Keuchel has three-year deal with White Sox (source)

After remaining unsigned until after the MLB Draft in June, Dallas Keuchel is hoping for a better result as he tests the free-agent market again.

Below is a list of the latest news and rumors surrounding Keuchel, who will turn 32 years old in January.

Keuchel to White Sox on three-year deal (source)

Dec. 21: The White Sox and Keuchel have agreed on a three-year, $55.5 million deal, a source told MLB.com's Mark Feinsand. The contract will include an option for a fourth year that would take the total value up to $74 million. The club hasn't confirmed the agreement, which was first reported by ESPN's Jeff Passan. More >

The agreement with Keuchel comes a day after the White Sox made official their signing of fellow left-handed starter Gio Gonzalez. Chicago also made a splash earlier this offseason by inking catcher Yasmani Grandal to a four-year, $73 million contract.

Angels, White Sox both add starters

Dec. 19: The Angels and White Sox were thought to be two of the top suitors for Hyun-Jin Ryu and Keuchel, but both clubs added veteran starting pitchers on Thursday, with the Halos reportedly agreeing to a deal with Julio Teheran and Chicago picking up Gio Gonzalez.

According to MLB Network insider Jon Heyman, Los Angeles hasn't ruled out adding another starter, but it's unclear how aggressive the team will be in pursuing one.

In any case, the Angels have more leverage in negotiations with agent Scott Boras, who represents Ryu and Keuchel. Their rotation current rotation consists of Andrew Heaney, Shohei Ohtani, Dylan Bundy, Griffin Canning and Teheran.

As for the White Sox, Bruce Levine of 670 The Score reports that the Gonzalez move doesn't take Chicago out of the running for Ryu or Keuchel. The White Sox rotation projects to be Lucas Giolito, Reynaldo López, Dylan Cease, Michael Kopech and Gonzalez, so they arguably have an even greater need for one of the two free-agent lefties than the Angels.

Feinsand: Boras is 'deep in negotiations' for Keuchel, Ryu

Dec. 18: The big-name pitchers who made up the top tier of free-agent starters already have signed long-term contracts. Keuchel and fellow southpaw Hyun-Jin Ryu are pretty widely considered the best options still available, and a number of teams remain in need of rotation help. That puts the duo in a good position to secure their own multiyear pacts.

Two keys to remember with regard to these veterans? Neither is tied to Draft-pick compensation and both are represented by Scott Boras, who has had a huge impact on this offseason by getting massive deals for clients Gerrit Cole ($324 million), Stephen Strasburg ($245 million) and Anthony Rendon ($245 million), among others.

As for Keuchel and Ryu, although Boras didn't specify which teams are in on each, he did say he's "deep in negotiations" for both, according to MLB.com's Mark Feinsand.

So which clubs could that apply to? For Ryu, the Rangers, Blue Jays, Angels, Cardinals, White Sox, Twins and Dodgers (the only MLB team he's pitched for to date) have been linked. The list of interested parties for Keuchel also includes the Angels, Cards and White Sox, as well as the Padres and Cubs, per Feinsand.

Keuchel, in particular, could be a target for the Twins, who have been connected to just about every starter so far but have yet to add a new arm; the club has brought back Jake Odorizzi (on the qualifying offer) and Michael Pineda, leaving a need for up to two more starters. Eno Sarris of The Athletic (subscription required) suggests a four-year, $80 million deal could put Keuchel in Minnesota.

Padres looking at Keuchel among top remaining pitchers

Dec. 13: The Padres are among teams looking at Keuchel, according to a report from MLB Network insider Jon Heyman. There were indications that the Padres might not be in on the bigger free agents, Heyman notes, but they are attempting to be competitive in 2020. They steered clear of the two successive record-breaking deals for pitchers given to Stephen Strasburg and then Gerrit Cole, but the $100 million figure hasn't even been thrown around yet regarding Keuchel, who signed in-season last year and only made 19 regular-season starts.

*Keuchel a fit for pitching-hungry Halos? *

_Dec. 13_: At this week's Winter Meetings in San Diego, the Angels came up short in the Gerrit Cole sweepstakes but snagged Anthony Rendon to back up Mike Trout in their lineup. That was a big step, but there is no question the club still needs rotation help.

With Cole, Stephen Strasburg, and Zack Wheeler off the board, is Dallas Keuchel the answer?

MLB.com's Richard Justice, appearing on MLB Network's "Hot Stove" on Friday morning, believes that the left-hander will at least be an answer for the club. While stating that the Angels still need multiple starting pitchers, Justice predicted, "I think Dallas Keuchel is gonna end up in Anaheim."

As Justice pointed out, he is far from the only option. Fellow lefties Madison Bumgarner and Hyun-Jin Ryu are free agents, while Boston's David Price and Detroit's Matthew Boyd are potential trade targets. Multiple reports have indicated that the Angels also have held trade discussions with Cleveland for righty Corey Kluber.

But with Rendon in the mix, playing next to defensive wizard Andrelton Simmons, a ground ball specialist such as Keuchel could be even more appealing. The 2015 AL Cy Young Award winner ranks second in the Majors in ground ball rate going back to that season while averaging 173 innings per year.

*A shorter winter in the cards for Keuchel *

_Dec. 13_: A year ago, Keuchel waited, waited and waited some more, languishing on the open market until the Draft arrived, freeing interested teams from losing a pick in exchange for bringing him onboard. Keuchel finally inked a one-year deal with the Braves on June 7.

The left-hander's outlook this time around is considerably rosier, even if he has not been one of the first starting pitchers to land a new deal. But Keuchel makes MLB.com executive reporter Mark Feinsand's list of the major free agents likely to sign next.

"It still might take weeks, but after signing last June following a frustrating winter, Keuchel should have a deal long before Spring Training starts in February," Feinsand concludes.

Keuchel is a client of Scott Boras, who has been extremely busy of late negotiating monster deals for Gerrit Cole, Stephen Strasburg, and Anthony Rendon. Now that those are done, and with Zack Wheeler and Cole Hamels also off the board, Keuchel is in the next group of pitchers available, along with Madison Bumgarner and Hyun-Jin Ryu. Feinsand posits that K

Ryu, Keuchel could be Angels' fallback options

Dec. 6: The Angels are among the clubs that have met with Gerrit Cole and Stephen Strasburg already, along with the Yankees and the Dodgers. And given the state of the Angels' rotation, the club arguably has a greater need to sign one of the free-agent aces than the Yankees or Dodgers.

Currently, the Angels' starting staff consists of Andrew Heaney, Shohei Ohtani, the newly acquired Dylan Bundy and a bunch of question marks.

If the team strikes out on both Cole and Strasburg, it's interesting to wonder where general manager Billy Eppler would turn next. In an article for ESPN+ (subscription required), Buster Olney suggests that the Angels would consider Keuchel, Hyun-Jin Ryu and/or Madison Bumgarner. Bumgarner, though, may be off the market by then, which means the Angels' best options could be Ryu and Keuchel.

What does Hamels signing mean for Keuchel?

Dec. 4: Free-agent starting pitchers are starting to come off the market. The big news Wednesday was Zack Wheeler agreeing to a $118 million deal with the Phillies. But it was the first starter to sign that might have the bigger impact on Keuchel's future.

That would be fellow veteran left-hander Cole Hamels, who inked a one-year, $18 million contract with the Braves -- Keuchel's 2019 team.

MLB.com's Mark Feinsand writes how Hamels' deal might mean that Keuchel's time in Atlanta is over. But there should be other suitors, especially now that Keuchel doesn't have the Draft pick compensation tied to him that he did last offseason, when he declined a qualifying offer from the Astros.

Feinsand suggests that teams like the Blue Jays, White Sox, Twins and Reds could be among those that pursue Keuchel, even if the Braves don't. More >

Morosi: Blue Jays eyeing Keuchel and Ryu

Dec. 3: The Blue Jays have a nice young core of promising position players, headlined by the likes of Vladimir Guerrero Jr., Bo Bichette and Cavan Biggio, among others. If they want to get back to contending in the competitive AL East in the near future, however, it's going to take an upgrade to the rotation.

That's where Keuchel and fellow lefty Hyun-Jin Ryu come in.

Both pitchers are "possibilities for the Blue Jays," MLB.com's Jon Paul Morosi said in a Tuesday appearance on MLB Network's Hot Stove show. "Because of where the overall starting pitching supply is going to be next winter, it makes a lot of sense for the Blue Jays to court both Ryu and Keuchel now. And I'm told both are on their list."

In other words, this year's crop of free-agent arms is shaping up to be deeper and more impactful than next offseason's batch. It might behoove the Blue Jays to act now, even if they aren't clearly ready to contend yet.

Morosi added that Toronto could benefit from bringing in a veteran starter or two to help shepherd the club's young arms -- like Sean Reid-Foley and Trent Thornton, as well as prospects Nate Pearson, Anthony Kay and T.J. Zeuch -- as they transition to the big leagues.

MLB Network insider Ken Rosenthal also had the Blue Jays on his list of Zack Wheeler suitors in a story for The Athletic (subscription required).

Keuchel may be in Cubs' wheelhouse

Nov. 30: The Cubs don't appear to be involving themselves in the sweepstakes for Gerrit Cole or Stephen Strasburg, writes The Athletic's Patrick Mooney, nor do they seem poised to make a run at Zack Wheeler, Hyun-Jin Ryu or Madison Bumgarner. But, Mooney writes, the Cubs know they need to add starting pitching, and a pitcher like Keuchel may be exactly the type they're going for. He notes that Keuchel is a former American League Cy Young Award winner.

“It depends on moving parts,” Mooney quotes Theo Epstein as saying. “It’s an area in free agency that’s fairly robust this year — the depth of starting pitching options — maybe even more so than the relief market. It’s usually the other way around, so I think you have to be open-minded.”