost three years removed from that campaign, with diminishing results every year after. He might be a generational talent, but he's not the <em>last</em> generational talent.

<em>Coming up tomorrow ... the inverse of this argument: Why the Blue Jays should go all-in with a Guerrero extension</em>

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