The A's Made a Trade So Disastrous, It Landed Them on a Player's No-Trade List

There is some steep competition for the worst A's trade this century, but this one takes the cake

Apr 6, 2009; Los Angeles, CA, USA; Oakland Athletics left fielder Matt Holliday (5) bats during the 2009 Opening Day game as Los Angeles Angels catcher Jeff Mathis (center) and home plate umpire Charlie Reliford (left) look on at Angel Stadium. Mandatory Credit: Kirby Lee/Image of Sport-Imagn Images | Kirby Lee-Imagn Images

The Athletics have made some excellent trades over the years, especially in the early 2000s, when they were able to scoop up a new lights out closer seemingly every season. They've also had some clunkers.

While most fans will point to the 2014 trade of Yoenis Céspedes to the Boston Red Sox in exchange for a half-season of Jon Lester and Jonny Gomes, there was at least some logic that went into that deal.

What are the three worst A’s trades since 2000? If you had to keep one of those three, which would it be?

— Jason Burke (@ByJasonB) October 29, 2025

Not to defend it by any means, but the thought was that the club didn't have enough pitching (hence the trade for Jeff Samardzija earlier in the month), and after being shut down by Justin Verlander in Game 5 of the ALDS in two straight seasons, they went out and got an ace.

Outside of Lester not being able to throw to first against a running team like the Kansas City Royals in the AL Wild Card game, it worked out great. You could also point to some other factors in that game, like leaving Lester in for as long as they did, the injury to the better throwing catcher Geovany Soto, or Gomes being in left field in extra innings as other reasons for the loss.

Instead, it was the A's trade with the Colorado Rockies that is the worst for our money. They acquired Matt Holliday, which was a big-time move for a big-time player, but they also gave up a young Carlos González, an effective Huston Street, and Greg Smith for what ended up being a half-season of Holliday.

When Holliday signed a deal years later with the New York Yankees, he had a one team no-trade clause, and that club was the A's.

Holliday went on to play fine for the Athletics in the first half of the 2009 campaign, batting .286 with a .378 OBP and 11 home runs in 93 games, but he seemed pretty stoked to get traded to the St. Louis Cardinals, where he hit .353 with a .419 on-base and 13 home runs in just 63 games played the rest of the way.

Why This Deal Was the Worst

July 20, 2009; Oakland, CA, USA; Oakland Athletics outfielder Matt Holliday (5) is congratulated after scoring against the Minnesota Twins in the first inning at Oakland-Alameda County Coliseum. Mandatory Credit: Cary Edmondson-Imagn Images | Cary Edmondson-Imagn Images

Not only did the A's give up some pretty good talent in order to land Holliday in Oakland for 93 games, but the team wasn't even necessarily just one piece away from contention, either.

After making it to the American League Championship Series in 2006, they finished with 76 wins in 2007, and 75 wins in 2008. That offseason they traded for Holliday, and with him on board for part of the season, they won 75 games again.

At least with the Céspedes trade, or even the Josh Donaldson trade, there was a clear direction for the franchise and supporting evidence. The argument can certainly be made that trading away the biggest bat in the lineup may not be the best move, and that deal led to the Donaldson one, but the front office believed that their window was closing, and they made a push. They tried.

With the Holliday move, it seemed more like they were throwing stuff at the wall to try and make it back to the postseason.

In an awful twist, the production they got from Holliday's 120 OPS+ that season was just a hair better than Car-Go's 118 for the Rox in 89 games. They could have kept him, developed him, and ended up with a homegrown star, instead of chasing a veteran that ended up putting them on the no-trade list after a few months in Green and Gold.

Moving Huston Street made a little bit of sense. After winning AL Rookie of the Year in 2005 with a 1.72 ERA, his ERA sat at 3.73 in 2008 and he had three more years of team control remaining. The other move the A's could have made here would have been holding onto Street and hoping for a rebound, then moving him by himself.

The Holliday trade ended up setting the franchise back for a couple of more seasons, when they made a miraculous run to the AL West title in 2012.

Which deal do you think is the worst? Let us know on Twitter/X!