Past failures guide Alex Anthopoulos' decision-making process as Braves GM

Previous experience with bad deal has led to Alex Anthopoulos becoming one of baseball's best executives.
Toronto Blue Jays Introduce Jose Reyes
Toronto Blue Jays Introduce Jose Reyes / Tom Szczerbowski/GettyImages

Alex Anthopoulos is one of Major League Baseball's best General Managers and is known for always making the right move at the right time. How could he be so good at addressing needs without handcuffing the team?

Well, the answer is simple, he's learned from past mistakes. Anthopoulos has been working in MLB front offices for almost 20 years at this point. He's had ample time to learn what teams should and should not do.

Whether that be a major free agent signing or swinging a blockbuster trade to win the offseason. Every fan base wants their team to make big moves but sometimes those moves can hurt the team unintentionally.

Alex began his career as a baseball executive with the Montreal Expos back in 2002 as a scouting coordinator. He then joined with the Blue Jays in 2003 in the same position and the Montreal native spent 12 years in Toronto. Eventually, he moved to the assistant general manager position in 2005 until being named general manager in 2009. That's where Alex truly shined and displayed his ability to make stealthy moves that improve the team.

AA remained with the Jays until accepting a VP of baseball operations role with the Dodgers in 2016 before landing with the Braves as executive vice president and general manager in November of 2017 after John Coppollela was fired for committing rule violations in the international player market.

Atlanta Braves fans have gotten used to their stealthy GM making moves that no one expects and it paying dividends for the team. He has made a few head-scratching moves but that's bound to happen. He rarely makes a move that doesn't make sense for the Braves and that's because he's learned from past mistakes and adapted.

Anthopoulos faced a real challenge when he took over the Blue Jays as GM in 2009 as he inherited one of the worst farm systems in baseball at the time. He eventually transformed it into one of the best and that also allowed him to have prospect capital for some massive trades.

He still has that ability to this day as fans saw during the 2021 season where AA had to rebuild his entire outfield which led the team to a World Series title.

Moves that refined Alex Anthopoulos' decision making

One of his first moves as GM was a controversial one as he traded Hall of Famer Roy Halladay to the Phillies. The Jays acquired Michael Taylor, Kyle Drabek, and Travis d'Arnaud in return. Taylor was immediately sent to the Oakland A's for Brett Wallace. Drabek was eventually released from the Jays in 2015 and Travis d'Arnaud, who is dear to Braves fans, was included in a trade for R.A. Dickey in 2012 that sent him to the Mets.

Trading a franchise pitcher is never an easy move but it was made to build up a depleted farm system. Still, in hindsight, the deal wasn't that great as every player acquired was eventually flipped elsewhere. Also included in that deal for Dickey was Noah Syndergaard who became a great piece for the Mets for a few seasons.

However, trades were one of the strong suits of AA and that remains true today. Examples of good trades include offloading Vernon Wells' massive contract to the Angels, getting Mike Napoli in return, and acquiring Josh Donaldson for Brett Lawrie, Kendall Graveman, Sean Nolin, and Franklin Barreto.

The David Price trade was a mixed bag as he really helped the Blue Jays out big time and pitched extremely well. However, Toronto had to trade away a few good prospects including Matthew Boyd at the time. Price was a rental and ended up signing with the Red Sox after that season.

Other examples of trades gone awry include trading Justin Nicolino, Henderson Alvarez, Anthony DeSclafani, Yunel Escobar, Adeiny Hechavarria, Jake Marisnick, and Jeff Mathis to the Miami Marlins for John Buck, Emilio Bonifacio, Mark Buehrle, Josh Johnson, and Jose Reyes.

That move was meant to make the Blue Jays contend in 2013 but this move backfired as only Buehrle had a positive season. Braves fans will notice that AA added Adeiny Hechavarria to Atlanta's 2019 and 2020 rosters later on. That's something that fans will notice, Alex has reunited with former players over the years including Josh Donaldson, Jose Bautista, and Travis d'Arnaud.

The biggest flop that comes to mind as a mistake that taught AA a lesson, is acquiring Troy Tulowitzki and LaTroy Hawkins in exchange for Jeff Hoffman, Jesus Tinoco, Miguel Castro, and Jose Reyes.

Now, the names sent in return weren't amazing but Jeff Hoffman was considered a good prospect at the time. Hoffman has just now become a known name in baseball as he had a great season in relief for the Phillies in 2023. Tulowitzki seemed like a massive win but his career had quite the decline after that deal.

He performed decently in 2016 but an ankle injury in 2017 pretty much ended his career. He was released by the Blue Jays and then picked up by the Yankees but only had a few at-bats before hitting the IL and eventually retiring.

Those trades were all necessary and helped the team for the most part but I think the ending to those moves has influenced how AA decides trades now in Atlanta. He's not made a trade for a big-name player unless he believes it helps the team. For example, adding Matt Olson and Sean Murphy required a good amount of prospects but the trade-off is both acquired players signed contract extensions immediately.

Another area AA has shown more caution is signing free agents. Atlanta fans have shown a bit of frustration at times over the years due to AA not signing big-name free agents in the offseason but that's because that route has come back to bite him in previous years.

For example, Russell Martin was inked on a five-year, $82 million deal in 2014. His 2015 season was All-Star worthy and he earned a spot on the AL team and 2016 was decent as well. However, 2017 and 2018 were not great and Martin's career with the Blue Jays ended.

That deal shows why AA is a bit cautious with free agency and the biggest deal he's handed out to a free agent is the Marcell Ozuna deal and... the Cole Hamels deal. Sorry for bringing up past trauma.

Ozuna's had a roller coaster ride with the Braves but luckily, it looks like that deal may end on a positive note...hopefully.

Most of Anthopoulos' big moves have been contract extensions for players acquired like Olson and Murphy. He also locked up Ronald Acuna Jr, Ozzie Albies, Austin Riley, Spencer Strider, and Michael Harris II because he believes in their talent and knows they are more valuable than hoping a free-agent signing works out.

So, AA still moves in the shadows when making deals and is very creative in how he acquires talent to fill team needs. The 2023 offseason has been a great example of a typical offseason with Alex at the helm. He's acquired players in deals to flip them soon after.

Anthopoulos has become arguably the best GM in all of Major League Baseball and there's a reason for that. He's taken his collective experience and refined how he makes moves and improves the organization. The creativity never ended but there is a bit more thought behind trades or free agent signings now.

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