White Sox: Three biggest missed opportunities

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.

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.