Some MLB trades simply don’t pan out.
Others pan out for one team, but not the other.
Or, rarely, you’ll sometimes see a deal where both teams walk away completely satisfied.
Trades are risky business, and today, we’re going to break down a couple of the most lopsided ones.
The question we are looking to answer is: What are the two most regrettable trades in recent memory that involved trading away a future star?
2. Arizona Diamondbacks Trade Pitching Prospect Trevor Bauer And Two Other Players To Cleveland Indians For Shortstop Didi Gregorius
In 2012, the Arizona Diamondbacks made one of the worst decisions in franchise history.
Now, this gets a bit convoluted, but Gregorious lasted just one season in Cincinnati (and only appeared in eight MLB games) before he was traded again.
Let’s try to figure out exactly what Gregorious turned into for Arizona.
Leyba was largely a bust, but Ray was decent during his tenure with the team.
He pitched to a 4.11 ERA over six seasons with the team.
Then, Ray was eventually traded for relief arm Travis Bergen.
Bergem was with the Diamondbacks for just a couple of months before leaving in free agency.
So, in summary, the only player of substantial value that the Diamondbacks ever got multiple seasons out of was Ray.
That was essentially the team’s return for Bauer.
That’s an unforgivable mistake.
Bauer has gone on to become one of the most dominant pitchers in baseball.
He has won a Cy Young Award, an ERA title, and has received MVP votes in two seasons.
The Bauer strut is back 👀
— FOX Sports: MLB (@MLBONFOX) June 24, 2021
It’s safe to say that Diamondbacks fans will never let this one go.
1. Chicago White Sox Trade Prospects Fernando Tatis Jr. And Eric Johnson To San Diego Padres For Starting Pitcher James Shields
This trade went down in 2016, and it’s going to be remembered as one of the most lopsided deals in MLB history.
The Chicago White Sox ended up getting two-and-a-half seasons out of James Shields, and the results were miserable.
He pitched to a 6.77 ERA in 2016, a 5.23 ERA in 2017, and a 4.53 ERA in 2018.
He finished his time with Chicago with a 0.8 WAR.
The White Sox bought Shields’ stock when it was at an all-time high, and it crashed when he arrived with the team.
Shields was an attractive arm at the time of the deal for a couple of reasons.
One, he was extremely reliable.
From 2013 to 2015, he led the league in games started and pitched north of 200 innings in each campaign.
Two, his numbers were very good.
From 2011 to 2015, Shields posted a 3.30 ERA over 167 starts, a massive sample size.
There was no way of knowing that he was going to fall off a cliff like he did.
Now, let’s go over what the White Sox gave up.
Fernando Tatis Jr. was merely a prospect at the time of the deal, but he’s far from that now.
The 22-year-old is in his third MLB season, and he already has a Silver Slugger Award, a top-four MVP finish, and a top-three Rookie of the Year finish to his name.
Tatis currently leads the National League in slugging (.657), OPS (1.022), OPS+ (186), home runs (22), and stolen bases (15).
So far, he is a career .296 hitter with a .974 OPS.
Tatis is becoming one of the faces of baseball, and the White Sox have to sit back and watch it happen while he wears another team’s uniform.
You guys voted that Fernando Tatís Jr. is the Face of Baseball! pic.twitter.com/O9ZWkjhGIe
— Talkin’ Baseball (@TalkinBaseball_) March 20, 2021
The Eric Johnson piece of the deal hasn’t worked out, but it seems safe to assume that the San Diego Padres are just fine with the way things unfolded.