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Fair or Foul: Each 2020 AL playoff team’s last big free agent signing… and how they turned out

While every baseball fan awaits the big news that their favorite team has reached a deal with a marquee free agent, the last move of that caliber made by these clubs cannot be forgotten.

For some teams, that massive eight-figure deal handed out to a superstar player comes once every few seasons. For others, such a deal comes once a decade, and some simply do not possess the means to make deals like that at all. 

With that in mind, here is each 2020 American League playoff team’s last big multi-year free-agent signing, as well as what transpired during that player’s tenure.

Toronto Blue Jays: Hyun-Jin Ryu (four years, $80 million, 2019 offseason)

One of the more recent transactions, Ryu had an unbelievable first half of 2019 with the Los Angeles Dodgers, and gave himself a real shot at a Cy Young Award. He stayed healthy and pitched better than ever, but the Dodgers let him go and the Blue Jays handed him a hefty paycheck to captain their pitching staff. 

In his first year north of the border, he may have averaged only about 6 innings per start, but he had a 2.69 earned run average and was the only consistently strong arm in that rotation. He may not be super young, but a healthy Ryu is a gem for this budding Blue Jays team.

Chicago White Sox: Yasmani Grandal (four years, $73 million, 2019 offseason)

Grandal infamously inked a one-year deal with the Milwaukee Brewers before the 2019 season after turning down longer-term deals. None of them gave him the annual value he wanted. His 2019 campaign earned him the payout he desired from the South Siders. As a veteran catcher who can block well, frame pitches brilliantly and keep the young pitching core in check, Grandal was exactly what the White Sox needed. 

Although his regular season in Chicago was average, his postseason was great. And he brings much more than statistics to that club.

Minnesota Twins: Ervin Santana (four years, $54 million, 2014 offseason)

This deal is the furthest back in time on this list so far. While Nelson Cruz is also a valid option here, I focused on multi-year deals. The then-32-year-old Santana was returning to the AL after a year with the Atlanta Braves, and a bumpy start led to two strong campaigns in 2016 and 2017. 

In those two years, he averaged a 3.33 ERA while also posting 392.2 innings pitched in 63 total starts. Although his career crashed shortly after the 2017 Wild Card game, Santana still had a solid tenure in Minnesota.

Tampa Bay Rays: Charlie Morton (two years, $30 million, 2018 offseason)

The Rays are famous for their low payroll. As such, if they intend to spend money, it cannot be an enormous pile of it. And they need to spend it on the right guy. 

Two years ago, they did just that when they landed Morton. The then-35-year-old provided an innings-eating veteran presence in a rotation with young, talented arms like Tyler Glasnow and Blake Snell. He ended up finishing third in the 2019 AL Cy Young Award voting as the Rays made the playoffs. Morton pitched for them again during their 2020 World Series run.

Cleveland Indians: Edwin Encarnación (three years, $60 million, 2016 offseason)

Encarnación came to Cleveland fresh off a five-season run in Toronto from 2012 to 2016, during which he averaged a 0.912 on-base-plus slugging percentage and hit a total of 193 home runs. 

He more than earned his paycheck with the Indians, as he provided some right-handed power to a lineup that already featured Michael Brantley and the up-and-coming duo of Francisco Lindor and José Ramírez. 

He clubbed 70 homers in his first two seasons in Cleveland before getting traded to Seattle and then to the New York Yankees. Cleveland did not win a title with him, but his productivity remained.

Houston Astros: Michael Brantley (two years, $32 million, 2018 offseason)

Brantley continues to thrive in the majors due to his ability to hit for contact and keep the strikeouts to a minimum. Such a skill set was much needed on an Astros team that had many well-developed, but sometimes swing-happy, hitters such as José Altuve, George Springer, Yuli Gurriel and Alex Bregman. 

After batting 0.309 with just 94 total strikeouts in 745 at bats between 2019 and 2020, Brantley could be eyeing a new multi-year deal on the market heading into 2021.

Oakland Athletics: Yoenis Cespedes (four years, $36 million, 2012 offseason)

The champion of early deals on this list, Cespedes did indeed come to the majors with the Athletics, and 2022 marks a decade since he received his first MLB contract. Cespedes was inconsistent during his roughly two-and-a-half seasons in Oakland, batting as high as 0.292 and as low as 0.240, all while flexing his unreal arm and striking out a lot. 

His character issues got him traded twice in less than a year before he landed with the Mets, where the tumult has amplified exponentially. His A’s career is forgotten by some, but this was the last time the A’s dished out money like this to any player — and it was not at all worth it.

New York Yankees: Gerrit Cole (nine years, $324 million, 2019 offseason)

Lastly comes one of the several nine-figure deals during general manager Brian Cashman’s tenure. 

Cole came in with a very clear purpose of becoming the ace the Yankees went the last two years without. New York knew they needed a big-time hurler before the 2020 season, and Cole seemed like a much more feasible target, with Stephen Strasburg likely to remain with the Washington Nationals. 

While his first regular season in the Bronx was both inconsistent and truncated, he carried the rotation in the playoffs, and will hopefully continue to do so in the years to come.

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