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What do biggest playoff moments mean for White Sox as they build for future Octobers?

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USA TODAY

What do biggest playoff moments mean for White Sox as they build for future Octobers?

That was just the first round?

This year’s edition of playoff baseball has been wildly entertaining, and there are two more rounds to play. That should be wonderful news for every baseball fan out there, but obviously the viewing pleasure of folks on the South Side would be cranked to 11 if their team was present.

The White Sox are trying to do just that through their ongoing rebuilding project, and the end of their 11-year postseason drought could come as soon as next season — at least that’s the hope of manager Rick Renteria and his players, who weren’t shy about voicing their 2020 expectations at the end of the 2019 season.

It’s expected to be a busy winter for Rick Hahn’s front office, but until that winter rolls around and that 2020 roster starts taking shape, the South Side will have to settle for this riveting postseason for their baseball-related entertainment. Though the White Sox aren’t playing, that doesn’t mean what’s going on on the game’s biggest stage doesn’t apply to their quest for perennial contention. Let’s discuss.

Gerrit Cole is going to be worth every penny

The biggest name on this winter’s free-agent market will be Gerrit Cole, who is making himself richer by the inning. Cole was unbelievable in his two starts against the Tampa Bay Rays in the ALDS, pitching his Houston Astros into the ALCS with his work in Game 5 on Thursday night.

In his first two outings this postseason, Cole allowed one run and struck out 25 in 15.2 innings. His 15 punchouts in Game 2 against the Rays were the third most in a playoff game in baseball history. As if Cole’s AL-leading 2.50 ERA and baseball-leading 326 strikeouts during the regular season — which could win him a Cy Young — weren’t enticing enough to prospective employers, his October efforts have dropped jaws on the game’s biggest stage.

The White Sox will undoubtedly be in the market for starting-pitching improvements this winter, and there will be many intriguing names out there. But none will be bigger — or more expensive — than Cole. There’s a ton of reasons the 29-year-old should be at the top of any team’s wish list. The price tag, however, might keep some teams away. Will the White Sox be one of them?

They showed no hesitation in jumping into the derbies for the two most expensive players on last offseason’s free-agent market, Bryce Harper and Manny Machado, but wound up outbid, reportedly $50 million shy, in terms of guaranteed money, of the $300 million Machado got from the San Diego Padres.

Rick Hahn has been adamant about several things of note here. First, he has promised that the team’s financial flexibility will be utilized to bring in impact players, saying in wake of Machado picking the Padres that “the money will be spent. It might not be spent this offseason, but it will be spent at some point. This isn’t money sitting around waiting to just accumulate interest. It’s money trying to be deployed to put us in best position to win some championships.” Hahn has also vowed to disprove what he refers to as “false narratives” about the franchise, one that the White Sox won’t spend the money necessary to land a big free agent or that they won’t spend it on a long-term deal for a pitcher.

Well, Cole would certainly provide an opportunity to do those things. But it will take an awful lot of dough, the amount of which seems to only be growing as Cole continues to mow down every lineup he sees. The guy hasn’t lost a game since May 22, when he, coincidentally, lost to the White Sox. Since then, he’s 18-0 with a 1.66 ERA and the Astros have a 22-2 record in games he pitches.

Basically, Cole looks to be worth every penny of the monstrous, perhaps record-breaking contract he’s going to receive, and the attraction goes without saying. Putting Cole at the top of the South Side rotation alongside Lucas Giolito and Michael Kopech for the next however many years would be a dream for Hahn’s front office, not to mention White Sox fans.

But there will be other teams trying to do the same thing. The White Sox might be in a good position, financially, but Hahn thinks there’s a bigger attraction for free agents.

“The biggest advantage we have is the talent base we've accumulated so far and the excitement to come and be part of that,” he said during his end-of-season press conference last month. “We do have some economic flexibility. That was part of the plan from the start. But I think if you're looking at advantages, a lot of teams have money. A lot of teams don't offer the ability to play with some of the players that are joining us here already and joining in the coming years and the opportunity to win a championship in a city like Chicago.”

We’ll see if that all mixes together to lure Cole to the South Side, away from the potential draw of playing in his native Southern California. For what it's worth, he went to high school a 10-minute drive from Angel Stadium.

Juan Soto is a star, is Luis Robert next?

The Washington Nationals got the monkey off their back in thrilling fashion, winning their first-ever postseason series by knocking off the 106-win Los Angeles Dodgers in the NLDS. Surely you saw how they did it, with Clayton Kershaw coughing up a two-run lead on back-to-back homers off the bats of Anthony Rendon and Juan Soto in the eight inning of Game 5. Howie Kendrick won the game and sent the Nats to the NLCS with a 10th-inning grand slam, but let’s keep the focus on the 20-year-old Soto, who’s delivered a few supremely clutch moments in the first six playoff games of his career.

Soto was a commonly used as a reference point when White Sox fans were clamoring for the midseason promotion of Luis Robert, the top-ranked prospect in the organization. That promotion never came, obviously, and unless the team can work out a contract similar to the one they signed Eloy Jimenez to last spring, Robert’s debut will most likely be delayed until the middle of April.

Plenty of fans wished the White Sox would have done what the Nationals did with Soto, who played all of eight games above A-ball — and skipped Triple-A altogether — before getting his big league call last year. Robert put on a show at three different levels this season, showing, at least from a results standpoint, a pretty convincing mastery of each one. Could the then 21-year-old Robert have come up and mashed at the major league level like Soto did as a 19-year-old in 2018?

Soto hit the ground running, with a second-place finish in Rookie of the Year voting last year followed by a 34-homer, 110-RBI campaign this year prior to a pair of instantly iconic postseason moments: his bases-clearing single off Josh Hader to win the NL wild card game and the ridiculous 449-foot bomb he blasted off Kershaw to tie Wednesday’s game.

Soto’s a star. And White Sox fans think Robert will be, too. Plenty of them think he would’ve been one already had the team promoted him this season, while he was in the middle of a sensational campaign that ended with him as the minor league player of the year. Those with that opinion point to Soto and ask, “Why wait?”

Obviously we don’t know whether Robert would have done the same had he skipped a level or two and sprinted straight to the majors. We won’t find out until next season what he’ll do in his first taste of major league pitching.

But we do know that the White Sox and the Nationals are in two very different spots as franchises. The Nationals brought Soto up to aid in their (eventually unsuccessful) quest to make the playoffs last season. He’s helped them get four wins away from the World Series this year. The White Sox, as their 89 losses well illustrated, were not in a position where the in-season promotion of Robert would have drastically improved their chances of making the postseason. Certainly it wasn’t worth forfeiting team control down the line, when the White Sox do hope to be in a position to win the World Series.

But the Nationals' decision has certainly paid off with Soto. Maybe Robert will arrive as the next young, instant-impact bat in the big leagues.

More free agents to-be

Cole isn’t the only postseason star that could be in the White Sox sights this winter.

The aforementioned Rendon has been excellent, with seven hits in the postseason so far, three of them doubles and one the clutch homer off Kershaw. He owns a 1.073 OPS thanks to four walks to go along with those extra-base knocks. That goes along with the kind of MVP-level production Rendon puts up on an annual basis. This season’s damage amounted to a career-best 1.010 OPS, a career-best 34 homers, a career-best 126 RBIs, a career-best 44 doubles, et cetera, et cetera. He plays third base, which doesn’t exactly square with the White Sox positional needs, but that bat is too big to ignore.

Rendon’s Nationals teammate Stephen Strasburg can opt out of his deal and hit the free-agent market, where he’d figure to do quite well considering the kind of dominant outings he can turn in. After three innings of scoreless relief in the NL wild card game, he allowed four runs in 12 innings, striking out 17 Dodgers in two NLDS starts. He’s showed on this big stage why he could be the kind of rotation-topping addition a pitching-hungry team like the White Sox craves.

After leading the National League with a 2.32 ERA, Hyun-Jin Ryu didn’t get as much opportunity as everyone thought he was going to get to show off in October once his Dodgers were upset in five games and prevented from a third straight pennant. But he did his job in his lone outing, limiting the Nationals to two runs in five innings in a game his team won. Considering how much money the guys at the top of the starting-pitching market are expected to get this winter, Ryu could be a more affordable add, which is kind of nuts considering he’s going to finish pretty high in Cy Young voting.

Dallas Keuchel was not quite as good for the Atlanta Braves, who suffered their own unexpectedly early exit in their NLDS matchup with the St. Louis Cardinals. After doing a fine job as a midseason pickup for the Braves, he started twice in the NLDS and was tagged by the Cardinals for four runs in his eight innings. He was good in Game 1 but left before the end of the fifth inning. He gave up three homers in his Game 3 start and didn’t get out of the fourth. It shouldn’t do too much to limit his attractiveness to a team like the White Sox, whose rotation could certainly use a reliable, veteran pitcher who has a Cy Young Award on his resume and a World Series ring on his finger.

Accounting for two of the three homers off Keuchel in Game 3 of that NLDS was Marcell Ozuna, the corner outfielder who will hit free agency after his Cardinals wrap their postseason run. He had a less-than-stellar season by his standards, finishing with a career-worst .243 batting average and numbers far from the ones he put up in his spectacular 2017 season. But he’s made some noise in October, those two dingers part of a .429/.478/.857 slash line he has through his first five games, all but one of which have featured multiple hits. Ozuna is a left fielder, and the White Sox need a right fielder. He’s also a right-handed hitter, when their quest for a right fielder might be their best shot to add a left-handed bat to the lineup. Still, Ozuna is just 28 years old and is showing what kind of offensive force he can be.

Starters are starring, but you need a ‘pen

The White Sox are in the market for pitching for a reason, and the starting rotation had plenty of issues in 2019. But the South Side bullpen was actually quite good, finishing with a 4.33 ERA that ranked only behind the five playoff teams and the Cleveland Indians in the American League. Going into 2020, the relief corps figures to be a bit of a strength after the strong 2019 campaigns from Alex Colome, Aaron Bummer, Evan Marshall and Jimmy Cordero.

Renteria doesn’t need to be thinking about how he’d deploy his relievers in a playoff series quite yet, but watching this postseason, the constant use of starting pitchers out of the bullpen shows how valuable a reliable bullpen can be.

The Nationals are into the NLCS because of it, with Strasburg, Max Scherzer and Patrick Corbin used as much as the team’s relievers by Dave Martinez. They’ve been mostly effective, too. Strasburg pitched three scoreless innings in relief in the NL wild card game. Scherzer faced three batters and struck them all out in the eighth inning of Game 2 of that series with the Dodgers. Corbin was crushed in Game 3 when he entered in the sixth but then struck out three of the five hitters he faced in relief in the series-deciding Game 5 on Wednesday night.

Those relief appearances have made for some pretty fun playoff moments, but they also reveal that the Nationals don’t have much of a bullpen. Their relief ERA was an abysmal 5.68 this season, the worst in the National League and second worst in the majors, ahead of only the Baltimore Orioles. Outside of Sean Doolittle and former White Sox pitcher Daniel Hudson, Martinez doesn’t seem to have anyone he can rely on down there, hence the constant use of his starters. While the Nationals have made it to baseball's final four, you certainly wonder how long they can keep going, especially now that the series morph to best-of-seven affairs, riding those three pitchers over and over again.

Dave Roberts fell into the same trap in Game 5 of that series, with Kershaw infamously facing three hitters and blowing the game by giving up homers to two of them. Roberts’ situation was a bit different, as the Dodgers had an excellent bullpen all season and just didn’t use it when he probably should have. But it was the difference in the series. Julio Teheran, a starter, gave up the walk-off winner to the Cardinals in Game 4 of their series with the Cardinals. Even the mighty Astros were bitten by the starting-pitcher-pitching-in-relief-bug when Wade Miley gave up a pair of earned runs in Game 3 against the Rays.

The Cardinals experienced a couple bullpen disasters in their series with the Braves, with closer Carlos Martinez giving up six runs and two homers — not to mention three walks — over his three outings, blowing the save in Game 3. They won the series, though, in part by getting to Braves import closer Shane Greene, who blew the save in Game 4.

So for as sterling as the starting pitching has been from the likes of Cole, Strasburg, Scherzer, Walker Buehler, Justin Verlander, Ryan Flaherty and Charlie Morton in these playoffs, the need for a good bullpen — an elite bullpen — has loomed large, too. The White Sox have a good one, which is a good start.

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Jed Hoyer on not trading for Justin Verlander: 'Of course we have regret.'

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USA Today

Jed Hoyer on not trading for Justin Verlander: 'Of course we have regret.'

Cubs GM Jed Hoyer was asked on 670 The Score if he had regrets over trading for José Quintana instead of Justin Verlander.

“Of course we have regret.”

In case you’ve somehow forgotten, the Cubs were one of Justin Verlander’s preferred teams before the trade deadline in August of 2017. The Cubs and the Detroit Tigers couldn’t reach a deal, but the Cubs had already traded for Quintana and were comfortable with where they stood. 

After the trade fell through, Verlander didn’t go away quietly, but instead reinvigorated his career on the Astros. The Astros traded three prospects—Franklin Perez, Daz Cameron, and Jake Rogers— in exchange for Verlander and boy did that pay off. Verlander went on the win the World Series with the Astros in 2017. With this most recent no-hitter, Verlander is a real contender to win his second Cy Young Award. Following this past Sunday's outing, he has a 2.43 ERA in 68 starts with Houston. And this doesn’t even include his nine postseason appearances since the trade.

Hoyer went on to say, “There's ones that you beat yourself up over because you think, 'What could we have seen differently? Could we have predicted this?' Obviously, we didn't. His late-career resurgence has been amazing.”

It’s hard to imagine what recent seasons would’ve looked like if Verlander made it to Wrigley like he had once hoped. Quintana was a promising veteran starter for the Sox, but following the trade his ERA has hovered around to 4.00 during his tenure with the Cubs. Overall Quintana has been a decent player with the Cubs, but what’s done is done, and it is an interesting (and mildly infuriating) to wonder “what if.”

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The end goal of the White Sox rebuild? Be like the Astros

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USA TODAY

The end goal of the White Sox rebuild? Be like the Astros

The White Sox are walking down the same path as the Houston Astros. Of course, whether they arrive at the same destination remains to be seen.

The Astros went through the same loss-heavy, developmental seasons the White Sox have experienced for the last three years. But their mostly homegrown rebuilding strategy paid off in the form of a World Series championship in 2017, and they remain one of the favorites to win the whole thing this season, too.

That’s what the White Sox are trying to do, obviously.

“They’re certainly one of the best examples of someone who has done it well,” manager Rick Renteria said before Tuesday’s doubleheader against the visiting Astros. “On the North Side, they’ve done a nice job of doing the same thing. I think Cleveland kind of did a little of the same thing a few years back, and they still have the remnants of those guys on that ballclub. And I hope that we are one of those guys that end up doing the same things.”

Impatient White Sox fans sick of the losses that have piled up at the major league level in recent seasons — 95 of them in 2017, 100 more last season and 64 during the team’s first 116 games this year — can look at the same thing happening, to a much greater degree, in Houston several years back. The Astros lost a combined 416 games in four seasons from 2011 to 2014.

Three years after the last of those, a 92-loss campaign in 2014, the Astros were world champs, thanks in large part to a homegrown core of superstars like Jose Altuve, George Springer, Carlos Correa and Alex Bregman.

Well, the White Sox are in the process of building their own homegrown core, with several of those players already on the South Side. Tim Anderson and Yoan Moncada are in the midst of breakout seasons, with Eloy Jimenez creating plenty of highlights during his rookie season. Luis Robert and Nick Madrigal figure to join that group relatively soon, too.

The White Sox also potentially have something brewing the Astros (and the Cubs and Kansas City Royals before them, for that matter) never managed to accomplish: a mostly homegrown starting rotation. Lucas Giolito was an All Star this season, Reynaldo Lopez is pitching tremendously since the All-Star break, Dylan Cease is here, and Michael Kopech will return to the starting staff in 2020. If you want to include other names like Carlos Rodon, Dane Dunning and Jimmy Lambert in that group, too, go right ahead.

There’s a lot that needs to happen before they do what Giolito said they have the potential to do and become “one of the most dominant rotations in baseball.” But if even three of that group of young arms become good major league starting pitchers, that will be an accomplishment not experienced by the Astros, Cubs or Royals during those teams’ rebuilding projects.

Of course, even if it does happen, it’s not going to stop Rick Hahn’s front office from doing something those three teams did with great success: add high-impact starting pitching from outside the organization. The Astros traded for Justin Verlander, Gerrit Cole and Zack Greinke, so they are the best example, but the Cubs’ franchise-altering signing of Jon Lester and the Royals’ midseason deal for Johnny Cueto led to World Series wins, too.

Hahn has clearly stated that going out and getting some starting pitching will be an offseason priority for the White Sox this winter — maybe a run at Cole? — and so there’s another page he hopes to take from the Astros’ rebuilding playbook.

“Be like the Astros,” though, is much easier said than done. The Astros’ roster is stocked with some of the best players in baseball. And while the White Sox hope the same can be said about them within the next few seasons, is there more to the equation?

The Astros are one game removed from owning the best record in baseball. The White Sox and any other rebuilding team can emulate the way the Astros built their championship-caliber roster. But can the players on the field emulate the Astros, too?

“They play the game the right way,” White Sox catcher James McCann said Tuesday. “Guys hustle down the line. They protect the ball, they don’t make a lot of errors. And you can see the fun that they have on the field in their highlights.

“There’s a confidence, an aura about their team that they give off that is something that every team should look at. I know there’s a fine line between being cocky and arrogant and being confident. They’re definitely a confident team.

“You look at teams and you look at where they are and their expectations, and the natural thing to do is make comparisons. They went through the rebuilding process however many years ago, and obviously now they’re beyond that. But there’s definitely things you can take from every team, and they’re one of those teams that we can definitely take some things from.”

While every team has a window, the Astros have kept adding fuel to their burning contention fire. Rookie slugger Yordan Alvarez has been one of baseball’s best hitters since his big league arrival earlier this season. They went out and traded for Greinke at the deadline. All that after signing Michael Brantley to be one of their everyday outfielders last offseason.

The White Sox minor league depth doesn’t look quite as impressive as it did a few months ago, but there’s at least one more huge name down in the lower levels of the organization in Andrew Vaughn, the slugging first baseman selected in this year’s draft. He doesn’t figure to be joining the big league club two years after a World Series run like Alvarez and the Astros, expected here sooner than that, but he could be another member of that core that comes up and has a huge impact. The White Sox, too, expect one day to be the kind of team that makes big free-agent splashes and swings a pennant-race-altering trade at the deadline, too.

It’s important to note, obviously, that the Astros have reached the top of the baseball mountain and the White Sox are trying to get there. But the South Siders have the ingredients to write a similar rebuilding success story. Time will tell if they’re able to, of course.

But for White Sox fans wondering what all this waiting is for, just look across the field this week. That’s the endgame.

“It is at times a reminder,” McCann said, “to see, ‘Hey, we keep pushing and this is the eventual result.’”

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