T10YL - 2014 MLB Trade Deadline, Part 2
Four more trades, all of which concern the Red Sox in some form.
This is part two of our 2014 MLB Trade Deadline recap, which covers the remainder of the trades that took place in advance of deadline day. Part 1 is linked below:
July 26, 2014 (5 days pre-deadline)
The Names: San Francisco Giants receive: Jake Peavy. Boston Red Sox receive: Edwin Escobar, Heath Hembree.
The Team Context: The two teams involved in this trade had won three of the last four World Series. The Red Sox had done so more recently (2013), but the Giants had done so more frequently (2010 and 2012). In 2014, it was already clear that the Red Sox were not going to be back-to-back champions as they sat in last place on July 26. This question was less clear for the Giants; they had led the NL West for most of the season, but that lead was slipping away in July. The Dodgers had just come to town on July 25 and started their three-game series with a win to cut the division lead to one game. On July 26, the Dodgers won again to cut the division lead to zero games.
The Player Context: Most recently, Jake Peavy had been an incredibly successful deadline acquisition. The Red Sox had traded for Peavy on July 30, 2013, slotting him into their rotation on their way to a championship. Peavy had joined the Red Sox after four seasons with the Chicago White Sox, the best of which was an All-Star (and Gold Glove) season in 2012. But everybody knew Jake Peavy because of the excellent start to his career in San Diego, which started in 2002 but peaked with a unanimous Cy Young award in 2007. He was the best pitcher in baseball that year and in the conversation for a couple surrounding seasons.
That conversation seemed quite distant in 2014. Peavy went 1-9 in the 20 starts he made with the Red Sox in 2014 while facing regular rumors about the organization’s desire to fill his rotation spot with one of their upcoming pitching prospects. He was rumored to be headed to the Cardinals or the Braves in early July, but both teams ended up denying their interest. Any team that would finally pull the trigger on acquiring Peavy accepted that they were signing up for a reliable backend starter rather than the ace connotations that lingered with the name “Jake Peavy” at the start of the 2010s.
The Giants gave up a pair of pitching prospects who seemed much more exciting before the 2014 season began. In December 2013, John Sickels evaluated Edwin Escobar as the 2nd-best prospect in the San Francisco system and Heath Hembree as the 8th-best. Escobar was the 56th-best prospect in baseball according to Baseball America, thanks to two strong seasons where he made the minor leagues look easy through AA as a 21-year-old. Escobar was going to be a starter and would likely be in MLB before much longer. Heath Hembree had never been anything but a reliever, but had already made it to the majors in September of 2013 and made 9 shutout appearances. You didn’t need to do any projection whatsoever to envision Hembree as a useful member of a bullpen.
Things had diminished for both men in 2014. Hembree had returned to AAA and only pitched decently. He was 25 and running out of time for the Giants to feel comfortable with him as a major league reliever. Escobar was taking on AAA for the first time and getting bombed at the level, with better hitters showing a much greater ability to avoid striking out against him.
The Trade: The most common pattern of MLB trade is that a bad team will send veteran players on their roster to a good team in exchange for some minor league prospects from the good team’s farm system. Somewhere around 99.7% of fans of the bad team have limited familiarity with the minor leaguers playing in the good team’s system, so they quickly look up prospect rankings for that good team. Occasionally, they’ll read the scouting report or look at the statistics that underlie these prospect rankings, but more typically they will just look at the ranked numbers and express joy [or dismay] that they were [only] able to get the good team’s [X]th-best prospect.
The reaction to this trade features fans of all stripes expressing the sentiment that this was an overpay from San Francisco. After all, Peavy had been quite poor in 2014, and Escobar and Hembree were the #2 and #8 Giants prospects. A small minority of fans, all of whom rooted for the Giants, were able to point out that more recent information had updated the proper frame with which to view Escobar and Hembree, but they were drowned out by the broader outdated consensus.
Eno Sarris at Fangraphs called this a win-win trade and expected Peavy to see much better results. An extreme flyball pitcher like Peavy could see success in the pitching-favored home stadiums of San Diego or San Francisco, but would reasonably struggle in the smaller dimensions of Fenway Park. “The Giants are getting what should be – in their ballpark – an average to slightly above average major league starter,” Sarris said.
The Results: Jake Peavy made his first start for the Giants the day after this trade to close out his new team’s series against the Dodgers. He allowed three runs in six innings and took the loss, completing a Los Angeles sweep that put the Giants one game back in the NL West. They would stay in second place for the rest of the regular season, never catching up to the Dodgers again. I don’t have to write about whether the Giants went on to win the 2014 World Series as a Wild Card team if I don’t want to. I retain complete editorial control over Trades Ten Years Later. Don’t like it? I might edit out the part from earlier about the Giants winning the World Series in 2010 and 2012, don’t tempt me. The San Francisco Giants finished the 2014 season in second place in the NL West.
Peavy got off to a slow start in San Francisco. He had worn number 44 on his uniform throughout his career, but switched to 43 on arrival since his prior number was retired for Willie McCovey. Peavy lost his first three games as a Giant, allowing ten earned runs, and decided to switch back to the number 22 he had worn in high school. In hindsight, it seems obvious that the uniform number 22 was a better spiritual successor to 44 than 43 could possibly have been, a theory that is borne out by the results. Peavy only allowed nine earned runs over his final nine starts as he cut his season-long ERA from 4.73 to 3.73. He signed a two-year contract to stick around in San Francisco that paid him $24 million in total.
Boston was able to get both of their additions from this trade onto the major league roster by the end of the 2014 season, during which they each posted identical 4.50 ERAs. Escobar only made it to the Red Sox for those two 2014 appearances; he spent 2015 in AAA and was waived during the 2016 season. By contrast, Hembree stuck around in Boston for quite a while as a serviceable reliever until he was traded at the 2020 trade deadline. The 1.8 WAR that Hembree compiled across seven seasons in Boston was just under the 1.9 WAR that Jake Peavy compiled in his twelve starts as a Giant in 2014, so I suppose San Francisco wins this one, even if they could only manage to finish second in the NL West.
The Aftermath: Edwin Escobar threw 23.2 more MLB innings for Arizona in 2016, then went to Japan for the 2017 season. His first year with the Hokkaido Nippon-Ham Fighters was moderately effective, but he took a substantial step forward following a midseason trade to the Yokohama DeNA BayStars. Escobar was an entrenched member of the BayStars until this season, when he signed a minor league contract and threw 46.1 innings for the AAA Iowa Cubs. The organization released him on July 16, and he signed with the Sultanes de Monterrey on July 22. In a ludicrously small two inning sample, Escobar’s Mexican League ERA is 13.50 (EDITOR’S NOTE: Escobar pitched last night and now has a Mexican League ERA of 9.00 in a ludicrously small three inning sample).
After a period of stability on the Red Sox, Heath Hembree became an MLB journeyman starting with his trade to Philadelphia in 2020. 2021 brought Hembree to each of the Mets and the Reds, while 2022 saw him spend time with both the Pirates and the Dodgers. He was a Tampa Bay Ray for the first month of 2023, but then transcended to MiLB journeyman as he joined the AAA Toledo Mud Hens. Hembree made nine appearances in the Mariners’ minor league system this year, all between June 13 and July 13, before he was released on July 20.
Peavy’s ending had less baseball, but more twists and turns. Just before the start of the 2016 season, he learned that his financial advisor Ash Narayan had allegedly stolen upwards of $33 million from him and other athletes to invest in a money-losing company called The Ticket Reserve. Peavy’s losses were particularly heavy and he was a key witness in the SEC’s case, required to fly to the Northern District of Texas (Dallas) throughout the year for court proceedings. Just after the end of that same season, Peavy’s wife filed for divorce. With so much going on away from baseball, Peavy ended up sitting out the 2017 season to spend time with his four sons, saying “there’s no way in a million years that I could leave my boys at this time” in February but “I can tell you with certainty, without a shadow of a doubt, I will play baseball again” in June. He eventually targeted a comeback for the 2018 season and scheduled a showcase for May 1, with the late date conforming to his son Jacob’s school schedule. But on May 20, that showcase still hadn’t happened.
The next concrete update came in May 2019, when Peavy abandoned any pretense of a comeback and officially retired from baseball. It’s not like he was short on things to do – besides the four children, Peavy had founded a recording studio in Mobile called Dauphin Street Sound and operated a number of other businesses in town. He’s started working as an on-air personality at MLB Network in the past couple of years, and spent his 2024 trade deadline hosting a television special about other people’s trades rather than getting traded himself.
July 28, 2014 (3 days pre-deadline)
The Names: Toronto Blue Jays receive: Danny Valencia. Kansas City Royals receive: Erik Kratz, Liam Hendriks.
The Player Context: I like this trade because its main contribution to the literature is to elucidate just how stupid all of this is. A live action game of Mad Libs that millions of people have chosen to emotionally and financially invest in.
Let’s start with the fact that all three of these players started the 2014 season at AAA despite making their MLB debuts in either 2010 (Valencia and Kratz) or 2011 (Hendriks). Let’s also note that the longest-tenured player involved in this trade was Erik Kratz, who had been traded to Toronto on December 3. Valencia had arrived in Kansas City a couple of weeks later in a December 18 trade for David Lough. Hendriks had started his career in Minnesota and was designated for assignment on December 5, but it took until February 21 for him to make it to the Blue Jays (he had layovers with the Cubs and Orioles during the offseason, each of whom claimed and then subsequently waived him).
The Danny Valencia for David Lough swap from December 18 is a milestone transaction in the history of Trades Ten Years Later, as it marks the first time I looked at a trade on my schedule and decided that not a single person in the world actually wanted to read about it. We hadn’t launched by December 3, but the swap of Erik Kratz and Rob Rasmussen for Brad Lincoln would have been a close call.
The point is that these were three fringe MLB players; the sort of guys who could be the 22nd best player on the right roster. And those were generally great outcomes for each of them. Erik Kratz was a 29th round draft pick from Eastern Mennonite University in 2002 and spent the first seven offseasons of his professional baseball career working construction jobs to make money. Liam Hendriks was signed from his hometown of Perth, Australia, where he played on a high school team that had been “set up purely for [him] and another guy.” Danny Valencia was drafted in the 19th round of the 2006 Draft from the University of Miami, which he only got into via transfer from UNC-Greensboro after the Hurricanes didn’t recruit him in high school.
But not all fringes are equally fringey. If you squinted, Erik Kratz was a viable backup catcher. Liam Hendriks could be a backend starter or long reliever. Danny Valencia could be a starting third baseman, at least against left-handed pitchers, which is a bit better than the other outcomes described. It also required less squinting, with Valencia currently rocking an OPS+ that was just 2% worse than a league average hitter. Kratz’s OPS+ was 40% worse than a league average hitter and Hendriks’ ERA+ was 36% worse than a league average pitcher. Both were spending plenty of time in AAA Buffalo.
The Trade: The best part about the trade deadline is getting new players on your team. The worst part is giving up players, particularly when they’re players that you follow and think are good. That makes these so-called “trash-for-trash” trades particularly engaging for fanbases; they don’t know much about the player they just got, but they know the player they just traded away isn’t very good. The effect is particularly pronounced in a two-for-one swap like this, since Jays fans could appreciate that their team was actually receiving the better-regarded player. Since they were receiving the better fringe, it was only fair that they gave up twice as many fringes.
The Results: Again, I feel compelled to lead with the conclusion that this particular trade was “stupid” before confounding that analysis with details. The swap had a marginal effect on both teams involved.
Here are the details that could mislead you: Kratz and Hendriks both performed substantially better in Kansas City than they had in Toronto during the 2014 season. By contrast, Danny Valencia’s performance took a pretty big step back. The Blue Jays went on to miss the playoffs entirely, while the Royals made an improbable run to the World Series. Were Kratz or Hendriks involved in that 2014 Royals postseason run? The hypothetical argument is going to fall apart if we explore that question, so let’s ignore it.
The teams began undoing this transaction immediately after the 2014 season, when Liam Hendriks was traded back to Toronto on October 30 (literally one day after the Royals lost World Series Game 7). Erik Kratz failed to stick on the Royals’ roster in 2015 and was released in June after reaching base zero times in five plate appearances. Interestingly, Danny Valencia seemed to make progress at hitting right-handed pitchers in 2015, starting the season hitting 24% better than league average by OPS+. The Blue Jays did not believe in this improvement and waived him after the trade deadline, allowing the Oakland Athletics to snag him for free.
The Aftermath: The second-most notable thing Danny Valencia did in an A’s uniform was to continue his progress as an improved hitter. He maintained “24% above league average by OPS+” for the duration of his season-and-a-half in Oakland, the best mark he posted with any team. Extremely respectable on-field performance. The first-most notable thing Danny Valencia did in an A’s uniform was punch his teammate Billy Butler in the head during a clubhouse altercation after Butler made comments about Valencia wearing off-brand cleats in front of an equipment rep. Butler and Valencia each left the team shortly thereafter, with Valencia traded to Seattle for the 2017 season and moving on to Baltimore for 2018. His affiliated baseball career ended in August after the Orioles released him, but continued for the next five years when he became an Israeli citizen (after being raised Jewish in South Florida) and started playing for the Team Israel baseball team. This included both the 2020 Summer Olympics and the 2023 World Baseball Classic, though he only had one hit across four group stage games in the latter tournament. Now he’s a real estate agent with a website that maybe hasn’t been updated in two years. A property at 901 SE 7th Ave in Delray Beach listed as “WATERFRONT BRAND NEW CONTSTRUCTION (sic)” on Valencia’s website was sold in May 2023 for $6.6 million and is now being listed by a different real estate agent, who set the price at $8.38 million in January and cut it to $7.75 million in May.
Erik Kratz managed to play for nine different MLB teams across his 332 career games, including two separate stints with each of the Phillies and Pirates. His transaction log is a nightmarish ball of yarn that cannot be untangled. Between 2002 and 2020, Erik Kratz spent substantially all of his time employed by a major league baseball organization. But because his service time was so sporadic and involved so many detours through minor league systems, Kratz had reported career earnings of just under $4 million. The actual number is probably somewhat higher, since this figure excludes minor league salaries and airline miles.
That brings us to Liam Hendriks, who had already yo-yo’d back to Toronto by the end of October. In 2015, the Blue Jays had the great idea of putting Hendriks in the bullpen, where he immediately excelled. Toronto took their found Australian dollar and exchanged it for a more stable currency by trading Hendriks to Oakland for Jesse Chavez, who had recently converted the other direction and become a solid starter after several early-career years in relief. For a while, it seemed like a smart sell-high; Hendriks pitched more like a “solid bullpen piece” than a worldbeater and he was even sent to AAA in 2018. He was part of a fun gimmick when he was used as an “opener” in the 2018 AL Wild Card game, though it got less fun after he gave up a two-run home run to Aaron Judge and the A’s lost.
During Hendriks’ quick 2018 jaunt to AAA, he picked up a long toss program that led to significant increases in his velocity. He turned 30 ahead of the 2019 season and surged to become one of the American League’s best relievers, making his first All-Star team and then sticking around in the upper echelon of closers for each of the next four seasons (two as an Oakland Athletic and two with the Chicago White Sox). The only thing that could slow Hendriks’ run of dominance was a January 2023 diagnosis of non-Hodgkin’s lymphoma, which caused him to miss the start of the season as he underwent chemotherapy. Fortunately, Hendriks was declared cancer-free on April 20 and could begin preparing for his return to MLB. Unfortunately, it was shortlived, because there’s always a lurking boogeyman that can slow any pitcher’s run of dominance. Hendriks made his first appearance of 2023 on May 29 and his last appearance of 2023 on June 9, after which he was placed on the injured list with elbow inflammation that eventually required Tommy John surgery.
Hendriks became a free agent after the 2023 season and, despite the ongoing injury recovery, signed with the Red Sox on a two-year, $10 million contract in February. At the time of signing, Hendriks set a goal of returning to pitch in Boston by the trade deadline. He seems to have missed that goal, but he did throw a 35-pitch bullpen that day and hopes to be cleared to return to facing hitters soon.
July 30, 2014 (Deadline Eve)
The Names: Chicago Cubs receive: Felix Doubront. Boston Red Sox receive: Player to be Named Later (Marco Hernandez).
The Team Context: The key connection here is that Theo Epstein had left his post as General Manager and Head Cursebreaker with the Red Sox to take a promotion with the Cubs after the 2011 season. He still had some former colleagues at Red Sox HQ from three years prior.
The Player Context: Felix Doubront was a young pitcher from Venezuela who had helped to fill out the back half of the Boston rotation in recent seasons. Doubront was first called up in 2010 and got another cup of coffee in 2011, but didn’t settle into a role until 2012 and 2013, when he made 56 starts for the Red Sox. He pivoted to the bullpen when the playoffs came around and picked up the win in Game 4 of the 2013 World Series.
Doubront resumed his work out of the rotation in 2014 but had a 5.12 ERA when he made his penultimate start for the team on May 20. Doubront allowed five runs in four innings and struggled to throw his fastball above the mid-80s, revealing after the game that he “couldn’t feel [his] shoulder” after slamming it into a car door. The injury and its cause were unknown to the Red Sox until after the start and they were understandably irritated to place him on the disabled list after he had already pitched terribly during a game.
When Doubront returned from injury on June 20, he was announced as a starter and Red Sox fans weren’t necessarily thrilled. After that, Doubront was moved to the bullpen and was well beyond “not thrilled,” still viewing himself as a starting pitcher. By July 27, he was frustrated enough to openly vent his frustration to reporters. I don’t want to quote the entirety of his multi-paragraph tirade, but the heart of it can be distilled to the contiguous quote “I don’t know what they’re doing. I know they’re not doing the right thing for me.” There were other gems too, like “they don’t see the numbers, they don’t care what I’ve done in the past. It’s hard to be happy like that with these guys.” This screed did not sit well with Boston fans, who were happy with the concept of getting rid of Doubront for “a bucket of balls and a pack of gum.” Doubront upped the ante on July 28, when he faced ten batters and got two of them out (one of whom hit a sacrifice fly and got an RBI). Contemporary reports said that “the disgruntled southpaw looked disinterested while surrendering six earned runs over two thirds of an inning,” and Doubront and manager John Farrell had a private meeting after the game.
The Trade: If you’re going to have a massive public feud with your team as an ineffective MLB player, July 27 is a pretty considerate time to do so. It’s a little too late for the team to fully shop you around, but presumably they’ve had some idea of your simmering discontent before you blathered to reporters about it. Besides, you spent July 28 getting blown up to increase your season ERA to 6.07 — it’s not like you had trade value anyways.
Fortunately for the Red Sox, they were friendly with a former colleague who faced no pressure to field a good baseball team in 2014. For Theo Epstein, who ran the team when Doubront signed back in 2005, it was easy to see the pitcher as a promising youngster rather than a poor-performing malcontent. Nobody had serious expectations for Doubront in Chicago, but because they were one year removed from acquiring Jake Arrieta at the deadline, everyone felt obligated to mention that this situation had some similarities. But, as effectively synthesized by Dave Cameron, “not every Jake Arrieta works out, though, and Doubront probably won’t.”
The Results: Mixed bag. The starts that Doubront made in his time in Chicago were pretty good, but there were only four of them. He pitched to a 3.98 ERA across 20.1 innings, managing to keep a reasonable ERA despite striking out just 8 batters and walking 7. The Cubs released Doubront ahead of the 2015 season. Because he was generally below replacement level throughout his career, the 0.4 WAR he produced in Chicago is his best total with any team (all the other totals are negative).
Nobody paid much attention to what the Cubs were going to get back, including the teams involved, who simply agreed to decide on a player after December’s Rule 5 Draft. That player ended up being Marco Hernandez, who got off to a hot start in the minor leagues in 2015. Hernandez was added to the 40-man roster after the season and made his MLB debut in 2016, making this trade at least somewhat of a win for Boston. He almost found a niche as a backup utility infielder, but a devastating shoulder injury in May of 2017 required two surgeries that kept him from making it back to the major leagues until June of 2019. Hernandez stuck on the Boston roster that season, but was released after the year. His final MLB plate appearance was a pinch-hit opportunity against the Orioles, when he came up with runners on first and third but lined into a double play.
On reflection, it’s less of a “mixed bag” and more of a “win-win” with wins so small that they can’t be viewed without a special microscope. Both teams can look at this transaction and conclude that they got some value while giving away nothing material.
The Aftermath: Doubront’s post-trade career had enough international movement to make a Trades Ten Years Later NBA post blush. The first stop was Canada (technically international), where Doubront signed with the Blue Jays to begin the 2015 season. He was traded to the A’s for cash at the deadline, pitching worse there than the already mediocre performance he had turned in for Toronto. Doubront required Tommy John surgery in April of 2016 but remained in the A’s organization, returning to pitch for the Nashville Sounds in 2017. But he was used as a reliever for Nashville, which we know he doesn’t like.
Thus ended Felix Doubront’s American baseball career. He signed with the Lotte Giants in 2018, returned to the rotation, and pitched to a 4.92 ERA in 25 starts. That wasn’t good enough to stick in a rotation in Korea either, so Doubront turned to the Mexican League. His first stop was Pericos de Puebla in 2019, leaving midseason to join Saraperos de Saltillo. Doubront began playing in the Venezuelan Winter League in 2019-2020 and has continued to do so each winter since. But during the spring season in 2021, he took his talents to Taiwan and made 14 starts for the Uni-President 7-Eleven Lions. Doubront pitched to a 3.42 ERA in the CPBL but wasn’t re-signed, probably because Uni-President 7-Eleven Lion management was distracted by the 1.83 ERA and 17-4 record put up by a 6’8” Canadian guy named Brock Dykxhoorn. Doubront has been pitching in Mexico since then and has basically become a journeyman, evidenced by his February 8 trade from Leones de Yucatan to Dorados de Chihuahua followed by his July 22 trade from Dorados de Chihuahua back to Leones de Yucatan. Dykxhoorn, meanwhile, has been a stalwart of the Uni-President 7-Eleven Lion rotation.
The Names: St. Louis Cardinals receive: Justin Masterson. Cleveland receives: James Ramsey.
The Team Context: Both teams were having pretty mediocre starts. On July 30th, the Cardinals had the 7th-best record in the NL and Cleveland had the 9th-best record in the AL. That difference seems small, but approximates a pretty thick margin between teams that want to buy at the deadline and teams that want to sell. It also looks more meaningful when you use the actual records (St. Louis was 56-50; Cleveland was 53-54).
The Player Context: Five people born in Jamaica have gone on to play baseball in a major league. The first was Oscar Levis, who pitched in the Negro Leagues in the 1920s. The next three (Chili Davis, Devon White, and Rolando Roomes) were each born in Kingston between 1960 and 1962, then immigrated to the United States with their families in childhood (White and Roomes to New York; Davis to Los Angeles).
The fifth was Justin Masterson, who was born in Kingston in 1985. Justin’s father Mark was a pastor who had graduated from Fort Wayne Bible College in 1976 and Trinity International University (which is in Illinois) in 1980. During his time at Fort Wayne Bible College, he spent a year at Jamaica Theological Seminary, making such a strong connection that he returned in the 1980s to serve as Dean of Students and also have a son named Justin.
By 1990, Mark was the Lead Pastor at Creekside Community Church in Beavercreek, Ohio, which is charmingly described as “the second-largest suburb of Dayton.” Justin was a star at Beavercreek High School, “where he not only played baseball and basketball but was the homecoming and prom king, president of the student council, head of the Fellowship of Christian Athletes and in the National Honor Society.” Masterson started his collegiate career at Bethel College, a 1,200-student Christian school located three miles from Notre Dame that had produced zero MLB players at the time he enrolled. Actually, he was originally set to play at Notre Dame, but his scholarship offer fell through when he got food poisoning the night before a meeting with the coaching staff while visiting cousins who attended Bethel. When his cousins called Notre Dame the next morning to let the baseball coaches know that Masterson couldn’t make the meeting, the coaches assumed it was something more like “drink poisoning” than “food poisoning” and stopped their recruitment. I guess they didn’t buy the intensely Christian upbringing? (If you’re skeptical too, consider that this source is from two weeks ago and Justin Masterson really has no incentive to lie about being hungover in 2003 anymore).
After two dominant years at Bethel where he compiled 20 wins, 185 strikeouts, and hit 10 home runs, Masterson transferred to San Diego State, where he was drafted in the 2nd round by the Red Sox in 2006. He was seen as one of the top pitching prospects in baseball by 2008 and made his debut that year, pitching mostly out of the bullpen while sprinkling in a few starts. In 2009, Masterson was the centerpiece of a deadline trade that sent Victor Martinez from Cleveland to Boston. He was used as a reliever the day after his arrival, but then slid into the rotation and closed out his season by pitching a 12-strikeout complete game (he lost, but still).
Masterson spent the next few seasons as a cog in Cleveland’s rotation and a sort of sabermetric darling. Masterson got a lot of groundballs by feeding batters a high diet of fastballs and flashed tantalizing talent even as the total package seemed to fall a bit short of what it seemed like he could be. Masterson seemed to put it together in 2013 as he made his first All-Star team, but he missed three weeks in September with an oblique injury and could only return to the postseason roster as a reliever.
Masterson was entering his final year of team control in 2014 and rumors emerged that Cleveland might be willing to listen to trade offers, though these were shot down by manager Terry Francona a day later. The two sides expressed mutual interest in a multi-year extension, but a resolution seemed unlikely based on the large gap between Masterson’s and Cleveland’s arbitration filing figures. Masterson thought that a fair salary for 2014 would be $11.8 million, while Cleveland thought $8.05 million was more suitable, creating a $3.75 million gap that was larger than any other arbitration filer that year. They ended up settling roughly on the midpoint between those two numbers on a one-year deal, but Masterson told Cleveland reporters that his expectation was that “somehow, some way, I’ll end up still being here for a few more years.” He subsequently took matters into his own hands and offered to re-sign with Cleveland for “$40 to $60 million over three to four years,” a sizable discount compared to what similarly-qualified Homer Bailey had just signed for. “How can [Cleveland] say no?” asked Ken Rosenthal.
Two weeks later, Cleveland had yet to respond, which is one way of saying no. Two days after that, they countered with a substantially lower salary on a two-year deal that included a club option, which is another way to say no. Extension talks subsequently broke down, though all parties expressed interest in revisiting the concept down the road. “Although the doors are technically closed, they all have doorknobs so you can open them again,” Masterson said.
When his fastball velocity fell from an average of 93.1 mph to 90.5 mph as he dealt with a lingering knee injury to start the 2014 season, the sound of bolts turning echoed throughout Northeast Ohio. Masterson got crushed by the Yankees on July 7, allowing five runs in just two innings before he was pulled from the game. He was placed on the disabled list and never pitched again for Cleveland.
James Ramsey was St. Louis’ first round draft pick in 2012 out of Florida State. He was hitting well in the minor leagues, but was maybe ascending slower than you’d expect for someone who had spent four years in college. Ramsey had spent most of 2013 at AA and was back at the level as a 24-year-old in 2014. We’ll leave it at that given the eight paragraphs spent on Justin Masterson’s life story.
The Trade: Inquiries about Masterson’s availability began to make news on July 24. On July 28, Jeff Passan reported that Cleveland was “very willing” to trade Masterson away. By July 30, he was gone.
This was perhaps the peak of an era where you could assume that any pitcher the Cardinals acquired was going to start performing well. This could either be utilized as a low-effort meme or as the conclusion to an in-depth analysis about their top-tier defense. Either way, the thought process was clear. St. Louis gave up a pretty good prospect in exchange for a pitcher whose lurking talent they would surely maximize.
The Results: Justin Masterson made six starts for the St. Louis Cardinals. In four of those starts, he was charged with five earned runs, and in a fifth, he was charged with four earned runs. To his credit, there was also one gem where he surrendered three hits and no walks over seven shutout innings in Miami. I hope Cardinal Nation remembers that one start fondly. He moved to the bullpen in September and made three more appearances before leaving as a free agent.
James Ramsey never made it to MLB, so this is one of those conundrums where we have to decide whether it’s better to receive Nothing or receive Something that is technically an Active Liability. The actuarial answer is that spending [minor league salary approximating $0] on James Ramsey’s lack of contribution is preferable to spending something like $3 million to get one good start and five bad starts from Justin Masterson. But that feels like a pretty lame way to think about sports, particularly when we’re looking back at things a decade later. The Cardinals ended up with Justin Masterson, the former All-Star pitcher whose career merited eight paragraphs of discussion. Cleveland ended up with James Ramsey, who peaked in college. The former seems more fun.
The Aftermath: Masterson signed a one-year contract back in Boston for the 2015 season that guaranteed him $9.5 million and offered up to $2.5 million more in incentives, with every five inning threshold between 185 and 205 innings earning Masterson an additional $500,000. But whatever was wrong with him in 2014 continued to be wrong; Masterson was roughed up in the rotation and placed in the bullpen after returning from an injury in July. Like Felix Doubront, Masterson preferred to pitch out of the rotation; unlike Felix Doubront, Masterson said “I don’t know if it’s in my nature to do that, to say ‘Beat it guys, trade me or put me in [the rotation].” Also unlike Felix Doubront, nobody was even willing to put Masterson on their MLB roster. The Red Sox released him on August 19 after he threw just 59.1 innings (falling about 125 short of starting to earn incentives). Masterson pitched in the minors for the Pirates in 2016 and for the Dodgers in 2017, then officially announced his retirement after sitting out the 2018 season.
That means James Ramsey actually played organized baseball longer than Justin Masterson did, even if none of it is really worth caring about from our perspective. Ramsey was assigned to AAA on arrival in Cleveland, then stagnated there for the remainder of his career. 2014 and 2015 were spent as a Columbus Clipper, 2016 was spent as an Oklahoma City Dodger and Tacoma Rainier (where he returned for one game in 2017), and 2018 was spent as a Rochester Red Wing (Twins AAA) until May, when he was demoted to become a AA Chattanooga Lookout until June 24, when he was released.
This allowed Ramsey to finally get started on what seems like it will be the more impactful portion of his baseball career. Ramsey returned to his alma mater of Florida State in August and began working as an assistant coach on the baseball team. Before the 2019 season began, he had been hired away to become the hitting coach at Georgia Tech, a team that immediately blossomed to become the best offense in the ACC. Ramsey was subsequently promoted to associate head coach prior to the 2022 season, a title that unofficially designated him as the program’s head coach in waiting. Current head coach Danny Hall, who has held the position since 1994, told the Atlanta Journal-Constitution that “we gave him the title of associate head coach for a reason” and that “he’s going to get my endorsement for whatever he wants to do.” A 34-year-old “washed up minor leaguer” feels pretty old, but a 34-year-old “head coach in waiting” is basically a prodigy.
