5 MLB Offseason Decisions That Will Backfire Badly in 2019

Harry How/Getty Images

As the 2019 MLB season kicks off, let's polish our trusty B/R crystal ball and project five offseason decisions that will backfire badly for the franchises in question.

In some cases, it's a costly extension or contract option that shouldn't have been inked. In others, it's a trade that should have been consummated.

Or it might be a player who's getting paid richly—and unnecessarily—to play for someone else.

Across the board, it's about regret...at least in theory.

Jim Young/Associated Press

The Chicago Cubs opened their winter by exercising Cole Hamels' $20 million option. It seemed like a sign they were prepared to loosen the purse strings after losing to the Colorado Rockies in the National League Wild Card Game in 2018.

Since then, they have made no major moves despite playing in the toughest division in baseball.

Hamels pitched well for the Cubs after they acquired him from the Texas Rangers in a trade-deadline deal last season. At the same time, he's entering his age-35 campaign and hasn't posted a sub-4.49 FIP since 2016.

Spring stats don't matter, but it isn't great that he's surrendered 20 hits and 10 earned runs in 20 exhibition frames.

Having Hamels on the roster won't be detrimental for the Cubbies. But paying him $20 million when they apparently weren't willing or able to spend big to upgrade the lineup, bullpen or the remainder of the rotation is an odd look.

Michael Reaves/Getty Images

The Toronto Blue Jays are rebuilding. Veteran Troy Tulowitzki—and the $38 million they owed him through 2021—wasn't part of the plan.

So the Jays released Tulo, and he was picked up by the New York Yankees.

This spring, the 34-year-old has clubbed four home runs with eight RBI and posted a .970 OPS in 14 games for New York, which will pay him only the league minimum.

Perhaps he won't pan out in the Bronx. Undeniably, though, he has some gas sloshing in the tank.

Wouldn't the Jays have been better off letting him play out the spring and seeing whether they could find a trade partner willing to eat a portion of his salary and/or give back a prospect?

It doesn't look great to pay a guy millions of dollars to play for a divisional rival—let alone play well.

Jason O. Watson/Getty Images

The San Francisco Giants are in a state of flux under new president of baseball operations Farhan Zaidi. Maybe they're retooling. Maybe they're rebuilding. Maybe they're going for it.

They appear to be taking the latter approach. They didn't sign any marquee free agents, but they've added ancillary pieces around their aging core.

Zaidi's hand was forced, to some extent, by the Giants' lack of bankable trade assets. One exception? Ace left-hander Madison Bumgarner.

MadBum is entering a contract year and is signed for an affordable $12.5 million. Even after a down season marred by injury (most notably a fractured pinkie suffered in spring training 2018), Bumgarner is correctly regarded as a postseason legend.

The Giants kept him this winter, however. The idea, seemingly, is to wait until July and then flip him at the non-waiver trade deadline if needed.

That will be fine if San Francisco contends or if Bumgarner performs up to snuff. The first proposition is unlikely. As for the second?

Spring stats aren't predictive, but Bumgarner posted an 8.27 ERA in the Cactus League. If he falters in the regular season and the Giants slip in the standings, they will wish they had traded him when his value was higher.

Gerald Herbert/Associated Press

Extensions are all the rage in MLB, hence the five-year, $145 million pact Chris Sale signed with the Boston Red Sox before he was set to hit free agency after the 2019 season.

Sale has made seven straight All-Star teams and finished no worse than sixth in Cy Young Award balloting in that span. He's 29 and posted a 2.11 ERA with 13.5 strikeouts per nine innings in 2018. 

On the other hand, he battled shoulder issues in 2018, and this extension will carry him into his mid-30s.

As an unnamed official asked, per ESPN.com's Buster Olney: "If you're going to pay him like an elite free agent, why not wait until the year's out so you can gather some more information about where he is physically?"

It's a great question. Sale has been excellent with the Sox. They hoisted the Commissioner's Trophy together.

On the other hand, this seems like Boston bidding against itself and dishing out dollars it didn't need to, especially with the specter of superstar outfielder Mookie Betts' post-2020 free agency hanging in the air.

Matt Slocum/Associated Press

Clayton Kershaw is the greatest pitcher of his generation. He's won three National League Cy Young Awards and snagged an NL MVP in 2014.

This winter, The Los Angeles Dodgers extended Kershaw for three years and $93 million, ensuring he will be a Dodger through 2021.

Now, the left-hander is hurting. Specifically, his left shoulder.

On March 20, Kershaw estimated a timetable of 20 days for his debut, per MLB.com's Ken Gurnick. If that sounds like a shot in the dark, that's probably because it is.

Kershaw is 31. He's not thrown a spring inning. His shoulder is barking, and his debut is nebulous. None of this is good news for the Dodgers as they try to get over the hump after two consecutive World Series losses.

They basically had to extend Kershaw from a PR point of view. From a baseball point of view, maybe they shouldn't have.

All statistics courtesy of Baseball Reference and FanGraphs.