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Since being promoted to President of Baseball Operations in 2021, AJ Preller has shelled out some hefty contracts. The San Diego Padres have a 2025 payroll of almost $210 million, making them the ninth most expensive roster in Major League Baseball.

The team is spending more than $104 million on five players this season. Those players are Manny Machado, Fernando Tatis Jr., Xander Bogaerts, Yu Darvish, and Joe Musgrove. Jackson Merrill is also signed long-term with the Padres, but he is omitted here because his contract extension has not yet taken effect.

The contracts each player signed are for many years, with pretty sizable AAVs. The significant financial commitment makes playing the long-term extension game very risky, and the numbers suggest that Preller has had both wins and losses.

Preller signed Machado to a contract extension before the 2023 season for 11 years and $350 million, keeping Machado in San Diego through 2033. Machado’s deal has an AAV of $31.8 million. 

Since signing the extension, Machado has been very solid both offensively and defensively. Since 2023, he has appeared in 369 games, hit for an average of .274 with 72 home runs, and 243 RBI, good for an OPS of .806, an OPS+ of 121, and 8.5 WAR. Machado’s defense has saved the Padres 7 runs.

Machado’s contract looks great when you compare it to that of Nolan Arenado. The St. Louis Cardinals have Arenado on a contract with an AAV of $32.5 million. 

In the time since Machado’s extension, Arenado has played in 370 games and compiled 5.9 WAR. He has been significantly less productive than Machado at the plate, posting significantly worse numbers across the board. Arenado’s defense has been the saving grace of his contract, playing third base well enough to save his team 12 runs.

When compared to the $20.1 million AAV of Cleveland Guardians third baseman José Ramirez’s contract, Machado’s contract looks less like a deal. However, it should be noted that Ramirez took a very team-friendly deal to remain in Cleveland.

Since 2023, Ramirez has outperformed Machado at the plate in almost every area, with Machado only having more RBI, while playing defense good enough to have the same DRS as Machado at 7. In 389 games since 2023, Ramirez has posted an average of .287, hitting 76 home runs, driving in 234 runs, playing to an OPS of .860, an OPS+ of 138, and 14.7 WAR.

How Machado ages into his mid-to-late 30s remains to be seen, but as of now, about two and a half years into his extension, his contract appears to be of at least acceptable value.

Preller gave a contract of similar value to Fernando Tatis Jr. before the 2021 season. On February 17th, 2021, Tatis Jr. signed a 14-year contract worth $340 million. The contract has an AAV of $24.4 million.

Since signing the deal, Tatis Jr. has been one of the best players in all of baseball. He has been a stud, playing to an OPS of 847 and an OPS+ of 132. In 451 games since signing the new contract, he has put up a batting average of .269, mashing 103 home runs, and batting in 261 runs, good for 18.1 WAR.

Tatis Jr.’s game is more than just his bat; he has also been very good on defense. He has posted a DRS score of 32 since being extended.

The contract Tatis Jr. signed has an AAV slightly less than that of Toronto Blue Jays right fielder George Springer, at $25 million. Since 2021, Tatis Jr. has outperformed Springer in virtually all categories at the plate. Springer has more hits and RBIs, but Tatis Jr. has put up considerably higher marks in WAR, OPS, and OPS+. Springer also signed with Toronto as a free agent, whereas Tatis's extension also covers his lower-paying arbitration seasons.

A player with a contract that makes the Tatis Jr. contract look like an overpay is Ronald Acuna Jr. of the Atlanta Braves. Acuna has a contract with an AAV of $12.5 million. Since the 2021 season, Acuna Jr. has posted a batting average of .301 with 93 home runs and 241 runs batted in. He has posted 16.4 WAR, an OPS of .918, and an OPS+ of 149.

There have been rumblings recently about Acuna Jr. receiving a restructured deal that would give him an AAV of up to $25 million. Take that into consideration, and the Tatis Jr. deal looks a lot less like an overpay and more like the team is paying a reasonable price for him.

The long-term contract game is a dangerous one, and while Preller has looked relatively solid so far, he has been torched by one of his long-term contracts.

On December 9, 2022, Preller closed a deal that landed shortstop Xander Bogaerts in San Diego for 11 years and $280 million. In the two and change seasons Bogaerts has spent in a Padres uniform, he has played in 344 games, hitting for an average of .270 with 34 home runs while driving in 131 runs. His production under the contract he signed has been subpar so far, with 6.2 WAR, an OPS of .731, and an OPS+ of 102.

Looking at the numbers, Bogaerts’ production doesn’t look horrible at all. Consider that his contract has an AAV of $25.4 million, an average production of roughly three wins per season, and things start to change. An MLB "win" (based on the metric WAR) is usually worth approximately $8-9 million per season. Bogaerts has slightly underperformed in the first 2.5 years of his contract, which does not bode well for a deal that pays the shortstop through the 2033 season.

Joe Musgrove and Yu Darvish are on smaller contracts with the team, but have not been healthy enough to play enough games to assess how Preller did on their contracts. Both contracts began before the 2023 season.

Darvish has played in 40 games since signing his 6-year $108 million contract, and Musgrove has played in 36 since receiving his 5-year $100 million contract. Darvish has pitched to a 4.09 ERA over 218 innings, while Musgrove has a 3.47 ERA over 197 innings.

Logan Webb of the San Francisco Giants and Kodai Senga of the New York Mets are pitchers with similar AAV contracts, and both are outperforming Darvish and Musgrove in ERA and WAR over more innings pitched.

Injuries are impossible to predict, so dogging Preller for giving Musgrove and Darvish those contracts is a little difficult to do, especially when both put up very respectable strikeout and walk percentages when pitching.

From the look of it right now, Preller’s decision-making on dishing out long-term contracts has been relatively solid, especially on the Machado and Tatis Jr. deals. The Musgrove and Darvish deals appear to be decent values if they can stay healthy. The baseball world may never let Preller live down that Bogaerts contract unless his production drastically improves.


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