Biggest Regrets From the 2022 MLB Trade Deadline

Kerry Miller@@kerrancejamesFeatured Columnist IVSeptember 17, 2022

Biggest Regrets From the 2022 MLB Trade Deadline

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    NEW YORK, NY - JULY 31: Jordan Montgomery #47 of the New York Yankees pitches against the Kansas City Royals during the first inning at Yankee Stadium on July 31, 2022 in the Bronx borough of New York City. (Photo by Adam Hunger/Getty Images)
    Why oh why did the Yankees let Jordan Montgomery go? (Adam Hunger/Getty Images)

    Pretty much every Major League Baseball team regrets something it did or did not do at the trade deadline on August 2.

    But some of those regrets are bigger than others.

    Could the New York Mets and Chicago White Sox have done more to improve their rosters ahead of the deadline? Absolutely. But their crosstown rivals are on this list for two trades that haven't panned out (Yankees) and a non-trade that never made sense to any of us (Cubs).

    For the most part, we'll be focused on teams that at least had a postseason pulse when the deadline hit. However, we'll start out with a team that didn't even have a realistic shot at the playoffs on Opening Day.

    And we'll wrap things up with my biggest regret from the trade deadline.

    All statistics and records current through the start of play on Friday, Sept. 16.

Oakland A's: Not Trading Away Elvis Andrus and Sean Murphy

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    OAKLAND, CALIFORNIA - SEPTEMBER 11: Sean Murphy #12 of the Oakland Athletics bats against the Chicago White Sox in the bottom of the first inning at RingCentral Coliseum on September 11, 2022 in Oakland, California. (Photo by Thearon W. Henderson/Getty Images)
    Sean Murphy (Thearon W. Henderson/Getty Images)

    The Elvis Andrus part of it I can understand, as there probably weren't many suitors for a $7 million 33-year-old shortstop with minimal pop and a sub-.300 on-base percentage dating back to the start of 2020. Didn't help matters that his contract included a $15 million player option for 2023 if he reached 550 plate appearances this season, which he was/is roughly on pace to do.

    But they surely could have gotten something for him if they were willing to eat the rest of his 2022 salary just to have him play somewhere else—which they were clearly willing to do, because they designated him for assignment two weeks after the trade deadline. The Chicago White Sox scooped him up for basically nothing and he has been thriving in Tim Anderson's stead, batting .308 with six home runs.

    The Sean Murphy part is less understandable, because he is clearly a player with a lot of value which the A's could have turned into prospects—which has more or less been their entire goal for the past calendar year of rebuilding.

    The 27-year-old catcher is making $725,000 this season and is arbitration-eligible through each of the next three seasons. And he's quite good. He hit 17 home runs and won a Gold Glove last season. This year, he's batting .253 with 18 home runs. He's clearly a player any team actually trying to win baseball games would love to have under its control through the end of 2025.

    At any other position, it would make sense for the A's to just hang onto this asset and hope to become competitive again before he hits free agency. But, per's prospect rankings, three of the top five players in Oakland's farm system are catchers. And they even called up the top guy on that list, Shea Langeliers, when they waived Andrus.

    Selling Murphy for a platter of prospects was the obvious move here, and it became an even bigger whiff by Oakland when the Cubs ended up not trading Willson Contreras. Murphy would've been the best backstop available and would have been quite valuable on the trade block.

Milwaukee Brewers: Trading Away Josh Hader

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    SEATTLE, WASHINGTON - SEPTEMBER 13: Josh Hader #71 of the San Diego Padres pitches during the ninth inning against the Seattle Mariners at T-Mobile Park on September 13, 2022 in Seattle, Washington. (Photo by Steph Chambers/Getty Images)
    Josh Hader (Steph Chambers/Getty Images)

    From July 4 through July 29 in Milwaukee, Josh Hader had a 14.04 ERA. And that got even worse after he landed in San Diego, where he had a 23.14 ERA through his first four weeks.

    Hard to believe this was the same flame-throwing lefty who opened the season with 18 consecutive scoreless appearances, recording a save in each one of them. For a little while there, it looked like Milwaukee actually hit the jackpot for extracting any return on investment for a guy who was about to Rick Ankiel his way out of a pitching career.

    But Hader seems to have figured things out recently.

    Over the course of his last five appearances, the former Brewers/current Padres closer has a line of 5.0 IP, 2 H, 1 ER, 1 BB, 6 K with three successful saves. While that's not quite the strikeout rate we've grown accustomed to seeing from him in his MLB career, at least he has stopped giving up runs left and right.

    And what Milwaukee got in exchange for Hader—who still has one year of team control remaining, no less—wasn't much.

    The Brewers have already waived Dinelson Lamet. Taylor Rogers has been serviceable, but he's not even the closer and he's a free agent after this season. As was the case while he was in San Diego's system, Esteury Ruiz has looked fantastic in the minors but can't seem to get that to convert to hitting at the MLB level. And while Robert Gasser has some promise as a left-handed starting pitcher, we'll have to wait and see if that eventually translates to Triple-A, let alone the majors.

    The real reason Milwaukee regrets trading away Hader, though, is that it seemed to fracture the clubhouse. The Brewers were 57-45 and had a three-game lead in the NL Central at the end of July, but they have gone 19-22 since dealing their four-time All-Star closer, have lost all hope of winning the division and probably won't make the playoffs at all—unless, ironically, Hader starts blowing saves for the Padres again and San Diego falls out of contention.

New York Yankees: Replacing Jordan Montgomery with Frankie Montas

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    NEW YORK, NEW YORK - SEPTEMBER 09:  Frankie Montas #47 of the New York Yankees pitches during the first inning against the Tampa Bay Rays at Yankee Stadium on September 09, 2022 in the Bronx borough of New York City. (Photo by Jim McIsaac/Getty Images)
    Frankie Montas (Jim McIsaac/Getty Images)

    At the time, this seemed like a no-brainer move for the Yankees.

    Frankie Montas was one of the best players available at this year's trade deadline, both because of how consistently well he had pitched in Oakland (aside from a rough few starts in 2020) and because he's under team control through next season. Giving up a quartet of prospects—even four good ones—for Montas and another pitcher under team control through 2024 (Lou Trivino) made perfect sense for a team trying to win it all right now.

    But (Pt. I) Montas has not fared well in New York. He did have one impressive start in a critical game against the Rays earlier this month, but he entered Friday with a 5.94 ERA and 1.46 WHIP through his first seven starts. If the postseason began today, he probably wouldn't be in New York's four-man starting rotation.

    And (Pt. II) after getting Montas, the Yankees sent the suddenly expendable Jordan Montgomery to St. Louis in exchange for outfielder Harrison Bader. While Bader has yet to make his pinstripes debut while on the IL, Montgomery has pitched like a Cy Young candidate. He has made eight starts with a 2.05 ERA, including five shutout innings against the Yankees when the Cardinals swept that series in early August.

    At least the Trivino portion of the trade has worked out nicely for the Yankees. After racking up a 6.47 ERA this season with the A's, he has made 18 appearances with a 1.20 ERA. He has been used almost exclusively in low-leverage situations with New York, but that might change if he keeps this up.

Minnesota Twins: Giving Up a Bunch of Prospects for Jorge López and Tyler Mahle

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    CHICAGO, ILLINOIS - SEPTEMBER 03: Tyler Mahle #51 of the Minnesota Twins pitches against the Chicago White Sox in the first inning at Guaranteed Rate Field on September 03, 2022 in Chicago, Illinois. (Photo by Chase Agnello-Dean/Getty Images)
    Tyler Mahle (Chase Agnello-Dean/Getty Images)

    All told, the Minnesota Twins gave up seven prospects to bring in starting pitcher Tyler Mahle from Cincinnati and relief pitcher Jorge López from Baltimore.

    Not all top prospects, of course. And at least they didn't part with Royce Lewis or Emmanuel Rodriguez. But they didn't exactly give away a platter of nothing. Infielder Spencer Steer (to the Reds) is the most intriguing of the bunch, with pitcher Cade Povich (to the Orioles) and corner infielder Christian Encarnacion-Strand (to the Reds) each likely to be in the majors before too long.

    And what did they end up getting in return?

    A starter with a 4.41 ERA who is already on the IL for the second time since joining the Twins and a closer with a 4.11 ERA who has blown two of his six save chances.

    Not terrible, but not ideal. And as a result, the Twins—who were six games over .500 and a game up in the AL Central heading into the trade deadline—have gone 18-22 dating back to August 2 and almost need to go 4-1 in this five-game road series against the Guardians to have any realistic hope of making the playoffs.

    On the plus side, Mahle and López are not two-month rentals. Minnesota was willing to part with as much as it did because Mahle may well be the ace of this rotation in 2023, and because López is under team control through 2024. But, you know, the Twins were also hoping those two additions would help guide them to the postseason this year, and that's not looking promising.

Toronto Blue Jays: Trading for Whit Merrifield

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    BALTIMORE, MARYLAND - SEPTEMBER 06: Whit Merrifield #1 of the Toronto Blue Jays reacts after striking out against the Baltimore Orioles during the second inning at Oriole Park at Camden Yards on September 06, 2022 in Baltimore, Maryland. (Photo by Patrick Smith/Getty Images)
    Whit Merrifield (Patrick Smith/Getty Images)

    From 2017 to '21, Whit Merrifield had a rock-solid run in Kansas City. The two-time All-Star batted .292 and slugged .439 with 66 home runs and 151 stolen bases.

    But that guy never showed up this season.

    Through the end of July, Merrifield was batting .240 with a .346 slugging percentage. And after stealing 40 bases in 2021, he was on pace for around 25 this year.

    Toronto was optimistic that a change of scenery and a shift to playing in games that actually matter would snap Merrifield out of his funk, but that certainly hasn't been the case.

    If anything, that pressure has only made him struggle more.

    Through 29 games with the Blue Jays, he's batting an even .200 with just two extra-base hits and one stolen base. Even with Lourdes Gurriel Jr. on the IL for the past week, Merrifield has only logged a complete game in two of Toronto's last 21 contests, more or less entrenched in a platoon situation with Raimel Tapia.

    The good news is they didn't part with that much to get him. Neither Max Castillo nor Samad Taylor ranks top 10 in the Royals' farm system, per, though they do both rank in Kansas City's top 30.

    The bad news is they'll owe Merrifield $6.75 million for 2023, which is the real sunk cost in the equation. The Jays almost have to keep giving him reps this season in anticipation of needing him again next year.

Cubs, Giants and Red Sox: Not Getting Something for Impending Free Agents

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    CHICAGO, IL - AUGUST 20:  Willson Contreras #40 of the Chicago Cubs celebrates while rounding the bases after hitting a two-run home run in the fifth inning against the Milwaukee Brewers at Wrigley Field on August 20, 2022 in Chicago, Illinois.  (Photo by Jamie Sabau/Getty Images)
    Chicago's Willson Contreras (Jamie Sabau/Getty Images)

    Chicago's decision not to part with three-time All-Star catcher Willson Contreras was the most befuddling non-move of them all. His departure from the North Side seemed like a foregone conclusion for months, yet the deadline came and went, and there he sat on a team 19 games below .500.

    If they are ultimately able to re-sign him this offseason, great. At that point, the move will feel like less of a mistake. But what they should have done was what the Rockies did with Daniel Bard, working out that extension prior to the deadline rather than risk watching Contreras walk away for nothing at the end of the year.

    At least Boston and San Francisco were still reasonably in the playoff hunt when they decided to just let it ride with their impending free agents, but they also really should have embraced selling while they could.

    Boston was 52-52 and three games back in the AL wild-card standings with J.D. Martinez, Nathan Eovaldi, Michael Wacha and Rich Hill among their players not under contract beyond this season. There's also Xander Bogaerts, who is likely to decline the player option that would keep him in Boston for four more years. The Red Sox could have had a full-blown fire sale, but aside from sending Christian Vázquez to Houston, they basically did nothing. They have since gone 17-22 and now have no hope of reaching the postseason.

    Similar situation for San Francisco, which was sitting at 51-52 and 4.5 games out of the NL's wild-card picture. Joc Pederson is a free agent after this season, and Carlos Rodón is all but certain to decline his one-year player option in pursuit of a long-term deal. Rodón, in particular, would have been a coveted asset on the trade block, but Pederson's slugging would have also generated a fair amount of interest. But the Giants instead made a bunch of meaningless moves, neither committed to buying nor selling. They have gone 18-22 since then, also dropping hopelessly out of the postseason conversation.

Me: Relentlessly Bashing the Orioles for Trading Away Trey Mancini and Jorge López

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    HOUSTON, TEXAS - AUGUST 26: Trey Mancini #26 of the Houston Astros flies out to right field during the fifth inning against the Baltimore Orioles at Minute Maid Park on August 26, 2022 in Houston, Texas. (Photo by Carmen Mandato/Getty Images)
    Trey Mancini (Carmen Mandato/Getty Images)

    On the morning of the trade deadline, the Baltimore Orioles were 52-51 and 2.5 games back for the American League's final wild-card spot. Even though reaching the postseason was unlikely, I think I speak for the majority of baseball fans when I say it would have been great to see them go for it, given how awful they had been over the past half decade.

    Instead, they embraced more of a seller mindset, sending 1B/OF Trey Mancini (who has a $10 million mutual option for next season that Baltimore was unlikely to exercise) to Houston in exchange for two Single-A pitchers and shipping closer Jorge López to Minnesota for a quartet of prospects.

    It was disappointing to see.

    The O's were playing with house money, and instead of going out and getting an inexpensive starting pitcher (perhaps José Quintana and/or Mitch White) to improve their chances of making the playoffs, it looked like they opted to just pack it in and prepare for a more legitimate run in 2023 or 2024.

    Six weeks later, however, those moves look brilliant, leaving egg on the face of everyone (including myself) who criticized Baltimore for its deadline decisions.

    As previously noted, López (who had a 1.68 ERA this season with the Orioles) has a 4.11 ERA in Minnesota and has converted just four of six save chances. And after looking solid for his first two weeks in Houston, Mancini is triple-slashing .174/.294/.361 over his last 26 games with the Astros.

    Moreover, Baltimore is doing just fine without them. Rookie Félix Bautista is thriving in the closer role with a 1.45 ERA and a 10-for-10 mark in save chances since the deadline. Gunnar Henderson is batting .320 since making his MLB debut at the end of August. And the Orioles have gone 23-16 since the beginning of August.

    However, Seattle has been even better during that time (25-13), so the O's are now 4.5 games out of the wild-card picture. But it's not like they were going to go 30-9 by hanging onto Mancini and López. They're arguably better than they were six weeks ago, and they are better positioned for future success. Bravo. And I'm sorry for doubting you.


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