White Sox: Three biggest missed opportunities

NEW YORK, NEW YORK - SEPTEMBER 26: Zack Wheeler #45 of the New York Mets follows through with a pitch in the first inning of their game against the Miami Marlins at Citi Field on September 26, 2019 in the Flushing neighborhood of the Queens borough in New York City. (Photo by Emilee Chinn/Getty Images)
NEW YORK, NEW YORK - SEPTEMBER 26: Zack Wheeler #45 of the New York Mets follows through with a pitch in the first inning of their game against the Miami Marlins at Citi Field on September 26, 2019 in the Flushing neighborhood of the Queens borough in New York City. (Photo by Emilee Chinn/Getty Images)
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The Chicago White Sox had a very productive offseason and there’s no question about that. But, could it have been better than it ended up being? 

Personally, I believe the answer is yes. I will also acknowledge, though, that the same could be said about pretty much every franchise.

There’s not a team in baseball that absolutely accomplished everything they should have this offseason, except for maybe the New York Yankees whose only goal was to make sure Gerrit Cole was wearing pinstripes in 2020.

Even they, though, missed out on some opportunities to improve their roster further despite achieving their goal.

The White Sox are no exception to this rule and I think that there are certainly some areas that could have been improved better.

One position that could not have been improved was the catcher spot where Yasmani Grandal was without question the perfect acquisition for the team as exemplified by his number one ranking among catchers in the game right now by MLB Network.

There’s a lot to be excited about on the South Side in 2020, but it could have even been better if any of these three potential signings came to fruition.

NEW YORK, NEW YORK – SEPTEMBER 10: Zack Wheeler #45 of the New York Mets pitches in the first inning against the Arizona Diamondbacks at Citi Field on September 10, 2019 in New York City. (Photo by Mike Stobe/Getty Images)
NEW YORK, NEW YORK – SEPTEMBER 10: Zack Wheeler #45 of the New York Mets pitches in the first inning against the Arizona Diamondbacks at Citi Field on September 10, 2019 in New York City. (Photo by Mike Stobe/Getty Images) /

1. Zack Wheeler

The Chicago White Sox appeared to make the right-hander their top target from the get-go when it came to signing starting rotation help.

At one point, it appeared that the White Sox were the frontrunners for him and it was later revealed that they made the highest bid to sign him.

However, he chose to sign a five-year, $118 million contract with the Philadelphia Phillies instead which left the White Sox scrambling to their fallback options.

Had the team signed Wheeler, he probably would’ve slotted in right behind Lucas Giolito in the rotation. That’s a spot in the rotation that Dallas Keuchel, at least as of right now, will call his home in 2020.

Wheeler, 29, was coming off a season with the Mets in which he had a 3.96 ERA, 3.48 FIP, 8.98 K/9, and 2.30 BB/9. His walk rate and fWAR (4.7) were the best of his career so far.

Long term, Wheeler seems like a good bet to continue improving and the fact that he threw 195 1/3 innings in 2019 suggests that his health issues of the past are behind him now.

Having an arm with the potential to breakout like Wheeler would have been really nice behind Giolito.

HOUSTON, TEXAS – OCTOBER 29: Stephen Strasburg #37 of the Washington Nationals delivers the pitch against the Houston Astros during the ninth inning in Game Six of the 2019 World Series at Minute Maid Park on October 29, 2019 in Houston, Texas. (Photo by Bob Levey/Getty Images)
HOUSTON, TEXAS – OCTOBER 29: Stephen Strasburg #37 of the Washington Nationals delivers the pitch against the Houston Astros during the ninth inning in Game Six of the 2019 World Series at Minute Maid Park on October 29, 2019 in Houston, Texas. (Photo by Bob Levey/Getty Images) /

2. Stephen Strasburg

The White Sox actually might’ve pivoted to this right-hander after Wheeler signed with the Phillies as Jon Morosi of MLB.com reported that they were a “dark horse” to sign Strasburg.

Whether or not they actually did make an offer for him is unknown, but it certainly was a missed opportunity.

In fact, it could be argued that it was a bigger one than Wheeler as Strasburg is an established ace coming off a year in which he won World Series MVP for the Nationals.

The 31-year-old registered a 3.32 ERA, 3.25 FIP, 10.81 K/9, and 2.41 BB/9 in 2019. He also had a 5.7 fWAR, which was the second-highest mark of his career and his 209 innings of work were the highest he had thrown since 2014 (215 innings).

Strasburg’s age coupled with the seven-year, $245 million contract it took the Nationals to keep him might have made the White Sox balk at signing him.

Had the White Sox signed him, though, the team would have had instant credibility with a one-two punch at the top of the rotation that would’ve been second to none.

Their reluctance to sign Strasburg is very understandable, but it would have put made a statement to the American League if they got him.

CHICAGO, ILLINOIS – SEPTEMBER 16: Nicholas Castellanos #6 of the Chicago Cubs hits a two run double in the eight inning against the Cincinnati Reds at Wrigley Field on September 16, 2019 in Chicago, Illinois. (Photo by Quinn Harris/Getty Images)
CHICAGO, ILLINOIS – SEPTEMBER 16: Nicholas Castellanos #6 of the Chicago Cubs hits a two run double in the eight inning against the Cincinnati Reds at Wrigley Field on September 16, 2019 in Chicago, Illinois. (Photo by Quinn Harris/Getty Images) /

3. Nicholas Castellanos

Of the three possible additions, this was the one that would have cost the least to make happen as Castellanos only required a four-year, $64 million contract from the Cincinnati Reds.

However, this was probably the most questionable of their decisions to make as, instead of signing Castellanos, the team decided to trade for Nomar Mazara.

While it’s certainly possible that trade could work out, Mazara doesn’t exactly have a track record of success in the big leagues, He hasn’t even had a season where he had a 1.0 fWAR yet.

Castellanos, 27, would have been a major addition to the lineup in 2020 after hitting .289/.337/.525 with 27 home runs and 73 RBI to give himself a 121 wRC+ and 2.8 fWAR this past season.

His fWAR was lower due to the fact that his defense has not been good over the course of his career.

With that being said, he did show some improvement in 2019 with -9 DRS as compared to -19 in 2018 while also improving his UZR to -4.4 as compared to his abysmal -12.9 UZR in the year prior.

Even if the team determined that he wasn’t capable of playing right field every day, they could have signed him for their DH spot. However, they instead chose to sign Edwin Encarnacion.

Mazara and Encarnacion could certainly work out for the team in 2020, but I also believe that Castellanos would have been a big-time addition for the team.

The good news is that they might get another crack at Castellanos next offseason as his contract contains an opt-out after the 2020 season as detailed by Jeff Passan of ESPN.

Next. White Sox's Three Best Offseason Moves. dark

That allows the White Sox to evaluate Mazara and, if he doesn’t succeed, they can simply do a course correction after this season.

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