The Biggest Regret Each MLB Team Should Have This Offseason

Joel Reuter@JoelReuterBRFeatured ColumnistFebruary 7, 2020

The Biggest Regret Each MLB Team Should Have This Offseason

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    Mike Stobe/Getty Images

    It's never too early to second-guess how MLB teams chose to approach the offseason.

    Whether it was a questionable free-agent signing, a trade chip that was not fully utilized or a hole on the roster that went unaddressed, all 30 teams have at least one thing they could wind up regretting.

    There's still time for some of these issues to be ironed out before Opening Day, but in many cases, the presumptive damage is already done.

    Let's dive right into each MLB team's biggest potential regret of the 2019-20 offseason.

AL East

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    Tommy Pham
    Tommy PhamJulio Aguilar/Getty Images

    Baltimore Orioles: Failing to Maximize Trade Chips

    The rebuilding O's were thin on viable trade chips heading into the offseason, but the cupboard was not bare. Speedy infielder Jonathan Villar, starter Dylan Bundy and reliever Mychal Givens have all seen their names mentioned in trade rumors in the past.

    The front office did flip Villar and Bundy, but the returns were less than stellar. The best prospect acquired in either deal was right-hander Kyle Bradish, who now ranks as Baltimore's No. 26 prospect, according to


    Boston Red Sox: Failing to Address the Bullpen

    The Mookie Betts trade is the headlining move of the offseason and will be dissected for years to come, but the Red Sox's failure to properly address a weak relief corps could prove to be their biggest regret in 2020.

    The Red Sox finished 18th in bullpen ERA (4.40) last season while tying for the MLB lead with 31 blown saves. Boston acquired Austin Brice (via MIA) and Jeffrey Springs (via TEX) in trades, but those are the only relievers who have been added to the 40-man roster, and neither is a lock to win an Opening Day spot.


    New York Yankees: Failing to Add Starting Pitching Depth

    The addition of Gerrit Cole on a massive nine-year, $324 million deal made an already stacked Yankees squad the team to beat in some people's minds.

    However, the starting rotation remains a question mark. MLB suspended Domingo German for 81 games in January, and the Yankees just announced that James Paxton will be sidelined three to four months following back surgery. That leaves J.A. Happ and Jordan Montgomery both penciled into rotation spots, and the Yankees perhaps regretting not adding a back-of-the-rotation arm.


    Tampa Bay Rays: Trading OF Tommy Pham

    On Dec. 6, the Rays shipped Tommy Pham and two-way prospect Jake Cronenworth to the San Diego Padres in exchange for Hunter Renfroe, Xavier Edwards and a player to be named later.

    The addition of Edwards could pay considerable long-term dividends, but in the short term, it's hard to argue the Pham-for-Renfroe move is anything but a downgrade. Coming off a 96-win season and well-positioned to contend once again, the Rays should be focused on fielding the best possible team in 2020.


    Toronto Blue Jays: Signing SP Hyun-Jin Ryu to a 4-Year Deal

    Prior to a stellar 2019 season that saw him finish second in NL Cy Young voting, Hyun-Jin Ryu had not eclipsed the 130-inning mark since 2014.

    The left-hander will turn 33 years old next month, and given his injury history, a four-year deal comes with considerable risk. The Blue Jays are a young team on the rise, and he immediately becomes the ace of the staff, but it's easy to envision this deal could become one the front office regrets.

AL Central

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    Corey Kluber
    Corey KluberMark Brown/Getty Images

    Chicago White Sox: Trading Prospect Steele Walker

    Former top prospect Nomar Mazara was an intriguing buy-low target on the offseason trade market. The up-and-coming White Sox jumped at the opportunity to acquire him from the Texas Rangers and upgrade an underperforming right field position.

    However, parting with 2018 second-round pick Steele Walker was a steep price to pay. The University of Oklahoma standout hit .284/.361/.451 with 51 extra-base hits in 120 games between Single-A and High-A in his first full pro season. With the ability to man center field, he has a chance to be an impact MLB player in the near future.


    Cleveland Indians: Trading SP Corey Kluber

    Corey Kluber started just seven games last season and struggled to a 5.80 ERA before suffering a fractured forearm that ended his season in May. However, in the five seasons prior, he was one of baseball's truly elite starters, posting a 2.85 ERA and 1.02 WHIP while averaging 246 strikeouts and 218 innings per year.

    As the Indians continue to pinch pennies, his $17.5 million salary for 2020 was deemed too expensive, and they traded him to the Rangers for fourth outfielder Delino DeShields and hard-throwing reliever Emmanuel Clase. It's hard to believe that's all they could get for the two-time Cy Young winner. Holding on to him until midseason and giving him the chance to prove he was healthy might have been the better move.


    Detroit Tigers: Failing to Find a Trade Partner for SP Matthew Boyd

    The Tigers probably missed their chance to sell Matthew Boyd at peak value when he stayed put at the trade deadline this past summer. He stumbled to a 6.11 ERA in 10 starts over the final two months of the season, undermining what was otherwise a breakout season.

    The left-hander still finished with 238 strikeouts in a career-high 185.1 innings, and his three remaining years of club control gave him plenty of appeal on the offseason trade market. However, the 29-year-old has stayed put in Detroit this offseason, and the door could close on netting a significant return if he struggles to begin 2020.


    Kansas City Royals: Holding on to Their Trade Chips

    The Royals could have eaten some of Ian Kennedy's remaining salary to facilitate a trade. They could have done the same with left-hander Danny Duffy. They could have even tested the market on 2019 standouts Hunter Dozier and Jorge Soler to see if it was worth flipping them in the early stages of a rebuild that could take several years.

    Instead, they have settled for a handful of under-the-radar signings while failing to add any more young, controllable talent to the organization this winter. Does the front office think the Royals are closer to contention than they appear at surface level?


    Minnesota Twins: Not Adding a Late-Inning Reliever

    Despite finishing 10th in the majors with a 4.17 bullpen ERA, the Twins spent a good chunk of 2019 piecing together the relief corps ahead of setup man-turned-closer Taylor Rogers.

    They re-signed deadline addition Sergio Romo to a one-year, $5 million deal that includes a 2021 club option. They also inked Tyler Clippard to a one-year, $2.75 million pact. But those have been the only notable additions to the bullpen. Can in-house guys like Trevor May, Tyler Duffey and Zack Littell duplicate last year's success?

AL West

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    Blake Treinen
    Blake TreinenMichael Zagaris/Getty Images

    Houston Astros: Relying on In-House Rotation Replacements

    The Astros lost Gerrit Cole (212.1 IP, 2.50 ERA, 326 K) and Wade Miley (167.1 IP, 3.98 ERA, 140 K) to free agency this offseason, and they didn't make any significant outside additions to replace them.

    As it stands, injury returnee Lance McCullers Jr., rookie Jose Urquidy and swingman Brad Peacock are projected to round out the starting rotation behind Justin Verlander and Zack Greinke, according to Roster Resource. A reunion with Miley or a similar mid-level signing would have been in the team's best interest.


    Los Angeles Angels: Failing to Add a Front-Line Starting Pitcher

    Adding Anthony Rendon and Jason Castro in free agency and trading for Joc Pederson, along with the impending arrival of top prospect Jo Adell, could give the Angels an offensive juggernaut in 2020. The question, as has been the case in recent years, is the starting rotation.

    Julio Teheran signed a one-year, $9 million deal, and both Dylan Bundy (via BAL) and Ross Stripling (via LAD) were acquired in trades, but the Angels still lack a true staff ace. Instead, they will be counting on a collection of No. 3/4-starter types to lead the team to its first postseason appearance since 2014.


    Oakland Athletics: Non-Tendering RP Blake Treinen

    After a disappointing 2019 season relative to his stellar 2018 campaign, Blake Treinen was non-tendered by the Athletics at the start of the offseason when his projected $7.8 million arbitration salary was deemed too steep by the small-market club.

    The Dodgers signed him to a one-year, $10 million deal, so the decision worked out well for Treinen, and there's a good chance the A's will wind up regretting the cost-cutting move. The 31-year-old is just a year removed from posting a 0.78 ERA and 11.2 strikeouts per nine innings while converting 38 of 43 save chances.


    Seattle Mariners: Not Finding a Trade Partner for 3B Kyle Seager

    Kyle Seager posted a career-low 86 OPS+ in 2018 and then missed the first 53 games of the 2019 season recovering from hand surgery. Once he returned to action and shook off the inevitable rust, he finished strong to post an .895 OPS with 10 doubles, 14 home runs and 38 RBI in 214 plate appearances over the final two months.

    It appeared that might open the door for an offseason trade, perhaps as a consolation prize to teams that missed out on Anthony Rendon and Josh Donaldson, but no deal was made. The $38 million he is owed over the next two years was no doubt a prohibiting factor.


    Texas Rangers: Not adding a Proven Center Fielder

    With Delino DeShields now in Cleveland, the Rangers do not have a proven center fielder on the roster.

    Joey Gallo (38 games) and Danny Santana (27 games) both saw some time there last year, but Gallo is better suited at a corner spot, and Santana did not grade out well with minus-3 defensive runs saved and a minus-29.8 UZR/150. There's still time to sign Kevin Pillar or swing a trade, but for now, it looks like the position will be up for grabs entering spring training.

NL East

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    Josh Donaldson
    Josh DonaldsonPatrick Semansky/Associated Press

    Atlanta Braves: Failing to Replace 3B Josh Donaldson

    The Braves took a chance on Josh Donaldson in 2019, and he rewarded them with a 127 OPS+ and 37 home runs in a 6.1-WAR season. Now he's a member of the Twins, and Atlanta has a glaring hole at the hot corner.

    The team signed Marcell Ozuna to replace some of his power production in the middle of the lineup, but it will now be counting on some combination of Johan Camargo and Austin Riley to handle third base. Not pivoting to a fallback plan like Todd Frazier or aggressively pursuing a trade for Kris Bryant or Nolan Arenado might be a decision the Braves regret.


    Miami Marlins: Not Adding a Veteran Innings-Eater

    Here's a look at the Marlins' projected rotation, along with their career-high innings total:

    • Caleb Smith (153.1 in 2019)
    • Sandy Alcantara (197.1 in 2019)
    • Jordan Yamamoto (144 in 2019)
    • Pablo Lopez (145.1 in 2017)
    • Elieser Hernandez (130.1 in 2019)

    Bridging the gap to rising prospects like Sixto Sanchez and Edward Cabrera with a low-cost veteran or two on a minor league deal would have been the ideal low-risk approach. If things went well, it also could have provided the rebuilding club with a trade chip or two when the deadline rolls around.


    New York Mets: Failing to Acquire CF Starling Marte

    Earlier this offseason, B/R's Zachary Rymer wrote that Starling Marte was the "must-have" prize of the offseason for the Mets.

    Instead, he wound up going to the Arizona Diamondbacks for a collection of low-level, high-ceiling prospects the Mets likely could have matched if they wanted to. That means they will move forward with an outfield of J.D. Davis, Brandon Nimmo and Michael Conforto, with Jake Marisnick and Dominic Smith also in the mix. Adding Marte to set the table at the top of the lineup would have given the offense another dimension.


    Philadelphia Phillies: Not finding a Platoon Partner for CF Adam Haseley

    Adam Haseley hit .282/.337/.441 with 12 doubles and five home runs in 185 plate appearances against right-handed pitching as a rookie last season. He batted a decidedly less impressive .212/.281/.250 with a 28.1 percent strikeout rate and just two extra-base hits in 57 plate appearances against lefties.

    Until Alec Bohm arrives in the majors and Scott Kingery can return to a super-utility role, oft-injured Roman Quinn looks like the closest thing the team has to a right-handed-hitting complement who can man center field. He hit .213 with a 72 OPS+ in 122 plate appearances last season.


    Washington Nationals: Leaving SP Sterling Sharp Unprotected in Rule 5 Draft

    Marlins president of baseball operations Michael Hill had this to say to reporters after the team selected Sterling Sharp from the Washington Nationals organization in the Rule 5 draft:

    "We got a lot of good feedback from him. This is not a high-velo guy. This is a different skill set and tool package than other guys in our pen. This is a guy who can put the ball on the ground, has a solid average to above-average change-up and can command his fastball. We've gone the route of the power arms and 100 mph fastballs that couldn't throw strikes. We're about trying to be efficient, pound the strike zone and get outs."

    The 24-year-old closed out a successful 2019 season with a stellar run in the Arizona Fall League, where he posted a 1.50 ERA and 0.92 WHIP with 24 strikeouts in 24 innings. The Nationals have a thin system, and the decision to leave him unprotected is one they could regret.

NL Central

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    Tyler Chatwood
    Tyler ChatwoodThearon W. Henderson/Getty Images

    Chicago Cubs: Relying on Tyler Chatwood to Fill a Rotation Spot

    In an offseason defined by stagnant inactivity, the Cubs' biggest regret could wind up being their failure to properly replace Cole Hamels in the starting rotation.

    Without any outside additions, it appears to be an open competition between failed starter-turned-solid reliever Tyler Chatwood and the relatively inexperienced Alec Mills. Guys like Adbert Alzolay, Colin Rea and Jharel Cotton could also be in the mix, but that group could have a tough time replacing Hamels.


    Cincinnati Reds: Not finding an Upgrade at Shortstop

    In a busy offseason that included the additions of Nicholas Castellanos, Mike Moustakas, Wade Miley and Shogo Akiyama, the Reds failed to find a suitable upgrade at shortstop.

    Cincinnati exercised Freddy Galvis' $5.5 million club option at the start of the offseason after it claimed him from the Blue Jays off waivers last August. Barring something unforeseen, he will break camp as the starting shortstop after posting 1.7 WAR last season. A run at bringing back Didi Gregorius would have been money well spent.


    Milwaukee Brewers: Overpaying for OF Avisail Garcia

    In a market where defensively superior players with similar offensive profiles in Kole Calhoun (two years, $16 million) and Corey Dickerson (two years, $17.5 million) also signed two-year deals, it looks like the Brewers overpaid for Avisail Garcia.

    Milwaukee signed him to a two-year, $20 million deal after he posted a 111 OPS+ with 20 home runs and 72 RBI for the Rays last year. However, his career minus-24 DRS in the outfield makes him better suited as an AL player who can be a part-time DH.


    Pittsburgh Pirates: Not Selling More Aggressively

    The Pirates landed a solid return for center fielder Starling Marte in a trade with the Diamondbacks, but that is the only piece they have sold in what was expected to be a busy offseason at the onset of a rebuild.

    Starter Chris Archer, reliever Keone Kela and perhaps even slugging first baseman Josh Bell are all potential trade chips with significant value. There's no reason for the new front office to drag its feet on rebuilding, as this looks like the clear-cut last-place team in the NL Central.


    St. Louis Cardinals: Not getting a Nolan Arenado Deal Done

    After losing Marcell Ozuna in free agency, the Cardinals could use another power bat in the middle of the lineup, and superstar third baseman Nolan Arenado has been a popular potential target on the rumor mill.

    According to Jon Paul Morosi of, the Rockies have shown interest in young starter Dakota Hudson and would likely ask for one of Dylan Carlson, Nolan Gorman, Matthew Liberatore or Andrew Knizner in a trade as well. It would be a bold move, but in an ultra-competitive NL Central, it could have been the trade that pushed the Cardinals over the top. There's still time to get a deal done.

NL West

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    Nolan Arenado
    Nolan ArenadoRick Scuteri/Associated Press

    Arizona Diamondbacks: Failing to Find a Trade Partner for SP Robbie Ray

    The Diamondbacks took a proactive approach to their top impending free agent last offseason, trading Paul Goldschmidt to the Cardinals for a pair of MLB-ready pieces in catcher Carson Kelly and starter Luke Weaver.

    A similar approach with free-agent-to-be Robbie Ray might have been in the team's best interest this offseason, especially after the dominoes at the top of the starting pitching market fell quicker than expected. Ray, 28, posted a 4.34 ERA with a career-high 235 strikeouts in 174.1 innings last season. He would likely have brought back at least a couple of quality prospects.


    Colorado Rockies: Failing to Find a Trade Partner for 3B Nolan Arenado

    The Rockies shopped superstar third baseman Nolan Arenado less than a year after he signed a massive extension, and he did not take kindly to being on the trade block.

    "There's a lot of disrespect from people there that I don't want to be a part of," Arenado told Thomas Harding of via text. "You can quote that."

    He later added: "I'm not mad at the trade rumors. There's more to it."

    An offseason of inactivity on the heels of a 91-loss season has made it clear the Rockies are content as also-rans. It could be a matter of time before Arenado demands a trade and robs them of significant leverage.


    Los Angeles Dodgers: Trading OF Alex Verdugo

    The Mookie Betts trade was the definition of an all-in move by the Dodgers. The longtime Red Sox star is headed for free agency after 2020, and the Dodgers front office under Andrew Friedman has shied away from significant free-agency splashes, so he is likely headed elsewhere next winter.

    In order to get the deal done, the Dodgers parted with rising star Alex Verdugo, who had five years of team control remaining after logging a 3.1-WAR season as a rookie. The 23-year-old has a chance to be a foundational piece, and if the Dodgers come up short in 2020, the decision to trade him will be an immediate regret.


    San Diego Padres: Not Upgrading the Starting Rotation

    The Padres added a solid veteran starter in Zach Davies on the trade market and have high hopes for a healthy season from Garrett Richards, but the starting rotation still lacks an established ace.

    Chris Paddack is capable of taking his game to another level, and top prospect MacKenzie Gore has No. 1 starter upside. But if the Padres want to take another step forward, finding the staff ace they've been pursuing for several years should have been a top priority.


    San Francisco Giants: Failing to Find a Trade Partner for SP Jeff Samardzija

    After a disastrous 2018 season, Jeff Samardzija rebounded last year to rank among the NL leaders in ERA (3.52, 14th), WHIP (1.11, 10th) and innings pitched (181.1, 15th).

    Entering the final year of his contract, Samardzija is still owed a hefty $19.8 million. However, if the Giants were willing to chip in enough money to cut that figure in half, they might have been able to add a couple more solid mid-level prospects to a farm system on the rise. The 35-year-old is not a long-term piece of the puzzle, and after he rebuilt value in 2019, this winter was the time to move him.


    All stats courtesy of Baseball Reference and FanGraphs unless otherwise noted.


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