Castellanos, Hamels Headline Former Cubs Among MLB’s Top 50 Free Agents Expected to Find New Teams

Our focus to this point in the offseason has been on which free agents the Cubs could and should target, which is kind of par for the course given the whole purpose of this site. But as I just learned recently, there are actually 29 other teams out there seeking new players, which means it may not simply be a matter of the Cubs choosing whether or not to pursue someone.

I’ll give you a moment to compose your if this revelation has left you somewhat shaken.

Ready to continue? Okay, good, I promise to avoid subsequent metaphorical blows to your solar plexus as we move forward here. Anyway, my point is that the Cubs aren’t going to bring back fan favorites just because you/we want them to. And in some cases, those players might actually feel as though the grass is greener elsewhere.

Damn, and here I said I was going to avoid another emotional shot. Unless you’re talking about an angry Gerrit Cole donning his Boras Corp. hat and telling the media he was unemployed immediately after the conclusion of the World Series, most players are going to speak glowingly of their former organization and express hope for a return.

Remember when Jesse Chavez told reporters in 2018 that he’d rather retire than pitch in anything other than a Cubs uniform the following season? Well, he was right back in Texas a couple months later because the Rangers gave him a two-year deal when the Cubs were only willing to go to one. The same could be true this year for several free agents who’ve either expressed a desire to return or who’ve performed well on the North Side.

In their list of the top 50 free agents, MLB Trade Rumors predicts where and for how much each will sign. So while they’ve got pitchers Kyle Gibson and Will Harris joining the Cubs, four other players could be donning new uniforms next season.

Nicholas Castellanos, White Sox – 4 years, $58M

There’s reportedly mutual interest between Castellanos and the Cubs, but he’s also interested in maximizing the value of his late-season power surge as he heads into his age-28 season. He shares an agent with Cole, not to mention at least four other members of the consensus top 15 free agents this winter, and isn’t likely to sign quickly unless some team blows him away with a big offer.

Though he showed that he wasn’t as much of a butcher when playing in Wrigley’s cozier outfield, Castellanos’ market me be somewhat limited by his substandard defense. And just in case you’re thinking that a move to third base would be intriguing to the Cubs — or any team, for that matter — you need to understand that there’s a reason Castellanos is playing a corner outfield spot.

While his passionate talk of being reinvigorated by the trade that brought him to the Cubs was entirely genuine, Castellanos is going to want to see what moves the team makes to get better this winter. So even though the situation at Wrigley was perfect for him in August and September, circumstances may dictate otherwise in December or January.

The FanGraphs estimates on Castellanos came in at four years and $56 million, which seemed a little light. MLBTR isn’t much higher, giving him an extra $2 million to remain in Chicago and move just a few miles south. Having the DH gives a little more flexibility, especially with a team that might be willing to outbid others after initially pining for J.D. Martinez before he chose to remain in Boston.

Cole Hamels, Braves – 2 years, $30M

It’s still possible for the Cubs to work something out with the 35-year-old lefty even after choosing not to extend him the qualifying offer, but it’s not going to be anything close to the two years and $30 million MLBTR projects. The Braves are reportedly prioritizing another veteran southpaw, Madison Bumgarner, so perhaps Hamels’ market doesn’t quite materialize.

He made it a point after the season to talk about how much he liked pitching at Wrigley, even going so far as a to openly court other NL Central teams. With the Cardinals reportedly trying to maintain the same payroll and neither the Reds nor the Pirates really looking like contenders, might the Brewers make sense? They’ve certainly lacked pitching depth and could see Hamels as a steadying force.

But when it comes to emotional ties, Hamels’ strongest are to the Phillies. That’s where he had his best years and won a World Series before being traded to Texas, so there’s probably a sense of unfinished business or nostalgia. As the lefty recently told Todd Zolecki of MLB.com, he’s very much interested in a return to Philly and is willing to continue his career on a series of one-year deals.

“I’m not there to handcuff somebody or an organization,” Hamels said. “That’s what the younger guys can do. I can do one year here and there and just play as long as I can play. I think that’s what will help give me an opportunity to play on teams that are trying to go to the postseason. If you need one guy, I can just kind of bounce around. Obviously, if the Phillies were interested in longer than one, I’d entertain that, too. But I think I want the opportunity to have as many opportunities to get to the postseason and try to win.

“I’ll go every year. I’ll prove myself. I don’t mind having my back against the wall. I think I perform better like that anyway. It just keeps me more accountable.”

Steve Cishek, Diamondbacks – 2 years, $10M

This prediction makes all the sense in the world because Cishek needs to get into the dry desert air after being ridden hard and put up wet for three seasons in Chicago. Oh, it was only two seasons? Guess it just seemed like more because he appeared in 150 games for the cubs.

After pitching 80 times in 2018, 11 more than his previous career high, Cishek took the mound 70 times this past season. That despite a hip issue that landed him on the IL, something that probably should have been a more serious concern for a sidewinder whose delivery puts undue stress on a hip in which he’d previously suffered a torn labrum.

His strikeouts were down, his walks were up, and he turned 33 in June. More power to him if a team sees fit to hand him a couple years, but Cishek is one of those guys the Cubs should be able to replace with a younger arm.

Pedro Strop, Red Sox – 1 year, $5M

Man, this one is tough because Strop has been the Cubs’ best and most consistent reliever since coming over from Baltimore with Jake Arrieta. As such, the deal actually would have been a huge coup for the Cubs even if the 2015 Cy Young winner had never pitched for them. Lost in what was otherwise a disappointing season is that Strop actually posted a 10.48 K/9 in 2019 that’s more than a full K above his career average.

His spotty health limited him to his fewest appearances (50) and innings (41.2) since 2011, however, and his 4.97 ERA was the worst of his career. What’s more, Strop’s 93.6 mph fastball velocity was lower than ever and led to fewer missed bats. Perhaps worst of all is that those who’ve unfairly maligned him over the years felt justified by the dropoff.

There’s potential for a reunion if Strop is willing to take an incentive-laden deal to essentially serve as the de facto captain of the bullpen. A vocal team leader, his value would be more in showing the young guys the ropes than in holding down the late innings. If a team is going to offer him $5 million, he might need to see if a change of scenery spurs a rebound.

Several other former Cubs may also be in new uniforms next season, including David Phelps, Brandon Kintzler, and even Ben Zobrist. But since they’re not among the top 50 free agents, there just weren’t any predictions for me to bump up against. As with anything, return engagements are going to be a matter of money and comfort, the first of which will almost certainly have priority over the latter for both sides.

Other than Castellanos, it’s possible some of these other guys start finding new homes pretty soon in order to avoid the anxiety of a drawn-out winter. Between that and MLB really wanting to showcase its own offseason in the same way the NBA and NFL do, I’d anticipate this year’s Winter Meetings featuring a lot more meaningful activity.