Article: Even Alex Anthopoulos Wouldn’t Have Extended Vladimir Guerrero Jr.

[Davy Andrews]

Vladimir Guerrero Jr. is a very different player, in a very different situation, than the many players Anthopoulos has locked down to contract extensions.

On Sunday, Mike Wilner, baseball columnist at the Toronto Star, published an opinion piece titled “Blue Jays fans know Vladimir Guerrero Jr. would likely be staying if Alex Anthopoulos didn’t go,” and, well, the title pretty much says it all. Like so many Blue Jays fans, Wilner is understandably disheartened by the team’s failure to lock up young stars Guerrero and Bo Bichette. He’s watching Anthopolous build a juggernaut through long-term contract extensions and wishing that could have happened in Toronto. However, I disagree pretty strongly with Wilner’s central premise, and I thought it might be helpful to lay out my reasoning.

Let’s start with where I agree with Wilner. First, obviously, anyone who loves the Blue Jays wants to see Guerrero and Bichette wearing blue forever. It would be good for the team and good for baseball. And I don’t think anyone can argue the point that the current front office led by Mark Shapiro and Ross Atkins has at times made it discouraging to be a fan. No one actually knows what goes on in the room during negotiations, but the team has earned a reputation for coming to its own determination about the value of a player, and sticking to it no matter what. That can help a team avoid disastrous moves, but it can also make them whiff on a lot of impact players. Andrew Freidman famously said, “If you’re always rational about every free agent, you will finish third on every free agent,” and lately, no team has finished third more often than the Blue Jays.

That said, it’s not as if the Blue Jays aren’t trying. According to Cot’s Contracts, they’ve run top-10 payrolls in each of the last two seasons, and they rank fifth for 2025, as things stand now. They’re committed to winning, and they’re putting their money where their mouth is. Although they haven’t won a playoff game in years, they’ve made it there in two of the last three seasons while playing in the toughest division in baseball, and it’s hard to ding them too much for the randomness of the postseason.

My bigger issue with the piece is that it lacks some crucial context about the players that Anthopoulos has targeted. Over the past seven years, he’s locked in long-term extensions to Ronald Acuña Jr., Ozzie Albies, Austin Riley, Sean Murphy, Matt Olson, Michael Harris II, and Spencer Strider. That’s a whole lot of stars, and many of them were signed for well below market value. That’s not an accident. The Braves have targeted extensions for players and agents who were not in a position to negotiate for the best deal possible. So many star players pick big, powerful agencies like Boras Corp and CAA for a reason. They’ve got experience and resources that give them leverage to fight for the best deal possible, even if it means waiting for years until their clients hit free agency.

Acuña and Albies were represented by small agencies for whom an early extension, even one that was dramatically under market value, meant a huge increase in revenue. Sure, Acuña and Albies signed deals that gave them generational wealth, but they were still staggering, arguably unethical underpays of young players who got signing bonuses as teenagers and then made virtually nothing for years as they worked their way through the minors. Those deals prompted headlines like “Ronald Acuña changes agents years after signing insane team-friendly contract” and “Here’s Why the Ozzie Albies Deal Was Terrible” and “What Can the MLBPA Do About Ozzie Albies’ Deal?”. I’m not asking you to feel sorry for Albies and Acuña. They have almost certainly made more money than everyone who will read this article put together. However, if I were a fan of the Braves, I don’t know that I’d feel great about these deals.

Bichette and Guerrero are not in the same position at all. They’re the sons of two major leaguers who made plenty of money in their day. They’re not desperate and their agencies aren’t desperate either. Bichette is represented by Vayner Sports and is a former client of CAA, two major agencies. Guerrero is represented by Magnus Sports, a smaller agency, but one owned by a celebrity trying to make a major impact in the game. These are two players who were never in a million years going to sign deals like the ones Albies and Acuña signed. The Blue Jays did a great job of picking and developing them, and they’ve reaped tons of value from it. It’s not the team’s fault Guerrero and Bichette have more options available to them than Acuña and Albies did, and it would have been absurd for them to avoid signing or drafting them on that basis.

A more apt comp for Guerrero would be Freddie Freeman. The first baseman was a star with the Braves for 10 years and was all but certain to end up with a cursive A on his hat in Cooperstown. He had already signed one deal to stay in Atlanta, in 2014, before Anthopoulos’s tenure. It was an eight-year deal that bought out his final two years of arbitration, meaning that it extended him for six years. To be clear, there’s no way Guerrero would have signed a deal like that. When that extension was was up, the Braves decided to get younger, waving goodbye to Freeman without a second thought. They traded for Matt Olson and signed him to an extension that was similar to Freeman’s deal with the Dodgers in terms of dollars, but included two extra years. Like Olson, Murphy is represented by a smaller agency, arrived in Atlanta via trade, and was promptly locked into a contract extension. This is a pattern, and a clever one: targeting players with agents who might be more likely to play ball on extensions. Wilner is right to recognize that Anthopoulos has exploited this particular inefficiency and to wish that the Blue Jays had found their own secret sauce.

However, let's get back to Freeman and Olson. Starting in 2022, Freeman has put up 18.7 fWAR to Olson’s 12.2, and he just won World Series MVP. Now, as I mentioned, Olson is five years younger, so his deal way end up looking better in the long run, but I think there are some real parallels here. This was a future Hall of Fame first baseman looking to get paid what he deserved his first free agent contract, and Anthopoulos wanted nothing to do with that. Say what you will about the Blue Jays’ efforts, but there’s no doubt that they did make genuine offers to Guerrero.

So that’s my main argument. I’m don’t mean to drag Wilner at all, and I don’t think you can fault anyone for looking at what’s happening in Atlanta and wishing that it were happening in Toronto. I just didn’t think he was quite comparing apples to apples, so I wanted to take a more nuanced look.

I’d also remind you that long-term extensions can have downsides. I’m a big fan of them, especially when they seem to have a fair proportion of risk to certainty. A young player with potential Jackson Chourio or Julio Rodriguez gets big money before they’re a sure thing, and the team gets a bargain because they’re taking a chance. There’s a fairness there. But still, not every extension is going to work out, and not all will be slam dunks like Acuña’s and Albies’. Strider, Acuña, and Albies have all been fantastic, but have also missed significant time to injuries. Riley, Olson, Harris, and Murphy all took major steps back in 2024. I think most of them will bounce back to play well in the future, but that’s part of the deal when it comes to long-term extensions. You end up taking the good with the bad. There was a time when the Blue Jays would have looked like prophets for locking up Alek Manoah to a shiny 10-year deal. We would have been singing the praises of Shapiro and Atkins for two seasons, and then we would have spent the last two seasons – and maybe the next six! – tearing our hair out and complaining about how the deal was hamstringing the team. My point is that these things are complicated. We won’t know for many years how the careers of Guerrero or Bichette turn out. For now, I guess we should just enjoy them while we can.

 

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[Stangstag]

Finally someone rational about the Vlad situation

[Brock Beauchamp]

I like the comp to Freeman for Vlad. It's a much better comparison than Acuna, Albies, etc.

And I think it's often overlooked that both Vlad and Bichette come from generational wealth. That surely gives them a perspective and patience that most other players, particularly Latin players, can't afford to have.

[glory]

3 hours ago, Stangstag said:

Finally someone rational about the Vlad situation

Yeah AA does not pay market value with extensions. He tries to get the team friendliest deals he can get, and to his credit he gets a bunch of them done, but Vlad has wanted $300M+ at least since 2021 when Tatis signed his deal. There was never going to be a team friendly discount even if AA was the GM.

[BatFlip]

"Bichette and Guerrero are not in the same position at all. They’re the sons of two major leaguers who made plenty of money in their day. They’re not desperate and their agencies aren’t desperate either. Bichette is represented by Vayner Sports and is a former client of CAA, two major agencies. Guerrero is represented by Magnus Sports, a smaller agency, but one owned by a celebrity trying to make a major impact in the game. These are two players who were never in a million years going to sign deals like the ones Albies and Acuña signed."

[Spanky99]

Great read, bang on.

[GNick92]

22 hours ago, Davy Andrews said:

Vladimir Guerrero Jr. is a very different player, in a very different situation, than the many players Anthopoulos has locked down to contract extensions.

On Sunday, Mike Wilner, baseball columnist at the Toronto Star, published an opinion piece titled “Blue Jays fans know Vladimir Guerrero Jr. would likely be staying if Alex Anthopoulos didn’t go,” and, well, the title pretty much says it all. Like so many Blue Jays fans, Wilner is understandably disheartened by the team’s failure to lock up young stars Guerrero and Bo Bichette. He’s watching Anthopolous build a juggernaut through long-term contract extensions and wishing that could have happened in Toronto. However, I disagree pretty strongly with Wilner’s central premise, and I thought it might be helpful to lay out my reasoning.

Let’s start with where I agree with Wilner. First, obviously, anyone who loves the Blue Jays wants to see Guerrero and Bichette wearing blue forever. It would be good for the team and good for baseball. And I don’t think anyone can argue the point that the current front office led by Mark Shapiro and Ross Atkins has at times made it discouraging to be a fan. No one actually knows what goes on in the room during negotiations, but the team has earned a reputation for coming to its own determination about the value of a player, and sticking to it no matter what. That can help a team avoid disastrous moves, but it can also make them whiff on a lot of impact players. Andrew Freidman famously said, “If you’re always rational about every free agent, you will finish third on every free agent,” and lately, no team has finished third more often than the Blue Jays.

That said, it’s not as if the Blue Jays aren’t trying. According to Cot’s Contracts, they’ve run top-10 payrolls in each of the last two seasons, and they rank fifth for 2025, as things stand now. They’re committed to winning, and they’re putting their money where their mouth is. Although they haven’t won a playoff game in years, they’ve made it there in two of the last three seasons while playing in the toughest division in baseball, and it’s hard to ding them too much for the randomness of the postseason.

My bigger issue with the piece is that it lacks some crucial context about the players that Anthopoulos has targeted. Over the past seven years, he’s locked in long-term extensions to Ronald Acuña Jr., Ozzie Albies, Austin Riley, Sean Murphy, Matt Olson, Michael Harris II, and Spencer Strider. That’s a whole lot of stars, and many of them were signed for well below market value. That’s not an accident. The Braves have targeted extensions for players and agents who were not in a position to negotiate for the best deal possible. So many star players pick big, powerful agencies like Boras Corp and CAA for a reason. They’ve got experience and resources that give them leverage to fight for the best deal possible, even if it means waiting for years until their clients hit free agency.

Acuña and Albies were represented by small agencies for whom an early extension, even one that was dramatically under market value, meant a huge increase in revenue. Sure, Acuña and Albies signed deals that gave them generational wealth, but they were still staggering, arguably unethical underpays of young players who got signing bonuses as teenagers and then made virtually nothing for years as they worked their way through the minors. Those deals prompted headlines like “Ronald Acuña changes agents years after signing insane team-friendly contract” and “Here’s Why the Ozzie Albies Deal Was Terrible” and “What Can the MLBPA Do About Ozzie Albies’ Deal?”. I’m not asking you to feel sorry for Albies and Acuña. They have almost certainly made more money than everyone who will read this article put together. However, if I were a fan of the Braves, I don’t know that I’d feel great about these deals.

Bichette and Guerrero are not in the same position at all. They’re the sons of two major leaguers who made plenty of money in their day. They’re not desperate and their agencies aren’t desperate either. Bichette is represented by Vayner Sports and is a former client of CAA, two major agencies. Guerrero is represented by Magnus Sports, a smaller agency, but one owned by a celebrity trying to make a major impact in the game. These are two players who were never in a million years going to sign deals like the ones Albies and Acuña signed. The Blue Jays did a great job of picking and developing them, and they’ve reaped tons of value from it. It’s not the team’s fault Guerrero and Bichette have more options available to them than Acuña and Albies did, and it would have been absurd for them to avoid signing or drafting them on that basis.

A more apt comp for Guerrero would be Freddie Freeman. The first baseman was a star with the Braves for 10 years and was all but certain to end up with a cursive A on his hat in Cooperstown. He had already signed one deal to stay in Atlanta, in 2014, before Anthopoulos’s tenure. It was an eight-year deal that bought out his final two years of arbitration, meaning that it extended him for six years. To be clear, there’s no way Guerrero would have signed a deal like that. When that extension was was up, the Braves decided to get younger, waving goodbye to Freeman without a second thought. They traded for Matt Olson and signed him to an extension that was similar to Freeman’s deal with the Dodgers in terms of dollars, but included two extra years. Like Olson, Murphy is represented by a smaller agency, arrived in Atlanta via trade, and was promptly locked into a contract extension. This is a pattern, and a clever one: targeting players with agents who might be more likely to play ball on extensions. Wilner is right to recognize that Anthopoulos has exploited this particular inefficiency and to wish that the Blue Jays had found their own secret sauce.

However, let's get back to Freeman and Olson. Starting in 2022, Freeman has put up 18.7 fWAR to Olson’s 12.2, and he just won World Series MVP. Now, as I mentioned, Olson is five years younger, so his deal way end up looking better in the long run, but I think there are some real parallels here. This was a future Hall of Fame first baseman looking to get paid what he deserved his first free agent contract, and Anthopoulos wanted nothing to do with that. Say what you will about the Blue Jays’ efforts, but there’s no doubt that they did make genuine offers to Guerrero.

So that’s my main argument. I’m don’t mean to drag Wilner at all, and I don’t think you can fault anyone for looking at what’s happening in Atlanta and wishing that it were happening in Toronto. I just didn’t think he was quite comparing apples to apples, so I wanted to take a more nuanced look.

I’d also remind you that long-term extensions can have downsides. I’m a big fan of them, especially when they seem to have a fair proportion of risk to certainty. A young player with potential Jackson Chourio or Julio Rodriguez gets big money before they’re a sure thing, and the team gets a bargain because they’re taking a chance. There’s a fairness there. But still, not every extension is going to work out, and not all will be slam dunks like Acuña’s and Albies’. Strider, Acuña, and Albies have all been fantastic, but have also missed significant time to injuries. Riley, Olson, Harris, and Murphy all took major steps back in 2024. I think most of them will bounce back to play well in the future, but that’s part of the deal when it comes to long-term extensions. You end up taking the good with the bad. There was a time when the Blue Jays would have looked like prophets for locking up Alek Manoah to a shiny 10-year deal. We would have been singing the praises of Shapiro and Atkins for two seasons, and then we would have spent the last two seasons – and maybe the next six! – tearing our hair out and complaining about how the deal was hamstringing the team. My point is that these things are complicated. We won’t know for many years how the careers of Guerrero or Bichette turn out. For now, I guess we should just enjoy them while we can.

 

 

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Anthopoulos locked up Romero and it was a disaster 

[BB17]

On 3/5/2025 at 8:32 AM, Brock Beauchamp said:

I like the comp to Freeman for Vlad. It's a much better comparison than Acuna, Albies, etc.

And I think it's often overlooked that both Vlad and Bichette come from generational wealth. That surely gives them a perspective and patience that most other players, particularly Latin players, can't afford to have.

I would hardly call Bichette from generational wealth. His dad made like 40M in his career which Bo has made himself before even reaching FA. When you figure taxes and fees take probably half of that there is a lot less than you think.

Theres lots of kids coming out of the draft these days whos parents have just as much money. The reality is baseball is super expensive to play now a days so most of these kids on the travel teams come from wealthy families. Obviously the latin americans are different but I'm talking from a Canada/US perspective.

[John_Havok]

3 minutes ago, BB17 said:

I would hardly call Bichette from generational wealth. His dad made like 40M in his career which Bo has made himself before even reaching FA. When you figure taxes and fees take probably half of that there is a lot less than you think.

Theres lots of kids coming out of the draft these days whos parents have just as much money. The reality is baseball is super expensive to play now a days so most of these kids on the travel teams come from wealthy families. Obviously the latin americans are different but I'm talking from a Canada/US perspective.

If you think Bo didn't come from generational wealth, I'm not sure what you think generational wealth is, or your bar for it is REALLY high

[BB17]

4 hours ago, John_Havok said:

If you think Bo didn't come from generational wealth, I'm not sure what you think generational wealth is, or your bar for it is REALLY high

My definition would be that your grandkids would never have to work/worry about money but I guess it is very subjective person to person. 

What I was trying to say more though is that a lot of the best kids coming out of the draft these days are coming from wealthy families with 8 figure net worths. To play the highest level youth baseball the costs are 10-20K a year not even including all the travel costs for the families so most of the kids have to come from money. Hockey is the same way, guys like Marner and Hyman came from families with tons of $.

Kids who don't come from money usually end up playing basketball or football because they can play for the high school and go to college from there.