Major League Baseball is a money driven league. Cash is king, and if you don’t have much, one wrong move can set your organization back for years. We’ve seen it happen countless times – a “small” market team tries to run with the big spenders and ends up crippling their financial capabilities going forward when an expensive Free Agent doesn’t pan out. Teams in the playoff hunt ship off their prized prospects for rentals and end up missing the playoffs anyway. Star pitchers rake in cash only to tear their arms two years into a six year deal. It’s the nature of the beast.
With baseball players having guaranteed contracts, every signing feels like a gamble and trades rarely tend to work out for both parties. For every Marlins franchise that has buyer’s remorse on a Giancarlo Stanton, there’s a Yankees franchise waiting to take on the bulk of the contract without blinking an eye. Even in today’s analytical landscape trades and signings seem to go south more so than not. Players demand no trade clauses, opt outs and vesting options that teams try their best to block from activating.
You either shell out the cash, or take an Astros-like approach and finish last for years to build up your farm. It’s almost like there is no in between anymore, but you gotta be in it to win it. Every offseason there are at least a couple of signings that instantly look like head scratchers, and in the era of Free Agency and $30 million dollar a year players, anyone can be moved at any time. Here are 15 recent moves teams are already regretting.
15 Alex Gordon
Alex Gordon has been a stalwart in the KC lineup for close to a decade, so it was no shock the Royals locked their guy up with a 4 year, $72 million contract after winning the World Series. Gordon is a defensive wizard who brings value to a team even in times where his bat is lacking… but not that much value. After a dismal 2016 season, Gordon actually rated as the WORST player in baseball statistically for a stretch in 2017. It’s hard to believe the Royals are kicking themselves too much after being just two years removed from a ring, but they are now stuck with two more seasons of Gordon making over $20 million. This is especially troubling when you realize they will probably have to let franchise cornerstones like Eric Hosmer, Lorenzo Cain and Mike Moustakas walk this offseason.
14 Jason Heyward
This one seemed questionable from the get-go. It’s rare for a player to reach free agency at a young age, but when Jason Heyward hit the market at 26, teams were lining up. Despite not really delivering on his offensive promise yet, his potential and his elite defensive skills made him seem like a cornerstone player. Heyward’s Free Agency period came at the “right time.” The Cubs ultimately came out the victor in the Heyward sweepstakes, paying the outfielder $184 million over 8 years. It’s hard to feel bad for the Cubs, who went on to win the World Series that year, but Heyward was basically relegated to the bench during their run. He improved in his second season, but not enough to warrant the money he’s “earning.” While his incredible glove cannot be denied, it’s not even a given he starts for the Cubs in 2018. That would be one expensive platoon player.
13 Zack Greinke
If you just go on numbers, Zack Greinke was one of the best pitchers in the National League last season. Unfortunately there’s more to modern baseball than just statistics. When a team signs a player to a long term contract they are pretty much already resigned to the fact they’ll probably regret the final years of the deal. Greinke, who will turn 34 in 2018 and is under contract until 2021, still has about $140 million owed to him. Reports are the D-backs are already trying to cash in on Greinke’s 2017 season, but would probably still have to eat some money on his deal if they expect someone to trade for the All Star. We’ve reached a point in baseball where you can’t even trade one of your best players without picking up some of the money on the contract.
12 David Price
If an ace hits the market, you could all but guarantee the Red Sox will be in on him. That was the case when David Price hit Free Agency before the 2016 season. Boston and the former Rays ace came to terms on a 7 year, $217 million deal. Price proceeded to put up his worst ERA since his first full season in the majors. Players usually get a one season grace period after a big contract, so Sox fans weren’t too worried, especially when you consider Price still struck out over 225 batters that year. In 2017, Price seemed to be back on track, before injury derailed his entire season. With more than $150 million still left on his deal, and his reputation of being a pretty unreliable postseason pitcher, the Sox must be regretting this one. There were even whispers he might not be a shoe-in for the rotation in 2019, but that seems highly unlikely.
11 Mark Melancon
Spending big money on “reliable” relief pitching has become a necessary evil in today’s game, but sometimes it can really come back to bite. Relievers are a fickle bunch. While there are some truly elite backend pitchers in baseball, there are significantly more who can go from lights out one season to mediocre at best the next. Mark Melancon was one of the upper echelon closers in the NL when he signed a 4 year, $62 million dollar contract with the Giants last offseason. The Giants proceeded to finish with the worst record in the league. With most of the money owed to him backloaded, and the history of relievers with injured pitching arms disappearing off the map, I’d be pretty nervous right now if I were a Giants fan.
10 Johnny Cueto
I’d be nervous on this contract as well. You could probably count how many truly great long-term pitching contracts there have been in the last decade on one hand. We’re just two years into Johnny Cueto’s 6 year, $130 million contract with the Giants, and they probably wish they can hit the reset button. Cueto was coming off a solid 2015 season which saw the longtime Reds ace get dealt to the eventual World Champion Royals when he signed in San Francisco. His first season in orange and black was a good one. He finished sixth in Cy Young voting and made the All Star team. His second season was not even close. In 2017 Cueto missed some time with injury while also putting up a 4.5 ERA and 1.5 WHIP. With four years remaining on the deal, and his mid-30s approaching, the Giants might just end up having another albatross on their books.
9 Felix Hernandez
If I would have told you a few years ago that Felix Hernandez would become virtually unable to be traded, you would have called me nuts. It’s hard to kill a team for rewarding their franchise player with a huge contract. Seattle had a Cy Young winning ace in their grasps, and pressure from the fanbase to keep him around for life, so they did the now regrettable thing, and extended King Felix to a 5 year, $135 million contract before the 2013 season. While he remained elite the first few seasons, it’s been a steady decline ever since. Felix has hovered around league average the past couple years while making $25+ million a season. The Mariners are still on the hook for over $50 million more, and it seems like their stuck with their former ace for the life of the contract.
8 Jordan Zimmermann
There is zero doubt the Tigers are kicking themselves over this one. Jordan Zimmermann was one season removed from finishing 5th in the NL Cy Young voting when he hit Free Agency. While his 2015 season was a step back, he was still about to hit the open market under 30 years old. For good measure, he went out and pitched a No Hitter in his final start as a National. That following offseason the Tigers signed him to a 5 year $110 million contract. In his two seasons in Detroit, Zimmermann has put up an incredibly bad 5.60 ERA, and has been worth .05 WAR. The Tigers paid $18 million each season for a replacement level player. The Tigers must be praying for a miracle, because Zimmermann is due to make $24, $25, and $25 million in his next three years respectively. Ouch.
7 Ian Desmond
When Ian Desmond was playing short for the Nationals in 2014 he reportedly turned down a 7 year, $107 million contract. The Nationals must be thanking their lucky stars. Desmond proceeded to have a disappointing walk year and was forced to sign a one year “show me” contract with the Rangers. Not only had his offensive game hit a lull, he was moved off short and into the outfield, which would seem to be a hindrance when looking for a big money deal. The Rockies didn’t seem to mind, as they signed Desmond the following offseason for 5 years and $70 million to play… first base? One could argue versatility adds value to a player, but this seemed strange from day one. Desmond got hurt before the season, and only ended up playing 95 games in his first year in Colorado.
6 Zach Davies
The Brewers have made some shrewd under the radar trades over the past few years, and this one has a chance to be the best of the bunch. At the 2015 trade deadline, the perpetually starting pitching starved Orioles traded their then #3 prospect Zach Davies to the Brewers for Gerardo Parra. Parra was supposed to be a key piece to propel the Orioles to the playoffs. You have to give to get during a playoff push, but this trade ultimately ended up being a bust. The Orioles missed the playoffs, and Parra signed with the Rockies in the offseason. Davies on the other hand has already shown signs of brilliance in his two seasons with the Brewers, and at just 24 years old analytics say he’s only trending up. You gotta think Baltimore wishes he was slotting into their rotation right now.
5 Khris Davis
After showering them with praise, it’s only fair I mention a trade the Brewers are probably already regretting. Khris Davis showed plenty of signs while playing three years in Milwaukee, but that didn’t stop the Brewers from dealing him in the 2016 offseason to Oakland for a couple prospects. Prior to the trade, Davis hit 27 homers for the Brewcrew. After the trade, he has hit 42 and 43 homers in his two seasons with the A’s. While the A’s have been basement dwellers, Davis has blossomed into one of the AL’s most feared power hitters. On the other side, the Brewers are close to playoff contention, and you can’t tell me they couldn’t use a 40 homer bat making reasonable money in their lineup. You win some, you lose some. At least they aren’t saddled with the next contract on the list.
4 Chris Davis
After a few years of promise in Texas, Chris Davis became an absolute monster with the Orioles. In 2013 he finished third in MVP voting and hit an astronomical 53 homers. He had an injury plagued season the next year, but came back strong in 2015 with 47 homers. He also led the league in strikeouts. In the new age of baseball you can live with strikeouts when the other offensive numbers are in the stratosphere. That must have been what Scott Boras sold the Birds to get them to pony up a 7 year, $161 million contract to Davis at age 30. In the two seasons since, his strikeout pace remained the same, but the rest of his offensive numbers dropped off drastically. With five years and $115 million left on his deal, the Orioles are definitely regretting this one already.
3 Shelby Miller
This one resulted in almost instantaneous regret. Shelby Miller, a former top Cardinal prospect was actually traded to Atlanta for another player on this list, Jason Heyward. In 2015, Miller put together an All-Star pitching season for the Braves, and appeared to be delivering on his former stud prospect promise. That offseason, out of nowhere, the Braves dealt him to the Diamondbacks for a package which included the first overall pick in the draft, Dansby Swanson as well as outfielder Ender Inciarte. Miller’s first season in Arizona was an absolute nightmare. His second season wasn’t much better, appearing in just four games before going down for the year with injury. The trade was so bad, it cost D-Backs’ GM Dave Stewart his job. Still, at age 23, the Braves are more than happy to wait him out. Although if he doesn’t break out soon, they may be regretting a trade they made a few weeks prior.
2 Andrelton Simmons
In the 2015 offseason, the Braves traded one of their core players in Andrelton Simmons to the Los Angeles Angels. Simmons had already cemented himself as the best defensive shortstop in baseball, but had never really shown much promise at the plate, so the Braves figured they’d cash in while his value was still high. Since the trade, Simmons’s bat has begun to come alive. In his first season in LA, Simmons put up a career high batting average, and had his best power season. In 2017, he improved his OPS by nearly one hundred points, and hit 38 doubles. When you factor that in with his defense, Simmons sported a 7 WAR, which was top five in the American League. If the trend continues, he may just become a MVP candidate in the coming years. The Braves are ready to roll with Swanson, but you have to think they’re kicking themselves a little over this one.
1 Jake Arrieta
Ok, this one is a bit of a cheat. I wanted to predict who I thought would ultimately sign the most regrettable contract this offseason and I landed on Arrieta. It’s tough to sit here and fault a guy for not replicating what he did during his incredible 2015 season, but Jake Arrieta is trending down and I suspect he’ll still land a monster contract. While he’s still putting up stats any team would welcome with open arms, he could barely be a league average pitcher in a few years if the trend continues. The game is so desperate for top flight pitching these days that it’s not hard to see an AL team splurging on a guy like Arrieta to come over and be their “Ace.” Arrieta is already being predicted to get upwards of $140 million, which is a massive gamble for a pitcher over the age of 30. If you choose to invest in players like this, you’re just asking for trouble at this point.