Chuck Garfien's top five free agents the White Sox should target this offseason

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At the end of the 2017 Winter Meetings, I asked Rick Hahn a question that has been brewing around the White Sox ever since they started the rebuild two years ago.

How much are you thinking about the big free-agent class of 2018 when things can really get exciting for the White Sox?

“It’s certainly been on our minds. It’s been discussed, “ Hahn replied that day. “We expect things to be a lot more interesting a year from now.”

How interesting will it get? We don’t know for sure. A lot might depend on how much they believe their prospects developed in 2018, as Hahn explained in the same interview.

“A year from right now, we’re going to know a lot more about the timelines of (our) prospects,” Hahn said. “Which ones are more likely than not to be able to contribute sooner rather than later and reach their ceilings, and where in the organization we are going to have some depth that perhaps has to be moved or to fill in either via trade or via free agency. So we’re going to know a lot more a year from now about how quickly we’re going to get to where we want to be.”

To which I responded, “So, you’re going to sign Manny Machado?”

Hahn laughed.

Well, here we are. The next offseason has arrived for the White Sox. Here are some free agents who will be great fits for the White Sox next season and the future. Some are home run swings, others are singles and doubles. The first one is the grand slam.

1. Third base: Manny Machado

This is the dream scenario, probably a pipe dream, but Machado checks all the boxes for the White Sox. He’s a 26-year-old superstar, a charismatic franchise player coming off the best season of his career. Though he has stated his desire to play shortstop, Machado says he will play third base “for the right team,” according to Jon Heyman of Fancred Sports.

The White Sox have very little on the books over the next five years. If they want to pay him $40 million a year, they have room to do it. Is it wise to give that much money to a single player who would represent 40 to 50 percent of your entire payroll? Probably not, but players like this rarely become available. His signing would plant a flag and send a message to the rest of the league that the White Sox have arrived. Baseball would be electric on the South Side. In theory, it’s a no-brainer. In reality, he’s probably signing with the Yankees. But you can dream!

Backup plan: Josh Donaldson

Donaldson’s market will be interesting to watch this winter. He’s coming off two injury-plagued seasons (played in a total of 165 games), but when healthy he’s one of the best hitters in the game. He will be 33 years old and made $23 million in 2018. Nolan Arenado and Anthony Rendon are set to be third base free-agent options in 2020, so keep that in mind. The White Sox don’t have much on their payroll for next season. If Donaldson is willing to sign a one-year deal to prove he’s healthy, play in a hitter-friendly ballpark in the American League and try for a bigger contract the following season, I’d pounce. He’s an immediate difference-maker in the lineup. You make Yolmer Sanchez a super utility guy. Daryl Boston can blow his whistle at Donaldson to celebrate the signing.

2. Outfield: Adam Jones

When I asked Eloy Jimenez in 2017 on the White Sox Talk Podcast how good of a baseball player he wanted to be, he answered, “Like Miguel Cabrera, Mike Trout, Adam Jones. Superstars. That is my dream.” If Jimenez thinks that highly of Jones, why not sign the free-agent outfielder to a one- or two-year deal and let him mentor the White Sox future star? Jones will be 33. He had 15 home runs and 63 RBIs in 2018, his lowest totals since 2008, but he’s one of the most respected players in the game and will bring the White Sox added value for what he brings off the field. Former Orioles manager Buck Showalter said this about Jones this season: “His example of how to play the game has meant more than anything.” The White Sox will have a bunch of young outfielders coming up from the minors over the next couple years. I can’t think of a better veteran to have on the roster to show them the way than Jones.

Backup plan: Curtis Granderson

The South Suburbs native keeps on truckin’. At 37 years old, he slashed .242/.351/.431 in 2018. Like Jones, he’s cut from the James Shields leadership cloth. He made only $5 million this year. He can play in front of his friends and family. You can have UIC Night at the ballpark. Sounds like a win-win.

3. Starting pitcher: J.A. Happ

With Michael Kopech not back until 2020 and Shields a free agent, the White Sox have two spots to fill in the rotation. As great as it would be to sign someone like Dallas Keuchel or Patrick Corbin, a smart plan here is to sign a veteran like Happ as a bridge to when you have pitchers like Kopech, Dylan Cease and Dane Dunning ready to compete in the majors. After the Yankees acquired him from the Blue Jays this summer, Happ went 7-0 with a 2.69 ERA. That might keep him in New York, but if they’re trying to sign Machado and either Corbin or Keuchel, even the Yankees might not have money left for Happ.

Backup plan: Gio Gonzalez

He was drafted by the White Sox, traded by the White Sox (for Jim Thome), acquired by the White Sox (for Freddy Garcia), traded again by the White Sox (for Nick Swisher). Why not come full circle and sign Gonzalez as a free agent? Then trade him again. Seriously, he would be a solid option for the rotation. He finished sixth in Cy Young Award voting in 2017.

4. Relief pitcher: Adam Ottavino

The White Sox currently don’t have a true closer in their bullpen. They might not contend in 2019, so spending big money on a closer wouldn’t be the most prudent decision to make from that standpoint. However, there are a bunch of free agents available this offseason (Jeurys Familia, Craig Kimbrel, Cody Allen, Greg Holland, Kelvin Herrera, etc.) and fewer options are expected on the market next offseason. Do the White Sox go all-in on a closer this winter so they’ve got someone reliable at the back end of the bullpen for 2020 and beyond? Tough call. Not just for a closer, but for setup men, too. These are tough, risky waters to swim in. Hahn knows it.

“The prices to go out and build a good, proven bullpen right now are awfully steep. That’s coming for the White Sox in the coming years. That’s the part that scares me,” Hahn said in our interview at last year’s Winter Meetings. “We’ve got to be right on those. When you’re betting $14 to $20 million on a seventh-inning guy, you better be right.”

From an age standpoint, Familia makes sense because he’ll only be 29 years old next season. His 1.8 WAR is the second highest among relievers in this free-agent class, second to Ottavino’s 2.0. Familia had 51 saves in 2016. But is he the pitcher you want to hitch your wagon to for the next four years? Maybe.

To me, the safer bet is Ottavino, who wasn’t the Rockies' closer last season (he had six saves) but definitely has closer stuff: 112 strikeouts in 77.2 innings. He also had a 2.10 ERA in 34 innings at Coors Field. The dude throws filth. He’ll be 33 years old, so he’s probably not a long-term answer. The White Sox could make Ottavino the closer until one of the young arms like Zack Burdi is ready. If that doesn’t work out, trade a prospect to get a closer by 2021. I agree with Hahn. The high-end bullpen market scares me.

Backup option: Familia

5. Can’t beat him, sign him: Michael Brantley

Brantley is exactly the kind of hitter the White Sox need: a patient, on-base guy who doesn’t strike out (60 in 631 plate appearances in 2018), is left-handed, can hit for power and is a doubles machine. In 17 games against the White Sox in 2018, he slashed .343/.400/.567 with four home runs. Because of his injury history, will he get anything more than a two-year deal? That’s the question. Try to sign him for two years as a bridge until all your outfield prospects are MLB ready, bat him second behind Yoan Moncada and in front of Jose Abreu and Eloy Jimenez and watch this offense take off. He’s a hitter who makes everyone around him in the lineup better. The Indians' offense would be worse without him. Another win-win.

Backup plan:  Eduardo Escobar

Ever since the White Sox traded him to the Twins for Francisco Liriano in 2012, Escobar has seemingly made it his mission to make the White Sox pay for it, especially this past season: .333/.423/.733 with four HR and 11 RBIs in 12 games. Thankfully, the Twins traded him to the Diamondbacks at the deadline to limit the damage. Now he’s a free agent, he’s coming off a career season, and he can play third base. Honestly, I’m just hoping he signs with a National League team so the White Sox only have to face him in Interleague play.

So there you have it. My free-agent targets for the White Sox. It’s much easier to write about free agents than sign them. We don’t know how aggressive the White Sox will be this offseason, but one thing seems certain: That day is coming. Stay tuned.

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