Revisiting the 2015-16 MLB Offseason

With a finished offseason that saw millions of dollars burned in free agency, it feels appropriate to talk about an offseason that can serve as a cautionary tale: the 2015-16 free agency class. This offseason was one of the first that I paid attention to. I was just starting to be a fan of the MLB. I had just learned the players on each team, and seeing them move to other teams made it even more tricky to learn them. Safe to say, I was completely blind to how utterly terrible this offseason was. Players exiting their prime or on the risk of decline were getting far too much money for the back half of their years. It's ironic since the Kansas City Royals just won the 2015 World Series with only the 17th-highest payroll. Of course, some good contracts, so let’s start with them first.

Zack Greinke: 6-year, $206 million ($34.33 million AAV)

There was a big risk that this contract could've been a disaster for the Diamondbacks. Zack Greinke had a masterful 3 years with the Dodgers, but the Dbacks signed him to a deal that would take him to his mid-to-late 30s. Other than a velocity drop and a down 1st year, it worked out pretty well. Greinke was as good as expected for the Diamondbacks except he dominated with control instead of velocity. He was incredible for the Dbacks in the 2017 playoffs. Sadly, the Snakes had a down year in 2018 and were looking to rebuild, so they shipped him off in 2019 to the Astros for several failed prospects. There, he would take a back seat to Justin Verlander and Gerrit Cole (before he got a big payday), but he was a key contributor to their first legitimate World Series title. He was even able to get one more contract with the Royals for a reunion in 2022.

J.A. Happ: 3-year, $36 million ($12 million AAV)

This deal had even more risk to fall apart than Zack Greinke’s. Happ had been below average at best for about six seasons with the Blue Jays, but after a meh season with the Seattle Mariners, he was shipped to Pittsburgh at the deadline. He caught fire, boasting a 7-2 record and a 1.85 ERA on the way to a playoff appearance for the Pirates. With that scorching end of the season, he was bound for a rich contract. It would be with his old squad the Blue Jays. Some were considering his contract a little of an overpayment. Little did they know that J.A. Happ would maintain his form from Pittsburgh and become a borderline ace pitcher for Toronto. He finished 6th in Cy-Young voting in 2016 and made an All-Star appearance in 2018. The renaissance of J.A. Happ deserves its own article.

Daniel Murphy: 3-year, $37.5 million ($12.5 million AAV)

            Murphy was a guy I thought would be super overpaid in free agency. He was a decent player on the wrong side of 30 who became the best postseason bat on a Mets team that just made it to the World Series. Surprisingly, the division rival Nationals were able to snag him on a rather reasonable contract. With the Nationals, his postseason dominance transferred to the regular season, as he made the All-Stars in the 1st two years of his deal and was solid, albeit not dominant, in the playoffs. Unfortunately, the Nationals never made it out of the 2nd round, and in September of a hectic 2018 season, they shipped him off to the Cubs as a rental. Unfortunately, his decline would be even sharper after Colorado signed him to about the same AAV in 2019. At least he was good with the Nats.

Dexter Fowler: 1-year, $13 million

            Dexter Fowler was on the market for a long time. With all the star outfielders on the market, he wasn’t getting the attention he deserved on the hot stove. On February 25th, he went back to the Cubs on a prove-it deal. He indeed proved his worth in 2016, achieving a 4.0 WAR season, an All-Star Appearance, and a ring. Not too shabby. It was enough for division rival St. Louis to grossly overpay for him in 2017 with a 5-year, $79.5 million deal. He would fall off a cliff in Year 2 of the deal and was shipped to the Angels in 2021. I guess he was always a Cub at heart.

Ian Desmond: 1-year, $8 million

            This was the same situation as Dexter Fowler. He was unsigned for a long time in this cycle, which was odd because it wasn’t a particularly deep infield class. To be fair, Desmond’s defense wasn’t amazing, but still serviceable. He latches on with the Rangers on a 1-year deal and a potential playoff push. The playoff push never happened, but Desmond didn’t disappoint, delivering an All-Star Appearance for the squad. Unfortunately, the Rangers botched his glove, as he was forced to move to CF and LF since Elvis Andrus occupied short. I guess the Rockies took inspiration from this and signed him to a lucrative contract to play 1B in the 2019 offseason. He fell off in Coors. At least this deal worked out.

Marco Estrada: 2-years, $26 million ($13 million AAV)

            Estrada had filled in nicely from a depth starter in Milwaukee to a similar role in Toronto. He even finished in the top 10 in Cy-Young voting in 2015. Toronto rewarded him with a 2-year extension. Of course, he was 32, so there was worry of his decline. In 2016, he was standard Estrada: an underrated pitcher who was even more underrated in the postseason. He made an all-star and got a playoff win. Unfortunately, the good luck would end there, as he fell off a cliff in 2017, with his ERA ballooning to 4.98. He would be out of the league in 2 years.

Asdrubal Cabrera: 3-year, $24 million ($8 million AAV)

            After Murphy left, the Mets didn’t take long to find their replacement at 2B. Of course, it was a downgrade, because what’s the Mets without signing hand-me-downs? Asdrubal Cabrera was far from his prime in Cleveland, but he was still a decent player with Tampa Bay. He would be the standard Cabrera we all know and love: solid bat, terrible defender, sometimes a headcase. Of course, it didn’t help that the Mets evolved into a clown show in 2017-2018. He was exiled to Philadelphia for a random prospect in the final year of his deal. He signed with the Rangers in 2019 before being DFA’d, picked up by Washington to replace Daniel Murphy, catching fire for a month, and winning a World Series with the Nats. Not bad for having to spend 3 years on the Mets.

Kenta Maeda: 7-year, $25 million ($3.125 million AAV)

            I mean, for how dirt cheap the contract was, Maeda would’ve outperformed it if he averaged a 5.00 ERA. He wasn’t what he was from Japan, but at least he was fine. That makes him one of the better contracts in this cycle.

Ben Zobrist: 4-year, $64 million ($16 million AAV)

            Alright, this one is bound to be a little controversial. Signing a 35-year-old to a $16 million per year deal, then watching him oscillate from solid to terrible every other year shouldn’t be worth it, right? Well, that’s where the postseason comes in. Ben Zobrist put his name on this list by winning the World Series MVP for the Cubs, including hitting the game-winning RBI in extras. He was critical in breaking the over 100-year Curse of the Goat for Chicago. He’d done the same thing for the Royals a year earlier, and he was decent anyway, so it's not like he was a total liability for them.

            That’s it. Those are the only contracts that either didn’t disappoint or didn't become disasters. Time to go down the rabbit hole of insanity.

Disclaimer: I’m not going after the players who signed these contracts. If anything, they should be praised for how they took care of themselves and their families from these contracts. It’s never a player’s fault for a team giving them a big contract. Players need to take care of themselves and their families, so taking advantage is their right.

Yasiel Sierra: 6-year, $30 million ($5 million AAV)

            We start with a pretty modest contract. Yasiel Sierra was a prospect who defected from Cuba to test free agency, and he was rewarded with a 6-year contract with the Los Angeles Dodgers to develop into a front-line ace. Safe to say, he was far from it in the MLB. In fact, he never even made the MLB. That’s right: the Dodgers paid $5 million per year for the equivalent of Taro Tsujimoto. For all the terrible contracts out there, at least they played in the MLB.

Brett Anderson: 1-year, $15.8 million

            Another contract given out by the Dodgers makes this list. Brett Anderson was coming off of an OK season in his first year as a frontline starter, but the Dodgers wanted to buy into the idea he could be a solid innings eater, so they signed him to a prove-it deal that could become a megadeal if he proved his worth. Safe to say, he didn’t prove his worth. The man went 1-2 with an 11.81 ERA before a bulging disk ended his season. He would stay in the league for a few seasons despite never having over a 3-WAR season. Regardless, I think the Dodgers could have used that cap space more wisely.

Gerardo Parra: 3-year, $27.5 million ($9.16 million AAV)

            The Rockies had seen a lot of Parra in Arizona: a scrappy center fielder with plus speed and an insane glove in the outfield. After arguably his best season with the bat last season with Milwaukee and Baltimore, Colorado took the bait, signing the 29-year-old to a 3-year deal. What happened since then? Well in 2016, he was one of the league’s worst hitters. 2017 and 2018 weren’t much better. Before you ask, his glove didn’t come with him from Arizona. This mistake was one of the many reasons why Colorado could never get over the hump in 2017 and 2018.

Byung-Ho Park: 4-year, $12 million ($3 million AAV)

            Similar to Yasiel Sierra with the Dodgers, Byung-Ho Park was brought in by the Minnesota Twins to make it to the majors and be a power-hitting 1st baseman, kinda like a poor man’s Pete Alonso. At least Park played a season for the Twins, but it wasn’t good. He was so bad in Minnesota that he was demoted to Rochester in 2017 and went back to Korea in 2018. A man who consistently got over 1.000 OPS in the KBO couldn’t even scratch .700 in the MLB. This signing and the Yasiel Hernandez signing probably made people wary of signing Shohei Ohtani.

Yovani Gallardo: 2-year, $22 million ($11 million AAV)

            Much like Marco Estrada, who I mentioned earlier, Gallardo spent most of his career being a solid mid-rotation starter for the Brewers before pitching his best season ever with the Rangers on a prove-it deal. He should’ve gotten at least one Cy-Young vote in my opinion. I guess the Baltimore Orioles agreed and signed him to improve their beleaguered starting pitching staff in 2016. Remember, this was at the time they had a reputation for being a SP graveyard. Unfortunately, the death of Yovani Gallardo’s career started here in Camden Yards, as he fell off to the point where he wasn’t even a member of the Orioles rotation at the end of the year. Baltimore exiled him to the Mariners at the end of the year, where he continued to look rough on the mound. He would only pitch 2 more seasons. What a weird falloff from such a promising pitcher.

Scott Kazmir: 3-year, $48 million ($16 million AAV)

            Man, the Dodgers swung and missed on 3 different rotational arms. Kazmir was the most heinous of the 3 examples of gross budget management from the Dodgers. They gave him this contract going into his mid-30s! He pitched 1 full, below-average season before lingering hip issues forced him to be sidelined for 2 YEARS! The hip discomfort forced him to change his delivery completely. He would be shipped to Atlanta in a salary dump for the brief resurgence of Matt Kemp. He was able to make a brief comeback in the MLB with the Giants in 2021, though. Of course, injuries hampered this deal more than anything ever could’ve. Regardless, the Dodgers could’ve used a mulligan here though.

Ian Kennedy: 5-year, $70 million ($14 million AAV)

            This is a textbook small-market team move. The Royals were looking to re-sign trade deadline acquisition Johnny Cueto, but he was priced out of their plans, so they had to scramble for any option. Ian Kennedy was a decent mid-back rotation starter who seemed to have his best days behind him in Arizona. The Royals paid him well into his mid-30s. Kennedy had his best season in a while in 2016, where he threw 195.2 innings of 3.73 ERA ball, but then came the steep decline and the realization they threw a ton of money at a mid-pitcher in his early 30s! Kennedy would fall off a cliff so hard that he wasn’t even on the team’s starting rotation after year 3 of the deal. If anything, he mirrored the Royals franchise after the World Series run: a .500 record and decency followed by a complete and rapid decline.

Alex Gordon: 4-year, $72 million ($18 million AAV)

            The Royals also had to deal with resigning their key batters. Here was the list of batters who would be free agents in the next two years: Salvador Perez, Eric Hosmer, Lorenzo Cain, Mike Moustakas, and Alex Gordon. As a small-market team, they couldn't resign them all, so they had to choose carefully. Gordon was the first person they chose to resign, but while he made 3 All-Stars in the last 3 years, he was signed into his mid-30s and had a massive risk of declining. Sadly, the fan favorite did indeed decline. He won 3 Gold Gloves through the contract, but his offense was so poor, it didn’t even matter. To add salt to the wound, they saw Eric Hosmer and Lorenzo Cain leave the next offseason, and Mike Moustakas was traded to Milwaukee after no one would pick him up (for whatever reason). It was a scenario where they were damned if they did or damned if they didn't, but I think Kansas City would’ve chosen differently here.

Wei-Yin Chen: 5-year, $80 million ($16 million AAV)

            The Marlins were looking for some rotational depth in new manager Don Mattingly's first season. They saw Dan Haren retire recently, so why not take a swing at Wei-Yin Chen, someone who pitched a 3.44 ERA in Baltimore? To leave a quality pitcher from the graveyard of Camden Yards was almost a miracle, so he should be decent right? Unfortunately, his career with the Marlins was, to put it nicely, unimpressive. His 1st year was regression, with nagging injuries and a 4.96 ERA to boot. 2016 was a tragedy for both him and the Marlins, as their ace pitcher Jose Fernandez tragically died at the end of the season. No one on the Marlins staff stepped up to the ace role in 2017, especially not Chen, who suffered a torn UCL. In 2018, it was just more ineffectiveness before the Marlins put the contract out of its misery with a DFA in 2019. In 2020, he was the MLB’s highest-paid player despite never making it to the majors. To think that if this deal hadn’t blown up spectacularly, the Marlins could’ve potentially resigned Yelich or J.T. Realmuto.

Mike Leake: 5-year, $80 million ($16 million AAV)

            Who thought it was a good idea to give Mike Leake an average of $16 million annually? It’s not like he regressed in any way after the deal, this was just a textbook overpayment. The Cardinals seemed to agree, as not even a year after signing the contract with him, they traded him to the Mariners in exchange for just about nothing. They still had to retain about $4-6 million of his salary. This isn’t as bad as Wei-Yin Chen’s deal, but it’s still lavish.

Jeff Samardzija: 5-year, $90 million ($18 million AAV)

            Weirdly enough, the Shark was one of my favorite pitchers when I was just starting to be a fan of the MLB. I have to be honest, though: I saw this being an albatross of a contract from the beginning. San Francisco wanted to make a bevy of upgrades to their rotation to escape dreaded mediocrity. As a result, they signed Samardzija and another pitcher I will mention here soon. The Shark had just come off of a depressed season with the White Sox, so the fact he still got this much is insane. Again, he didn’t regress or fall off that much: he just never played to the level of the contract. His career 4.24 ERA with the Giants isn’t bad, but would you say it’s worth around $18 million a year? I don’t think so.

Yoenis Cespedes: 3-year, $75 million ($25 million AAV)

            Cespedes will go down as one of the most underrated players of the 2010s. After the Mets acquired him in the 2015 trade deadline, he played like an MVP candidate. With that kind of talent at not even 30, you have to lock him up long-term. The Mets did, with a 3-year, $75 million deal, and he rewarded them early on with an All-Star appearance and votes for MVP in 2016. So why is he on this list? Simple: he had an opt-out after his first year on the deal. He chose to execute it, forcing the Mets to sign him to a new 4-year, $110 million deal in 2017. Ever since then, his career was completely marred by injuries, not even playing a full season’s worth of games through 4 years. He sustained a broken ankle fighting a bore on his ranch, an injury that would end his career. Typical Mets luck.

Jordan Zimmerman: 5-year, $110 million ($22 million AAV)

            The Tigers were in the latter stages of their window at this point, but owner Mike Ilitch knew his time was running short and wanted to keep the window open for World Series contention. Dave Dombrowski was just fired for trading away pieces at the deadline, so the objective was to compete and sign anybody necessary. Jordan Zimmerman was coming off of a down year with Washington, but who cares when you’re the owner and you want your team to compete? He was signed to a massive contract that would take him to his mid-30s. Zimmerman would never have an ERA under 4.50 in his entire career with Detroit, rapidly declining to the point where he had a 1-13 record and a 6.91 ERA in his final season. The tragedy wouldn’t just end there: Mike Ilitch died in 2017, never seeing the Tigers make a World Series. After his death, the Tigers have not ended a season with a winning record since. Ilitch wanted to keep the team in contention for the World Series before he passed away, but with contracts like these, it looks like it damaged the team more than they could repair.

Justin Upton: 6-year, $132.75 million ($22.125 million AAV)

            Upton was another player that Mike Ilitch signed to an insane deal due to his desire to keep the window alive in Detroit. Fortunately for Detroit, they didn’t see the contract fall apart. After two and a half seasons, the Tigers were nowhere near World Series contention, so they shipped him off to the Angels in a post-deadline trade in exchange for a failed prospect. After an ok year with the Angels in 2018, Upton’s body broke down on him, never starting for more than 90 games in a season. He wasn’t producing in the games he played in either. Another one bites the dust.

Johnny Cueto: 6-year, $130 million ($21.67 million AAV)

            I thought this contract would be a good deal for the Giants. Cueto was a bonafide superstar to be the 2nd ace alongside Madison Bumgarner. In his first season, he rewarded them with an All-Star selection, placing 6th in the Cy-Young competition and garnering MVP votes in the process. Ever since, though, there has been complete and utter regression. He was so injury-prone to the point where he never started more than 16 games again on the deal. It’s not like he was any good when he started. Outside of 2018, he didn’t have an ERA under 4 in any of the remaining seasons on his deal. After his contract, he would briefly return to form with the White Sox in 2022 on a minor league invite. Too bad the White Sox weren’t keen on winning, but it just proved that if he could still be his elite self, he would’ve been in San Fran. Too bad.

David Price: 7-year, $217 million ($31 million AAV)

            David Price was one of the best pitchers of the early 2010s. During a stretch from 2010-2015, Price had a 94-49 record with a 2.97 ERA. A guy with 6 straight All-Stars and That was the pitcher that Boston was hoping they’d get when they signed him to the biggest contract in this free-agent cycle. He was never actively bad, but he never reached that Cy-Young form again. The highest WAR he had in a season was 3.7, which is above average. I don’t think the Red Sox paid $31 million per year for slightly above average. At least he won a ring with the Sox. Even then, I feel like Boston media still has a grudge against him for the contract, his public spat with Dennis Eckersley, and the fact that they had to trade franchise player Mookie Betts to get his contract off the books.

Jason Heyward: 8-year, $184 million ($23 million AAV)

            I thought this contract would be a home run for the Cubs. A 26-year-old star entering the market is a rare sight in the MLB, and I thought his glove and bat would continue to develop. This was supposed to be the piece to push the Cubs over the top and win a title. They did win the World Series in Heyward’s 1st year, but for Heyward, nothing went right. He still had 2 Gold Gloves with the Cubs, but his hitting regressed to the point where he was constantly put in the 9-hole in most lineups. It was one of the strangest regressions in MLB history, and the Cubs had to eat through all but 1 year of the contract. In 2023, the Cubbies had enough and mercifully bought him out of the contract. He would join the Dodgers on a league minimum deal and become a quality Major Leaguer again, so there’s a happy ending for him at least. Just not for the Cubs, as contracts like his prevented them from supplanting their roster further and becoming a dynasty.

Chris Davis: 7-year, $161 million ($23 million AAV)

            DING DING DING DING DING!!! Chris Davis is the biggest reason why I wrote this whole article! Out of all the regrettable contracts ever signed in the MLB, this has to be the nadir. I guess Peter Angelos wanted to break the narrative that he was holding his Orioles back with his cheapness, so he chose to sign Chris Davis, a streaky, power-hitting 1B who was now locked up until his mid-30s. We all laughed at the impending decline that would come in the latter part of the deal, but no one could’ve predicted how horrible it turned out for the O’s. Davis was declining by year 2 of the deal, and by years 3 and 4, he turned into a borderline black hole. I’m not exaggerating he was statistically the WORST POSITION PLAYER two years in a row!!! He had a streak of 51 games without a hit that spanned for 2 seasons! The Orioles were paying him $23 million per year to do nothing but strikeout and play terrible defense. In 2020, they had to buy out the remaining 3 years of his contract to where he’s still earning $5.7 million until the end of this year and will be earning $2.8 million until 2037. This deal wasn’t just terrible, it’s the reincarnation of Bobby Bonilla Day. It nearly single-handedly set the Orioles franchise back for 5 years.

Most people who read articles from this website know about the risks of free agency signing. Any big transaction is a gamble, but to have so many of the big-ticket items disappoint or completely disintegrate to ash is appalling. More than $3.7 billion were spent in this free agent period all for most teams to have regret 2 or 3 years into the deal. Look at how many of these players were either bought out early or traded to other teams in salary dumps. What did MLB teams learn from this? Something, probably. No offseason has seen that much money be spent on free agents since. The only one to even get within $100 million is 2022-23, and that free agency class featured guys like Trae Turner, Aaron Judge, Carlos Correa, Max Scherzer, and Justin Verlander. It goes to show how truly odd the 2015-16 free agency class was.