In August 2014, the San Diego Padres signed A.J. Preller to their front office and just 13 months later, the Seattle Mariners signed Jerry Dipoto into theirs. Preller and Dipoto are two of the most well-known names in the industry because of their big trades and tumultuous tenures. 

Inspired by baseball YouTuber Jolly Olive, who has chronicled the “insane” trade history of the Seattle Mariners and San Diego Padres, it is time to look at the impact these two executives have had on their respective franchises. 

While free agency is a huge factor in both men’s positions in the front office, they are better known for their habits on the trade market. 

First off is Preller, who joined the Padres in the hope that he could be the key to getting them into contention with the division giants of the Dodgers and Giants. 

From the jump, Preller was on the phone swinging massive trades to overhaul the roster and put the team into contention. The hype was unreal for his team as he got several All-Star caliber players for some prospects. Sadly for the team and Preller, the tumult started as the team showed quickly that they were not a contender. 

A couple of the trades that are notable was the padres trading with the division rival of the Los Angeles Dodgers to acquire All-Star outfielder Matt Kemp. Kemp was a very good player, but the price paid was high. Most notably, they sent off catcher Yasmani Grandal, who would be one of the best catchers in the entire league for years to come. 

Also traded off in other trades were starting pitcher Max Fried and shortstop Trea Turner, two of the best players in their current positions today. 

After just one season, Preller began a fire sale where he sent off a couple of the pieces he had traded for in the previous year. Although they would not immediately prove to be the right moves, in the long term he won several of these deals big. 

In a trade with the White Sox, Preller found a lowly international prospect by the name of Fernando Tatis Jr. and only had to give up James Shields. He also found a cowboy-hat-wearing starter from Miami in Chris Paddack for Fernando Rodney. 

These two specific trades signaled a change in the tenure of Preller, as they would eventually be the key to the return of playoff baseball in San Diego. 

Preller took a couple of years off from making massive trades, although notably, he sent off the prospect and now current Mariners pitcher Luis Castillo, someone who certainly would benefit the current team. 

His break ended at the end of the 2019 season. In a big trade, he got Trent Grisham and Zach Davies from the Brewers, who have both been successful for the team in their time. He also signed legendary third baseman Manny Machado to a long-term contract to hold down the hot corner in San Diego. 

That trade holds no candle to what he would do over the next two offseasons. Since then, Preller has acquired Jake Cronenworth, Mike Clevinger, Yu Darvish, Blake Snell, Joe Musgrove, Josh Bell and Sean Manaea. 

Even so, the biggest pieces he has acquired came at the 2022 trade deadline. Preller, going all in for not only this year, but the next three to five seasons acquired two notable players that were huge targets for all teams. 

First was reliever Josh Hader, who came into the season not really on the radar to be on the move, but due to some mid-season struggles, the Brewers were looking to move on from the lefty. 

While in any other season this would easily be the biggest move, the Padres and Preller were not done.

In a trade with the Washington Nationals, they got the generational talent of Juan Soto for a haul of prospects including MacKenzie Gore, Robert Hassell and CJ Abrams, who were supposed to be the future of the Padres. But when you can get a talent such as Soto, you jump on that and try to win a ring. 

Even with all of these moves, he is rivaled by Dipoto and the Mariners. In just seven years, he has made over 120 trades. 

Just like his counterpart in Preller, the early trades were less than ideal for the Mariners. While not as detrimental as losing players such as Turner and Fried, Seattle lost several pieces that could have aided in ending the playoff drought a couple of years before they actually did.

Players being sent away from the team between 2015-17 included Logan Morrison, Brad Miller, Mark Trumbo, future All-Star Chris Taylor, Andrew Kittredge and Ryan Yarbrough. These names have all provided notable major league production, but the positive later in his tenure far outweighs the losses from his early trades. 

Even in a transaction that the Mariners got big cornerstones of Mitch Haniger and Jean Segura, they sent away Ketel Marte, who could easily fill in the hole at second base that the team is currently experiencing. 

It took a while for Dipoto to land another big win and he even lost a future big prospect in Pablo López in a trade with the Marlins, but the start of the 2018 season turned the tide for the Mariners. 

Through several trades and in trading away Robinson Canó and Edwin Díaz, the Mariners acquired J.P. Crawford, Jarred Kelenic, Tom Murphy, Shed Long Jr. and Nestor Cortés Jr. 

The caveat on Cortes Jr is that he only made a few starts for the team before heading back to New York, but it is quite crazy to think that he was a part of the team for any period of time. 

While during the 2021 season Dipoto fell out of favor with the clubhouse due to a trade that sent Kendall Graveman to the division rival Houston Astros while both teams were in the thick of a postseason hunt, worst of all it was in the middle of a series between the two teams. 

However, during that next offseason, he reignited hope for the franchise.

In just one offseason and into the regular season, Dipoto acquired Eugenio Suárez, Jesse Winker, Luis Castillo and in a trade with the Preller-led Padres acquired former All-Star Adam Frazier. 

Both Preller and Dipoto have been highly regarded in many of their recent trades, but nothing matters until your team actually wins. 

In 2022, both teams looked to do that as the Padres made it to the NLCS and the Mariners finally made it back to the postseason. 

Fans of both franchises hope that 2023 can be the year that they finally get their World Series ring and if all goes well, we could even be looking at a matchup of the Mariners and the Padres in the World Series where the best executive will win.