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At some point in the next three years Toronto Blue Jays wunderkind Vladimir Guerrero Jr. will either sign a possible record-setting contract extension to remain with the Blue Jays, or he'll become a free agent at age 26. Rarely does a player this good hit free agency that young. There was Bryce Harper and Manny Machado after the 2018 season. Before them, it was Alex Rodriguez in 2000.

We can already cross one team off the list of potential suitors should Guerrero hit free agency: the New York Yankees. During a recent interview with Vincent Carmona Arias, Vlad Jr. said he would never sign with New York.

"I like to play in New York. I like to kill the Yankees. I would never sign with the Yankees, not even (when I'm) dead," Guerrero said (translation via Z101 Digital's Héctor Gómez). 

For the record, Vlad Jr. is a career .289/.346/.518 hitter against the Yankees, including .289/.344/.579 with 10 homers in 31 games at Yankee Stadium. He had a three-homer game in the Bronx this April.

Of course, money has a way of changing minds, and Guerrero may rethink his position if the Yankees put $500 million on the table in three years. The Yankees have made a habit of passing on great free agents in recent years though. They didn't make much of an effort to sign Carlos Correa or Corey Seager last offseason, nor Harper or Machado four years ago. Declining to pursue Vlad Jr. when the time comes wouldn't be out of character.

Guerrero, 23, followed up his 2021 AL MVP runner-up season with a .274/.339/.480 line and 32 home runs in 2022. He also won a Gold Glove at first base. A year ago Vlad Jr. joined Hall of Famers Joe DiMaggio, Eddie Mathews, and Johnny Bench as the only players in history with a 45-homer season at age 22 or younger. There's a long way to go between now and free agency, but that's the trajectory Guerrero's on. Players who do what he's done tend to become all-time greats.

A few weeks ago Guerrero told Gómez he is open to signing a long-term extension with Toronto. "I feel really happy playing here. I hope something can be done about it this offseason," he added. Being open to a long-term deal and taking a discount are two very different things. The Yankees know that well after failing to lock up likely AL MVP and free agent-to-be Aaron Judge earlier this year.

Vlad Jr. will remain with the Blue Jays as an arbitration-eligible player through 2025. MLB Trade Rumors projects a $14.8 million salary in 2023 and their model has proven to be quite accurate over the years. Here are the largest extensions ever given to players three years away from free agency:

  1. Freddie Freeman, Braves: 8 years and $135 million
  2. Ryan Braun, Brewers: 6 years and $105 million with one option year
  3. Kyle Seager, Mariners: 7 years and $100 million with one option year
  4. Wil Myers, Padres: 6 years and $83 million with one option year
  5. Justin Morneau, Twins: 6 years and $80 million

The Myers contract is the most recent and he signed that deal in Jan. 2017, so while these are the benchmarks for players three years away from free agency, they are rather outdated. I am certain the Blue Jays would give Guerrero the Freeman extension tomorrow if he'd take it.

Keep in mind Guerrero is already making very good money through arbitration, and his father, Hall of Famer Vladimir Guerrero Sr., made over $125 million in his career. Life-changing money to Vlad Jr. is not the same as life-changing money to most players his age. He has leverage and can play hardball during extension talks because his family is already secure financially. 

Juan Soto is scheduled to become a free agent in two years, also at age 26. That's rather convenient for Guerrero. He can let Soto set the market for a 26-year-old superstar hitter before agreeing to an extension. Guerrero (and Soto) has to continue to perform for that plan to work, but that would be the way to go if his priority is signing the biggest deal possible.

It's also possible Guerrero says my family is already taken care of financially, so I don't need every last penny. I want to be happy and play for a winner. That kind of thing. At that point the sell job becomes more about the organization, and the Blue Jays have a great big head start on every other team. Vlad Jr. knows what they're about and how things run.

Either Guerrero will sign an extension with the Blue Jays or he'll become a free agent in three years. As he tells it, the Yankees will be a non-option should he hit the open market. He wants to beat the Yankees, not play for the Yankees.