White Sox: Three biggest missed opportunities

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.

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.

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.

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