Sorry Tom, free agents aren't actually free

A look at the top 20 free agents and who the Cubs should and might sign

Sorry Tom, free agents aren't actually free

Free agency has technically started, but it won’t really get going until after the November 15 qualifying offer deadline, and honestly, nobody good signs until January these days. But hey, it’s never too early to rank some free agents!

For the purpose of this pointless exercise (hence, the name of the newsletter) we’ll rank the top 20 players based on who will have most impact (regardless of cost—sorry Tom)…

…on their new team, and let’s figure out how attractive they should be to the Cubs and how likely they are to actually make them a real offer.

  1. Aaron Judge, OF - Judge, you may have heard, just hit 62 home runs last year and nearly won a triple crown. Yankee Stadium isn’t a difficult place to hit homers, but the beauty of Judge playing at Wrigley is long home runs are more impressive there because you get to hit other Ricketts owned buildings with them. You know Tom would put a bill for any broken windows in Judge’s locker. He turned down a seven year extension at about $30 million per from the Yankees last spring, so he’ll want eight years at about $35 million. He’s 31, so you’re paying him until he’s almost 40, but he can probably still handle center for a couple more years and then a corner and then eventually DH and what do you know, the National League uses all of those things.
    Will they make him an offer? Almost certainly no.
    Chances they actually sign him? What’s less than zero?
  2. Trea Turner, SS - Here’s the beauty of baseball. Turner is nearly as good as Correa and he plays almost nothing like him. He’s a good, but not great defender and a really good hitter and a great baserunner. He will age into second base at some point and the Cubs don’t have anybody over 5’1 on their roster to play there. So Trea plays short for a few years with Nico moved over to second and then they switch at some point.
    Will they make him an offer? Yeah, they probably will.
    Chances they actually sign him? 12.7%
  3. Jacob deGrom, SP - Remember in 2014 or 2015 when there were rumors the Cubs were going to trade Javy Baez to the Mets for deGrom? It would have been a great trade, and yet, I’m glad it never happened. Because we saw the Cubs win with Javy, and given their history with pitchers, deGrom would have started his Cubs career 7-1 with a 0.89 ERA and then had six Tommy John Disease operations over the next six years. deGrom will be an interesting free agent. When healthy he’s a $50 million a year pitcher, but he’s hurt a lot, and he’s 35. He’s going to get a lot of short (three year) offers for a lot of money. I don’t think the Cubs will be one of those teams, and honestly, as much as I’d love him to pitch for them, it’s probably the right decision.
    Will they make him an offer? Nope.
    Chances they actually sign him? 0.0
  4. Xander Bogaerts, SS - Of the big three (plus Dansby Swanson) shortstops in this class, Xander is the best pure hitter. He also is the worst shortstop. If the Cubs signed him they shouldn’t even bother with the ruse of playing him at short for a while to justify the contract before moving him to third. Just put him there right away and leave Nico alone. Given all that, he might be the best buy. He’ll be expensive but the thing he’s best at, he figures to be best at for a long time. Plus, he has a cool name. That has to count for something. I think of the three shortstops, he’d be the one I’d sign, even if he never actually played short for me.
    Will they make him an offer? Yes. I think they’ll start with Correa, get scared and talk themselves into Bogaerts.
    Chances they actually sign him? 51%
  5. Carlos Rodon, SP - First, the good about Carlos. He’s really good now. He’s a power pitcher who can carry his stuff deep into games and as a bonus he’s a lefty. The bad stuff? The Giants will give him the qualifying offer (it’s at least half the reason they signed him in the first place), he’s been injury prone and he’s only been good for two years. So either he’s a late bloomer who you’ll be buying for most of his peak, or he’s really good when he’s completely healthy and won’t be that very often. The Sox didn’t give him a QO last year because they were afraid he’d accept it. But then, they’re morons.
    Will they make him an offer? Yes.
    Chances they actually sign him? 27%
  6. Justin Verlander, SP - He’s forty and fabulous and his breasts have never looked firmer. What? Never mind. Verlander says he wants to pitch long enough to get 300 wins, and he’s currently at 244 wins, 245 if you count his nine World Series starts. (Zing!) So that’s realistically what, four more years at least? He just had Tommy John Disease two years ago, but then again, he had a 1.75 ERA this last season. The good news is you get his wife, the comely Kate Upton, the bad news, you probably get his idiot brother, too, and you just know Marquee would hire that dolt. He’s five years older than deGrom, but is he somehow a safer bet? He probably is.
    Will they make an offer? They could have claimed him on waivers and kept him from going to Houston in 2017. Instead they didn’t and he went 61-19 with a 2.26 ERA for the Astros. Nice job, Theo.
    Chances they actually sign him? I think this might happen, let’s say 48%.
  7. Willson Contreras, C - The fact he’s a free agent is just bullshit. The Cubs could have resigned him and never did, they tried to trade him twice and they wimped out both times, and now they will torpedo his one shot at a big payday with the qualifying offer. But hey, at least they’ll get a compensatory pick from the Cardinals for him. (Sobs into a pillow.)
    Will they make him an offer? No. They never have.
    Chances they actually sign him? What do you think?
  8. Kodai Senga, SP - Last spring Tom Ricketts and Jed Hoyer supped with Seiya Suzuki, and Tom charmed Seiya into signing. I know, can you imagine? What did Tom do, the severed finger trick? Did he pull a quarter out of Seiya’s ear? If he did, I’m sure he kept it. Anyway, they have another chance this year to woo a Japanese star, and like Seiya this one would be a perfect fit. Senga throws really hard, he just doesn’t always know where it’s going. There’s a little concern he won’t stick as a starter, but at worst he’d be a back of the bullpen fireballer, and it’s likely he makes it as a starter. He’s cut his walks dramatically the last couple of seasons and he throws 99-102 at the top end and “sits” (baseball term) 96. Plus, somebody tell Tom that Kodai and Seiya can share an interpreter.
    Will they make him an offer? Yes.
    Chances they actually sign him? I think the Cubs or the Giants are the most likely to sign him, and I actually think the Cubs will. 75%
  9. Brandon Nimmo, CF - He’s a perfect fit for what the Cubs need. He plays a good center field, he gets on base a lot, he’s a lefty hitter, in the only two seasons he’s ever played at least 140 games he’s averaged 16.5 homers, he led the NL in triples last year and he gets hurt a lot. Wait, that last one’s probably not a plus. Although, what if he runs into the bricks at Wrigley in three years when Pete Crow-Armstrong is ready to take over center and insurance pays for his wheelchair?
    Will they make him an offer? Yes.
    Chances they actually sign him? 61.3%
  10. Clayton Kershaw, SP - Who gives a shit? He’s not leaving the Dodgers.
  11. Dansby Swanson, SS - There’s a pretty steep drop off from Bogaerts to Dansby. Like really steep. Swanson has hit 52 homers in the last two years, which is good, but he doesn’t get on base (.321 career OBA) and he strikes out a lot (182 times this past year.) So he’s like Javy without all the cool Javy stuff. Hard pass.
    Will they make him an offer? Probably.
    Chances they sign him? Too high.
  12. Anthony Rizzo, 1B - Our old pal just opted out of a $19 million 2023 deal with the Yankees to try free agency. He has routinely made poor contract decisions. Maybe Roquan is his agent? But this time he probably realizes while he’ll get less than $19 million, he’ll get two or three years and that’s likely what he wants. Does a return to the Cubs make sense? Yeah, it kind of does. They have nothing at first. He’s still a plus defender and has power, and two years of Rizzo won’t really block Matt Mervis as Mervis can DH or spend some more quality time in Des Moines. Rizzo still fucks up his back two or three times a year, so there are some built in Mervis games. A team will talk themselves into the idea that without the shift this season Rizzo’s numbers will go up. That might be a real thing. But the reality is that he hasn’t been able to hit a good fastball for about four years, and last year with the Yankees he just said “fuck it” and started cheating on them. And with the short porch there it worked out mostly. He’s a four outcome player now. Homer, strikeout, walk or lean into one and get hit by a pitch.
    Will they make him an offer? I don’t think they will. I don’t think they want to part with him a second time, which is what would have to happen at some point.
    Chances they sign him? I guess it’s possible, but not likely, say 12%.
  13. Jose Abreu, 1B - Most of what I just wrote about Rizzo applies to Abreu except Jose hits for a higher average and is a lot older, oh and he plays first base like a tree. Jose also cheats to get to fastballs, he’s just better at it. Given his age and his attractive defensive combination of bad hands and slow feet, the only reason to sign Abreu would be to piss off Sox fans. Honestly, that’s tempting, but they always find something to get pissed about anyway, so why bother? I do think the Cubs will kick the tires on this busted down old jalopy, though.
    Will they make him an offer? Likely, yes.
    Chances they sign him? I think he’ll end up back with the Sox, but how about 22%?
  14. Chris Bassitt, SP - This feels like a Cubs signing, doesn’t it? Bassitt had a good year for the Mets, he’s a little older than you’d like, he eats innings and keeps his team in games, he throws too many pitches (six) for his own good and the pitch lab dorks will eat that up. I think he’ll be a good signing for somebody. I also think the Cubs will think it over and over and then decide he’s a better version of Adrian Sampson but Sampson’s cheap, so they’ll just stick with him. And then be shocked when Adrian’s bad.
    Will they make him an offer? I could see it happening.
    Chances they sign him? 8% — They’ll talk themselves out of it.
  15. Tyler Anderson, SP - The Dodgers are everything the Cubs were supposed to be. They win, they develop young players while paying stars, and they use their fancy pitch lab to take reclamation projects and turn them into really good players. That’s exactly what they did with Tyler Anderson. Anderson started his career in Colorado and couldn’t wait to get the hell out of there for obvious reasons (altitude and mandatory bible study), showed promise in the pandemic year with the Giants and then after spending time with Pissburgh and Seattke in 2021 he got to the Dodgers and turned into an All-Star. He went 15-5 with a 2.57 ERA. He was good at home 8-2, 2.26 but also good on the road 7-3, 2.87. He was 10-1 in the first half and only 5-4 in the second, but he had a better ERA in the second half (2.10 v. 2.96) and a lower WHIP in the second half (0.987 v. 1.017). He’ll be 33 on opening day, but he’s a lefty so that’s like a 26 year old righty (whatever, just go with it.) You would think he’d really want to stay with the Dodgers, but I could see him being swayed by the Cubs’ nonsense about their pitch lab, too.
    Will they make him an offer? Maybe.
    Chances they sign him? I could see it. 48%
  16. Taijuan Walker, SP - When the big fella (6’5, 235…looks 6’9, 280) left the D’bags before the 2020 season the Cubs really wanted him and thought they were going to get him, but in the end he chose to go back to Seattke where he’d started his career. He ended up being traded to a surprisingly frisky Blue Jays team and pitched well but they lost in two games in the Wild Card Series to the Rays and he signed with the Mets, where he’s been pretty good. He was 12-5 with a 3.49 ERA this past year and he’s still only 29. You can easily see the Mets re-signing deGrom and Bassitt and some team snapping up Walker for far less.
    Will they make him an offer? Yes.
    Chances they sign him? 41.84%
  17. Jameson Taillon, SP - Taillon had a good year on a really good team, and for a guy with a lot of bad luck in his career (playing for the Pirates, going through cancer treatment, catching Tommy John Disease twice) he’s had a fair amount of success. For his career he’s allowed less than a hit per inning, he has 710 strikeouts to just 193 walks and his career record is 51-35 with a 3.84 ERA.
    Will they make him an offer? Maybe. The Yankees did the hard work and changed his pitch mix, but the pitch lab guys could probably find a way to take credit for it.
    Chances they sign him? 10%
  18. Michael Conforto, LF - Conforto had a fun year, didn’t he? He didn’t sign after the lockout and then it turned out he missed the entire season with shoulder surgery. He struggled in 2021 after a nice four year run where he hit .265/.369/.495 over four seasons from 2017-2020 with 97 homers even though one of the seasons was the 60 game COVID year. Because of his struggles in 2021 (were they early signs of his bum shoulder?) and the surgery and the fact that Scott Boras is his agent, he’ll be looking for a “pillow” contract and somebody could get a nice, fairly cheap season out of him before he tries to test free agency for real in 2024.
    Will they make him an offer? Not with the Gold Glover in left.
    Chances they sign him? Not much.
  19. Andrew Benintendi, LF - It’s easy to forget that Benintendi got traded to the Yankees at the deadline because he got hurt and didn’t play after September 2. He was the seventh pick in the 2016 draft and he was the guy the Cubs were going to pick. Instead they got Ian Happ two picks later. They’ve both been All-Stars once and Happ has that phony Gold Glove now. Anyway, Conforto and Benintendi being his high on this list shows how few good outfielders are on the market this year. He’s tiny (5’9, 170) and he hit 20 homers in 2017 but only 51 in the five years since. Teams in need of outfielders would be wise to call the Cubs and offer lots of prospects for Happ. Right? Ahh, never mind.
    Will they make him an offer? No.
    Chances they sign him? Zip.

Carlos Correa, SS - The Cubs should have signed him last year but they didn’t want to pay him, they wanted to tank, and they didn’t want to lose a precious draft pick. This time around they still would have to pay him, but they shouldn’t still be tanking and he no longer will have draft pick compensation attached to him. He’s only 28, he’s a consistently excellent offensive player, he’s a bonafide shortstop and as he ages he figures to be at worst a plus defender at third base. And that’s important considering it’s going to take a ten year deal to sign him. Tom, are you OK? Did you fall off the chair? Jed, get him some Dasani.
Will they make him an offer? Actually, probably yes.
Chances they actually sign him? I think they might do it. I’ll put it at 38%.