Top 5 most gut-wrenching A's trades of the last decade
It will take at least a couple years to truly evaluate Monday’s trade of Sonny Gray, as is the case anytime the A’s deal for minor league prospects. But the immediate reaction from fans is clear: Another big-name player sent packing out of Oakland. Along that theme, here’s a run-down of the top five gut-wrenching A’s trades for fans to cope with over the past decade, from the least difficult to the most...
OF Carlos Gonzalez, RHP Huston Street and LHP Greg Smith to the Colorado Rockies for OF Matt Holliday (Nov. 12, 2008): This one sticks out for the premiere talent the A’s shipped off in Gonzalez, who went on to win three Gold Gloves and post five seasons of 25-plus homers for the Rockies. Holliday spent three underwhelming months as Oakland’s left fielder, never finding his comfort as an Athletic, then was dealt to St. Louis for a three-player package that was just as underwhelming. Connect the trading dots and the end result the A’s had to show for the original deal was outfielder Michael Taylor, who never panned out.
Sonny Gray and $1.5 million in international bonus slot money to the New York Yankees for IF/OF Jorge Mateo, OF Dustin Fowler and RHP James Kaprielian (July 31, 2017). No recency bias here: It was a tough pill for fans to swallow just because of the final-hour nature of it. The trade that put Gray in pinstripes didn’t get announced until an hour or so before the deadline. That gave fans just a glimmer of hope that maybe Gray would stick, but it was clear that the A’s best starter of the past four years was heading elsewhere, if not now then this winter. If the three prospects received end up blossoming, it’s a good deal for the A’s because they’ve got the starting pitching depth throughout the organization to absorb this blow moving forward.
SS Addison Russell, OF Billy McKinney and RHP Dan Straily to the Chicago Cubs for RHP Jeff Samardzija and RHP Jason Hammel (July 5, 2014). The A’s flipped the script with a “win-now” maneuver. They scored two veteran starters, and Samardzija in particular bolstered the rotation. But even when this move was made, there was a sense of how much the A’s gave up in Russell, at the time their most highly regarded prospect in many years. He quickly became a key player for Chicago and won a World Series ring in 2016. A’s fans had to cover their eyes.
Yoenis Cespedes and a Competitive Balance pick to the Boston Red Sox for LHP Jon Lester and OF Jonny Gomes (July 31, 2014). A deadline deal that A’s fans still shake their heads over. But acquiring Lester was an aggressive move aimed at trying to put them over the top as a World Series contender, and people forget how wobbly the rotation was leading up to this deal. It quickly became clear, however, how big of a void Cespedes left. The offense stumbled badly and the A’s barely squeaked into the Wild Card game, losing a heartbreaker to Kansas City. For some, this trade might rank No. 1 on this list. But it was a bold move to fortify a rotation that badly needed it. It simply did not work out.
Josh Donaldson to the Toronto Blue Jays for 3B Brett Lawrie, INF Franklin Barreto, RHP Kendall Graveman and LHP Sean Nolin (Nov. 28, 2014). To this day it has to remain the toughest for fans to digest. Donaldson was still quite affordable, entering his first year of arbitration at the time of the trade, then proceeded to win the AL MVP award with Toronto in 2015. The A’s only have two players left from that trade, though one (Graveman) has become a front-of-the-rotation presence when healthy and another (Barreto) is the team’s top prospect. You can sense the collective groan each time Donaldson comes to bat against the A’s as a Blue Jay.