top of page

Winning the Trade (Deadline) Game

Photo Credit: Jon Gudorf Photography, CC BY-SA 2.0 <>, via Wikimedia Commons

Another trade deadline come and gone. As has become all too common for baseball’s oldest franchise, the Redlegs are sellers. In less than a week, the Reds successfully unloaded two homegrown pitchers and two outfielders for a boatload of prospects. It’s a good thing the Reds went for quantity, because they seem to lack an eye for quality when it comes to these deadline deals.

Since Bob Castellini took over as majority owner of the Cincinnati Reds in 2006, the Reds have had 11 losing seasons, and, unless a miracle happens over the next two months, are staring the twelfth right in the face. Out of Castellini's five winning seasons, the Reds made it to the playoffs four times, never advancing once, winning just two of eleven postseason games. In the 2010 National League Division Series versus the Philadelphia Phillies, the Reds were no-hit in Game One by Roy Halladay. In 2012, the Reds blew a 2 - 0 lead in the NLDS to the San Francisco Giants, becoming just the second NL team to do so, and the first in MLB history to lose all three games at home. In 2020, the Reds were swept by the Braves in the NL Wild Card Series without scoring a single run.

Why am I forcing you to relive these postseason disasters? To drive home the fact that since the Castellini family took over in ‘06, the Reds have been bad. Bad in the playoffs, bad in the regular season, bad in free agency, bad in trades, bad in the draft, bad at developing players, bad at scouting players and bad at negotiating contracts. Basically, just bad.

With the trade deadline now past, this is a good time to take a look at the deadline deals of the past and see how (in)effective the Reds have been in making these trades since 2006. In this article, I’ve compiled many notable trades involving big league players that happened before the trade deadline. As such, trades that occurred in the offseason, or trades that occurred in the post-trade-deadline-waiver-period are not included. I also wanted to strictly look at the trades that have been made under Bob Castellini’s watch, so no trades that were made before 2006 are included.

In order to grade these trades, I devised a system: zero to five Castellinis, with zero being utmost perfection, and five being downright failure, you know…because having five Castellinis around is like getting thrown out at first from right field, four is like making the last out of an inning at third-base, three is like a fielder’s choice, two is like a line drive to center field, one is like a towering, second-deck home run, and zero is like Tom Browning throwing a perfect game.

Now, without further ado, please enjoy the Reds’ Trade Deadline Deals of the Castellini-Era!

Bill Bray

Photo Credit: BubbaFan at the English language Wikipedia, CC BY-SA 3.0 <>, via Wikimedia Commons

SS Felipe Lopez, RF Austin Kearns & RP Ryan Wagner to the Washington Nationals for RP Bill Bray, SS Royce Clayton, INF Brendan Harris, RP Gary Majewski & SP Daryl Thompson - July 13, 2006

Three young, former top prospects for the Reds leave town in the middle of one of the team’s best starts in ages. Why? Pitching! Unfortunately, none of the players the Reds traded for panned out. Majewski was bad from the get-go, Clayton was washed up, Harris wasn’t ready to be a contributor for the Reds, and Thompson would only make four MLB-appearances in his entire career. As for Bray…well, Bray was alright. It took him some time, but eventually he became a decent reliever for the Reds.

This trade was just gross for both sides, but the edge goes to the Nationals, who were not looking to make the postseason at the time of this trade. The Reds, however, were and they failed. They finished the season 80 - 82, reaching the 80-win-mark for the first time since 2000, but ultimately fell short of the playoffs yet again. Neither side really benefited, but it stings more for the Reds who saw three young players leave town for practically nothing, and without even a postseason appearance to show for it.

Verdict: Three Castellinis

Kyle Lohse

Photo Credit: shgmom56 on Flickr (Original version) UCinternational (Crop), CC BY-SA 2.0 <>, via Wikimedia Commons

SP Zach Ward to the Minnesota Twins for SP Kyle Lohse - July 31, 2006

Okay, okay, I see you, Reds. Way to go bargain-hunting and actually find something worthwhile. Lohse had always been talented, but he struggled with his consistency during his career with Minnesota. Ward was a righty who had just been selected by the Reds with their 3rd-round pick in 2005. He would never reach the majors. Lohse, meanwhile, would begin to look the part of a reliable starter.

This was pretty good! A player who never made it to the big leagues for a real, bonafide MLB starter - that’s how you win a deadline trade! Lohse was never a superstar, but he was a pitcher the team could count on and desperately needed. Although the Reds would miss the playoffs, it was no fault of Lohse, who finished the year with the third-best ERA out of Reds’ starting pitchers.

Verdict: One Castellini

Eddie Guardado

Photo Credit: User Keith Allison on Flickr, CC BY-SA 2.0 <>, via Wikimedia Commons

SP/RP Travis Chick to the Seattle Mariners for RP Eddie Guardado - July 6, 2006

It’s sad how fondly I remember the Eddie Guardado-days. Although, to be fair to myself, he was pretty awesome in 2006. The 35-year-old Guardado arrived in Cincinnati and immediately became the teams’ best reliever. “Everyday Eddie” was an absolute joy.

Chick was a 22-year-old pitcher who would make three appearances for the Mariners in 2006. After that…nada. By 2010, he was out of professional baseball.

Although the Reds ultimately fell short of the postseason, Guardado was a big reason they were able to stay in the hunt as long as they did. Unfortunately, Guardado could not sustain his 2006 production and left the Reds as a free agent in 2008. Still, this is one of the very best trades of the Castellini-era. Guardado came in and was exactly what the Reds needed: a shutdown arm in the bullpen.

Verdict: One Castellini

Matt Maloney

Photo Credit: BubbaFan, CC BY-SA 3.0 <>, via Wikimedia Commons

SP Kyle Lohse to the Philadelphia Phillies for SP/RP Matt Maloney - July 30, 2007

After a run of mediocre-to-pretty-good trades in the Reds’ favor, we get back to the ugliness. As I mentioned previously, Lohse was a solid player for the Reds during his time in Cincinnati. It was a pleasant surprise to see him turn into a reliable starter. It would have been nice to see the Reds flip him for someone who could also turn into a reliable starter.

Despite posting solid numbers at every level of the minor leagues, Maloney, a 23-year-old lefthander, would never find success at the big-league level. After a respectable showing in 2010, when it looked like Maloney might settle into a reliever role, he imploded the following two seasons and was out of the majors by 2012.

This was a very, very disappointing trade. The Reds seemingly identified Lohse as an undervalued player, and he proved their talent-scouts right in their evaluation. Tt was so frustrating to see him leave town for a player who wouldn’t come close to being as impactful. To make matters worse, Lohse would continue to improve as his career progressed, culminating in 2012 with a spectacular season with the St. Louis Cardinals where he went 16-3 and finished 7th in the NL Cy Young-voting. Do you think the Reds could have used that, huh?

Verdict: Four Castellinis

Nick Masset

Photo Credit: Keith Allison on Flickr, CC BY-SA 2.0 <>, via Wikimedia Commons

CF Ken Griffey Jr. to the Chicago White Sox for RP Nick Masset & INF Danny Richar - July 31, 2008

The end of an era. When Griffey Jr. arrived in Cincinnati, it was like the Beatles were in town. “The Kid” was coming home.

Injuries ruined the homecoming. In eight seasons with the Reds, Griffey Jr. would only play more than 140 games three times. After being such an unbelievable player in Seattle (they made a video game called Major League Baseball featuring Ken Griffey Jr. back in 1998), Griffey would fall to near irrelevance in Cincinnati.

Still, he was a beloved member of the Cincinnati community. He was the hometown kid. It hurt to see him leave with so much unfulfilled, even if all the promise of his arrival had been spoiled by time. Even though the White Sox would go on to lose in the AL Divisional Series, it was nice to see Griffey Jr. get a chance to add that one missing piece from his impeccable resume: a World Series ring.

As for the Reds, they finally managed to fleece a competent ballplayer in exchange for an aging veteran. Although Richar was not a contributor, Masset was a good player in Cincinnati, which is a lot more than can be said about many of the players the Reds have acquired in trades over the years. This is more what a deadline deal should look like.

Verdict: Two Castellinis

Scott Rolen

Photo Credit: Keith Allison on Flickr, CC BY-SA 2.0 <>, via Wikimedia Commons

3B Edwin Encarnacion, Josh Roenicke & Zach Stewart to the Toronto Blue Jays for Scott Rolen - July 31, 2009

This one is rough, but it didn’t look that bad at the time. In fact, I remember being very excited about it. Unfortunately, hindsight is a real eye-opener.

The Reds were looking to make the playoffs in 2009, and they made a splash at the deadline, acquiring a borderline Hall of Famer in the 34-year-old Rolen. In the short-term, it worked.

The Reds would go on to have their best season in ages in 2010, winning the NL Central. Rolen would appear on his sixth All-Star team and win his eighth Gold Glove. Everything was just hunky-dory in Cincinnati.

However, something was brewing across the border in the tundras of Canada (okay, okay, Toronto is actually a pretty nice place). Encarnacion had always been talented, but he started putting it all together with the Blue Jays. By 2012, Encarnacion had turned himself into a 40 HR-guy. In 2015 and 2016, Encarnacion teamed with Jose Bautista and Josh Donaldson to form one of the most potent lineups in the MLB, and helped the Blue Jays reach back-to-back AL Championship Series.

So…the Blue Jays won this trade. Yes, the two other players they received in the Rolen-trade basically amounted to nothing, but when the centerpiece turns out to be one of the most feared sluggers this century, who cares? Rolen, meanwhile, would start to fall apart by 2011. One can only imagine the damage a Reds’ lineup with Encarnacion, Joey Votto, Jay Bruce and Todd Frazier could have inflicted on opposing pitchers. It wasn’t a bad trade for the Reds, all things considered, but it’s tough to be a winner when you let someone like Encarnacion walk out the door.

Verdict: Three Castellinis

Jonathan Broxton

Photo Credit: Keith Allison on Flickr, CC BY-SA 2.0 <>, via Wikimedia Commons

SP Juan Carlos Sulbaran and RP Donnie Joseph to the Kansas City Royals for RP Jonathan Broxton - July 31, 2012

This one worked out nicely. No matter what year, no matter what team, pitching depth is always a concern for contenders at the deadline, especially in the bullpen. Broxton turned out to be exactly the player the Reds were looking for in 2012.

Despite featuring a rotation with four pitchers who crossed the 200-inning threshold, and a closer in Aroldis Chapman that set all-time records for pitch velocity, the Reds were a little thin between the starters and the finisher. Enter Broxton, a former All-Star closer with the Los Angeles Dodgers. Broxton made his presence felt immediately, forming a wonderful lefty/righty-tandem with Sean Marshall.

As for Sulbaran and Joseph, neither prospect turned into a contributor for the Royals. A 22-year-old righthander, Sulbaran would never reach the majors in his career. Joseph, a former 3rd-round pick of the Reds in 2009, would play two seasons with the Royals in 2013 and 2014, allowing 6 ERs in 6.1 IP in total.

Definite win for the Redlegs. Broxton was brought in to fill a specific role, and he did just that. The Reds may have blown their playoff series versus the San Francisco Giants, but that was no fault of Broxton, who gave the Reds everything they could ask for in three scoreless appearances. Throw in the fact that neither prospect the Reds gave up turned into valuable pros, and you have a recipe for a successful trade.

Verdict: One Castellini

Johnny Cueto

Photo Credit: Keith Allison on Flickr, CC BY-SA 2.0 <>, via Wikimedia Commons

SP Johnny Cueto to the Kansas City Royals for SP Brandon Finnegan, SP Cody Reed & SP John Lamb - July 26, 2015

Okay, so apparently, it’s hard to fleece the Royals twice. Lesson learned.

It was a dark day in Reds’ history when Johnny Cueto left town. He was a workhorse, he was entertaining as hell, and he was our homegrown guy. In 2012, he won 19 games. In 2014, he won 20. And all of a sudden, he was gone.

After a run of successful seasons, the Reds bottomed out in 2015. At the deadline, they looked to trade their best chip for a massive haul. At the time, it seemed like they nailed it.

Although they would never find success at the MLB-level, Finnegan, Reed, and Lamb were all highly regarded prospects by the baseball community. Each, at one point, was named to Baseball America’s Top 100 prospects list. For Reds fans, this trade was a reminder that prospect rankings don’t mean squat.

It doesn’t get any worse than this. The Reds traded their ace for basically nothing. None of the players they got back could make an impact for the team and none are playing in the majors right now.

To pour more salt in the wound, Cueto is still pitching in the majors with the Chicago White Sox. Oh yeah, and the year of the trade, the Royals won the World Series with Cueto. This move set the Reds back years.

Verdict: Five Castellinis

Mike Leake

Photo Credit: Keith Allison from Hanover, MD, USA, CC BY-SA 2.0 <>, via Wikimedia Commons

SP Mike Leake to the San Francisco Giants for OF Adam Duvall & SP Keury Mella - July 30, 2015

Another homegrown starter on his way out of Cincinnati at the trade deadline. After an excellent career at Arizona State, Leake would be drafted by the Reds with the #7 pick in the 2000 MLB Draft. Less than a year later, he was in the Reds’ MLB rotation. Talk about being on baseball’s version of a rocket ship.

As he settled in at the majors, Leake became a dependable starting pitcher. He was also good with the bat (for a pitcher), knocking in five HRs during his Reds' tenure. Leake was a fun player

With the Reds in the middle of a collapse in 2015, Leake was traded to the San Francisco Giants to help jump-start the next rebuild. In return for the 27-year-old Leake, the Reds acquired Mella, a 21-year-old righthander, and Duvall, a 26-year-old outfielder.

Mella was the star of the package, having appeared in the All-Star Futures Game that season. Despite his talent, Mella never figured out MLB hitters, appearing in just 21 games over a five-year MLB career. Duvall was a throw-in, but he’d go on to be the better of the two.

This one feels pretty “meh,” but slightly favors the Reds because Duvall not only turned into a productive player, but he also turned into another trade chip (more on that in a bit) down the road. Leake was a solid player for the Reds, but he never pitched quite as well after leaving Cincinnati. He has been out of the MLB since 2020.

Verdict: Two Castellinis

Jay Bruce

Photo Credit: Blackngold29, CC0, via Wikimedia Commons

RF Jay Bruce to New York Mets for SP Max Wotell & 2B Dilson Herrera - August 1, 2016

Another casualty of the Reds’ rebuild attempt, Bruce was another tough loss to suffer for Reds fans. After a rough 2015 season, the Reds followed up with another stinky start, going 41 - 62 up to the trade deadline, a whopping 21.0 games out of first place.

A former top prospect of the Reds, Bruce was a three-time All-Star, having won back-to-back Silver Slugger awards in 2012 and 2013. The powerful Bruce was always a force in the middle of the Reds’ lineup - when he was on, that is. When he was off, Bruce was really off. His slumps were legendary. But when he was hot, he could be a wildfire.

As for the Reds’ return, Wotell would never reach above A-ball with the Reds and was out of professional baseball by 2019, while Herrara lasted a little longer, but by 2019, he too was no longer in the Reds’ organization. Per usual, the Reds were able to get rid of an aging veteran at an opportune time, as Bruce would not be on a big-league roster in five years. But also, per usual, the Reds didn’t get any useful players. This is why Reds fans have trust issues.

Verdict: Four Castellinis

Adam Duvall

Photo Credit: NewJack984, CC BY-SA 4.0 <>, via Wikimedia Commons

OF Adam Duvall to the Atlanta Braves for RP Lucas Sims, OF Preston Tucker & SP/RP Matt Wisler - July 30, 2018

The Adam Duvall-saga comes full circle. Exactly three years to the day, the same way he arrived, Duvall left town on a trade-deadline-deal to the eventual NL East winners, the Atlanta Braves.

Duvall, as I mentioned earlier, turned into a fine player with the Cincinnati Reds - maybe the Ohio River was able to channel the innate power in his swing? After struggling to break into the majors, Duvall settled in as an everyday outfielder with some pop. However, after productive seasons in 2016 and 2017, Duvall regressed badly in 2018.

So, at the time, it seemed like a pretty strong move to get something in return for the 29-year-old slugger. But to get three prospects in return was eye-opening. Throw in the fact that Duvall would spend much of his time in 2018 with the Braves’ AAA squad, and it seemed pretty clear that the Reds were big winners in this one. Time has a way of changing our perspective, however, and this trade is a perfect example.

As for the three players the Reds received? Today, just one, Sims, remains in the organization. Tucker’s contract was purchased by the Braves barely a month later and he returned to Atlanta. Wisler flashed at times with the Reds but was ultimately traded. In typical fashion, Wisler has settled-in to a role as set-up man with the Tampa Bay Rays and is currently in the middle of the best season of his career.

Perfectly average sums up this trade. The Reds, per usual, found a way to move a declining veteran at the deadline, although in Duvall’s case, the apparent decline may have been an aberration. Still, getting three players in return for a player you got as a throw-in on a trade three years ago is pretty good, all things considered. Duvall was never going to be a long-term option for the Reds. Even though only Sims remains, these are the kinds of trades a rebuilding team needs to make.

Verdict: Two Castellinis

Photo Credit: Arturo Pardavila III from Hoboken, NJ, USA, CC BY 2.0 <>, via Wikimedia Commons

OF Yasiel Puig to the Cleveland Indians/Guardians for SP Trevor Bauer - July 31, 2019

Maybe the biggest needle-mover of all the Reds’ trade deadline deals of the Castellini-era, Puig arrived in Cincinnati after a massive trade in the offseason with the Los Angeles Dodgers that saw the Reds finally unload Homer Bailey and his massive contract. Upon arriving in the Queen City, Puig, who said red was his favorite color, immediately became a fan-favorite, endearing himself to the Reds’ base by instigating multiple brawls with the division-rival Pittsburgh Pirates and flashing his early-career form. El Guerrero Rojo’s time in Cincinnati was short as the Reds, under first-year general manager Nick Krall, made a deadline-swing.

To be clear, this trade involved many more players than just Puig and Bauer, and also included a third team, the San Diego Padres. To save time, I’m going to mention these players briefly: from the Reds, Puig and Scott Moss went to the Indians/Guardians, and Taylor Trammell went to the Padres; from the Indians/Guardians, Bauer went to the Reds; from the Padres, Victor Nova, Logan Allen and Franmil Reyes went to the Indians/Guardians. Given how none of these other involved players went on to accomplish much of anything in the majors, you really get a feel for what a crapshoot prospect-trades can really be.

So now, the Reds had their ace - at least, that’s what they hoped. Ever since he was selected with the #3 pick in the 2011 draft by the Arizona Diamondbacks, Bauer was considered an extremely talented player. In his six full seasons prior to the trade, Bauer demonstrated that elite ability, but also struggled with inconsistency and had a reputation for being a locker-room malcontent.

He often clashed with teammates, including reportedly ignoring his catcher’s signals during his time in Arizona. He rubbed a lot of his coaches the wrong way. He was combative on social media with fans and detractors. In the end, it was too much for Cleveland.

Bauer didn’t acclimate to Cincinnati right away, but the following year would be Bauer’s finest as a professional. In the COVID-shortened 2020 season, Bauer dominated from the onset, going 5-4 in 11 starts with an NL-leading 1.73 EA, winning the NL Cy Young award, the first time a Reds’ pitcher won the award in the history of the franchise. It was the coming-out-party everyone had been waiting for, and for Bauer, it was time to cash in.

Now a free agent, Bauer would sign a massive 3-year, $102 million contract with the Los Angeles Dodgers in the offseason, becoming one of the highest-paid athletes in America. Then everything fell apart.

As I mentioned previously, Bauer has never been an easy person to get along with. Well, I guess that goes for his private life too. On July 2, 2021, the MLB placed Bauer on administrative leave after sexual assault allegations surfaced. After being on paid-leave through the remainder of the 2021 season, the MLB handed down an unprecedented 324 game suspension, effectively two full seasons. Bauer has maintained his innocence throughout the process and is appealing the suspension, in addition to bringing a defamation lawsuit against the sports media websites Deadspin and The Athletic, as well as one of The Athletic’s former reporters, Bauer’s accuser, and one of her attorneys.

As of today, there are now three separate sexual assault allegations, with no resolution in sight. But hey, at least this is the Dodgers’ problem and not the Reds’, right?

I don’t feel good about giving the Reds plus marks here, but they kinda nailed this one. Bauer may be a slimy guy, but he had an amazing season for the Reds in 2020 and being the first Red to win the Cy Young is a big deal for baseball’s oldest franchise. Puig, meanwhile, hasn’t played in the MLB since the end of the 2019 season. So, even though the Reds couldn’t retain Bauer (and thank goodness for that), they still managed to squeeze every last drop of talent and production out of him. Props to you, Reds.

Verdict: One Castellini

Scooter Gennett

Photo Credit: Jeff Warrington on Flickr (Original version), CC BY 2.0 <>, via Wikimedia Commons

INF Scooter Gennett to Giants for a Player to be Named Later - July 31, 2019

This is the last one on our list, and I saved one of the best for last. Scooter, oh Scooter. You were an awesome story. When you become just the 17th person to hit four home runs in a single game, and you do it in a Reds uniform, you instantly become a franchise-icon. Okay, icon is a little strong, but still…that was good stuff.

A former second baseman with the Milwaukee Brewers, Gennett found a home in Cincinnati as a utility player. Over two seasons with the Reds from 2017-18, Gennett batted .303 and averaged 25 HRs per season, making appearances at first base, second base, third base, right field and left field. He even made the All-Star team in 2018.

Unfortunately, Gennett was unable to maintain that production, and he fell off considerably in the 2019 season. After dealing with a groin strain to start the season and struggling to the tune of a .217 BA and zero home runs, Gennett was dealt to the Giants at the trade deadline. The 29-year-old failed to make much of an impact. Since 2019, Gennett has not made an appearance in the majors.

So…about that player to be named later…did I forget to mention the Reds never received a player? That’s correct. As far as I can tell (and I looked into this significantly), the Reds never got a player back as a result of this trade. I don’t know if that’s because if Gennett performed so poorly that the Giants don’t have to send someone back, or if the Reds simply forgot or don’t care, but either way, there’s no record of anyone from the Giants’ organization coming to Cincinnati as a result of this trade. I had no idea this was even possible.

Still, the Reds get some credit for unloading Gennett when he was about to hit a wall. Trading him to the Giants for nothing is no different that releasing him outright - and that option was probably also on the table. I can’t make the Reds winners (or even tie-ers), but this trade isn’t that bad…even if they never got a player back.

Verdict: Three Castellinis

10 views0 comments


bottom of page