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Ranking MLB's Most Crushing 2019 Offseason Regrets

Jacob ShaferMar 4, 2019

Spring training is underway, but the MLB offseason isn't technically over. As of this writing, multiple marquee free agents remain unsigned, including studs such as ace left-hander Dallas Keuchel and decorated closer Craig Kimbrel.

As we enjoy actual baseball action and hum toward Opening Day, it's worth examining and ranking six of the winter's most crushing regrets.

There's a healthy degree of subjectivity and guesswork involved, obviously. We judged teams most harshly for moves they didn't make and based our rankings on how badly a club needed to make said move to improve.

Overall, we sifted through the worst contracts, missed opportunities and fizzled trades to bring you a half-dozen deals that should or should not have gone down.

No. 6: Texas Rangers Giving Lance Lynn 3 Years and $30 Million

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On Dec. 12, the Texas Rangers reached an agreement with right-hander Lance Lynn on a three-year, $30 million contract. That's not egregious by today's standards, but it's a hefty commitment.

Now let's add the fact that Lynn posted a 4.77 ERA in 2018 between the Minnesota Twins and New York Yankees and turns 32 in May.

Yes, the 3.84 FIP he put together last season suggests a degree of bad luck. But the Rangers should be looking to rebuild, not lock up relatively costly veterans into their mid-30s. 

Given the way the pitching market has unfolded (again, Keuchel remains unsigned), Lynn's pact is a significant overpay for a club that ought to be going in the opposite direction. 

No. 5: San Francisco Giants Not Trading Madison Bumgarner

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The San Francisco Giants and new president of baseball operations Farhan Zaidi are in a tricky position. They're loaded with expensive contracts and playing out the fading days of their even-year dynasty, caught between a retool and a rebuild.

The obvious play this winter seemed to be trading left-hander and postseason legend Madison Bumgarner. 

The 29-year-old is signed for an eminently affordable $12 million in 2019. After that, he'll enter free agency.

Given his October pedigree, it seemed almost certain some title-starved contender would open the prospect vault for a year of his services. 

Instead, barring a last-minute trade, Zaidi and the Giants will likely keep Bumgarner at least until the July 31 non-waiver deadline. 

Maybe San Francisco will turn back the clock and contend. Perhaps MadBum will fetch a rich return this summer. Then again, the Giants might have held on to their best trade asset too long.

No. 4: Boston Red Sox (So Far) Not Acquiring a Closer

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The Boston Red Sox need help at the back end of the bullpen. Craig Kimbrel, who has been an All-Star in each of his three seasons with the Sox, is a free agent. 

Boston could lean on in-house options such as right-handers Matt Barnes and Ryan Brasier, but neither has the track record to anchor the defending champions' relief corps.

The Washington Nationals are in hot pursuit of Kimbrel, per ESPN.com's Keith Law. Other clubs could jump in. Fallback options such as Adam Ottavino, David Robertson and Zach Duke have fallen off the board.

Maybe the Red Sox and Kimbrel will reunite at the eleventh hour. Or maybe Boston will embark on its title defense with a closer-sized question mark.

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No. 3: Cleveland Indians Not Doing Enough to Address the Outfield

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The Cleveland Indians outfield features an array of contenders but few if any safe bets after bidding adieu to free agents Michael Brantley, Melky Cabrera, Rajai Davis, Lonnie Chisenhall and Brandon Guyer. 

At the moment, Tyler Naquin, Jake Bauers, Leonys Martin, Greg Allen, Jordan Luplow, Brandon Barnes, Matt Joyce and Trayce Thompson top the Tribe's depth chart.

That might be enough for Cleveland to reign supreme in a weak, winnable American League Central. Then again, the Minnesota Twins bettered themselves this winter, and the youthful Chicago White Sox are on the rise. 

Even if the Indians stave off their division foes, they'll be hard-pressed to hang with the AL's elite (the Yankees, Red Sox and Houston Astros) without adding muscle to a muddled outfield. 

No. 2: New York Yankees Not Signing Bryce Harper

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The Yankees boast adequate outfield depth with Aaron Judge, Aaron Hicks, Brett Gardner, Clint Frazier and veteran Jacoby Ellsbury (provided he's healthy), among others. 

Yet, the Yankees could have used a left-handed bat to balance their righty-heavy lineup. 

Cough, Bryce Harper.

Instead, New York stayed on the sidelines while other teams courted the 26-year-old superstar, who eventually signed a record-breaking 13-year, $330 million deal with the Philadelphia Phillies. 

Will Harper's pact sting on the back end as he lurches into his late 30s? Of course.

Are the Yankees a World Series contender without him? Yes.

Does it make sense that the Bronx Bombers, MLB's perennial big spenders, were hardly involved in negotiations for one of this generation's glitziest superstars? Nope.

Imagine Harper joining Judge, Giancarlo Stanton et al. at hitter-happy Yankee Stadium in the game's biggest market. It simply makes too much sense, future cash considerations be damned. Once upon a time, that was the Yankee way.

Now, apparently, not so much.

No. 1: Chicago Cubs Giving Cole Hamels $20M...and That's It?

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The Chicago Cubs opened the offseason by exercising Cole Hamels' $20 million option. Hamels pitched well after coming over from the Texas Rangers in the deadline trade last season, posting a 2.36 ERA in 76.1 innings for the Cubbies. 

He also turned 35 in December and posted a 4.49 FIP overall. 

He could be a solid arm for Chicago in 2018, but the Cubbies did little else after handing Hamels his cash. Further seismic upgrades to the rotation, bullpen and lineup weren't forthcoming. What happened to Harper?

The Cubs will amble into 2019 in a deep division with a roster PECOTA projects for a last-place 79-83 finish. 

They could exceed expectations. But after tossing undue cash at Hamels and essentially calling it a winter, executive Theo Epstein and company have left themselves open to justifiable criticism. 

All statistics and contract information courtesy of Baseball Reference unless otherwise noted.

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