[jksander]

2029 Season: We started typically slow, which is not a shock for Cubs fans in general, but by mid-June we found ourselves quickly heating up, with a 37-28 record and a growing lead on Pittsburgh, who sat 2.5 games back on June 11. At that point we worked out a trade that sent Corbin Burns (retain: 25%) to the Phillies in exchange for RHP Hunter Greene and minor league right fielder Kala’I Rosario. Burns has been struggling and had requested a change of scenery, and Greene has good potential as a back-of-the-rotation starter at a more reasonable price (the deal adds $5.5 million to our budget room, enough to help us as we search for an additional bat to fuel our quest toward playoff dominance). By draft day we’d improved our record to 54-37, with a 7.5 game lead on the Cardinals and a 9.5 game lead on Pittsburgh, and on the eve of the draft we pulled off a huge prospect deal with the Tampa Bay Rays that sent us second baseman Junior Caminero (.350/.404/.660 with 14 doubles and 27 homers and 4.7 WAR) in exchange for AA right handed pitcher DeMario Borrayo (#70 BNN), AAA center fielder Christian Franklin and A+ shortstop Lupe Garza, our second-rounder from 2027. The Rays are full-on in rebuild mode, and we’re loaded with prospects, so now seemed the time to really buy in.

We went on a flat-out tear from there as the whole team came together and took control of the division. We had a 12-game lead on the Cardinals when rosters expanded on September 1, our record at 78-56, and we clinched the division title by the middle of the month, cruising to a 95-67 record, the best of my tenure as GM by a game. Our nearest competitor in the division, St. Louis, finished 82-80 and did not make the playoffs. Junior Caminero finished with a team-high 41 homers, 112 RBIs and 105 runs scored, while PCA hit .284 with 27 doubles, 20 homers and 11 stolen bases, putting together another 5.0 WAR season. Yoshimatsu Ishida finished with a 17-9 record in his debut season, with a 2.73 ERA through 198.0 innings, striking out 193 with a 1.16 WHIP, while Justin Steele had his best record yet, going 19-7 with a 3.41 ERA, 212 K’s and a 1.17 WHIP through 224.2 innings, giving him 112 career wins at age 34. Rookie shorstop Arturo Malclonado, at the young age of 19, played in 140 games and hit .217 with 18 doubles, 12 homers and 49 RBIs, a 2.2 WAR season that was bolstered by an incredible +16.4 zone rating at shortstop through 1,223.1 innings ... with 178 putouts, 69 double plays and only 14 errors.

So bring on the playoffs! We were solid enough to not need to make a wildcard appearance this season, getting instead to wait on the results of a three-game series between the Diamondbacks and the Giants. It took three games, but the home-field Giants pulled it out. In the NLDS, we took game one 2-0 and game two 6-4, completing the sweep on the road with a 9-7 victory -- despite Justin Steele coming out of the game in the third inning, the bullpen held it together and Drew Rom (a player we picked up off waivers in April!) picked up the win. With four days to rest heading into the NLCS, we should have been fresh and ready, but they came out and beat us 5-1 on our field to start the series. We shut them out in game two, 2-0, Andrew Painter picking up his second playoff win with two hits, two walks and 10 K’s in a six-inning effort that Little saved. On the road in Atlanta, Drew Rom picked up his second bullpen win, 4-2, to put us ahead (with Little getting save number three), and though the Braves took game four 4-1, we won game five 6-2 and went back to Chicago ready to get the monkey off our back. Unfortunately we got shellacked in game six, losing 14-6 to the Braves as Painter collapsed, giving up six runs in 2.2 innings, putting everything on the line for a seventh game. We turned the tables on them with a 14-5 game seven blowout, securing our first trip to the World Series since 2016 with a 7.1 inning nine hit three strikeout five run effort by Steele that Wicks then closed out. Unfortunately we lost Moises Ballesteros for the remainder of the year due to recurring back spasms, which meant Connor Burns, our 70-rated backup catcher, was going to get a baptism by fire, with our rookie, Arturo Malclonado our only available backup in case of a calamity.

In the World Series against Detroit, we came out quickly and put them away 7-3 in game one, but lost game two in a 3-0 shutout. Detroit then took game three 8-4, but we won an epic game four by a 12-7 margin in 12 innings, scoring five runs in the final frame to absolutely crush them and evening the series at 2-2. We took a 3-2 series lead in game five by beating them on the road 6-4 as Painter picked up his third win of the postseason, but Detroit crushed us 10-2 in game six -- an eerie reminder of our game six collapse in the NLCS. All this added pressure to us in game seven at Wrigley on the first of November, but again we played our best ball under pressure ... Yoshimatsu Ishida pitched 6.1 shutout innings with one hit, one walk and six K’s, and Fraudy Maldonado, who signed a minor league deal with us back in April, won it for us in the seventh when Royce Lewis hit a two-run homer! Little got the save, his fourth, as we won this one 2-0 and took the championship.

This time it only took 13 years to bring a new title to Wrigleyville ... but can we keep the team together this time?
 
November 3, 2029: As you would expect, Tom Ricketts is through the roof excited about the title and the parade being prepared in our honor -- so much so that he’s extended my contract with the team for another three years at $2.2 million per! Luke Little is the biggest name on our roster who, if we can’t get a deal made, will be on his way out -- from his humble beginnings in 2020 as a fourth-round pick, Little has become the best closer in the game, saving 181 games with a 3.26 ERA, striking out 674 and putting together 12.0 WAR as a reliever. He made $16.8 million this year in his final arb year, and though other closers may be available on the market this offseason, he’s the best and the youngest. So we’re doing what we can to get an extension through.

November 4, 2029: We’re sending the following players to the Development Lab for the offseason:

3B Mike Bresser (AA) ... Gap Power
CL Haywood Darrach (Rookie) ... Secondary Pitch Improvement
2B Jon Wall (Rookie) ... Gap Power
RF Benny Grafer (Rookie) ... Plate Discipline
C Jose Flores (Rookie DSL) ... Improve Defense at Catcher
SP Chris Stout (Rookie ACL) ... Improve Control

November 10, 2029: It’s unfortunate, but Luke Little has broken off negotiations with us, wanting a far bigger payday than I’m willing to extend to a reliever, even as good as he is. We’re going to offer him a one year Qualifying Offer ($18.9 million) but it’s unlikely he’ll accept it. At the least, we should get a compensatory pick from whoever does decide to give him that big payday. In the interim we’ll be able to look for a stopgap closer in free agency or promote from within.

November 12, 2029: Luke Little was named Reliever of the Year, which I expect is going to drive his price up even further. At age 29, he made 57 relief appearances and picked up saves in 38 of them, opponents hitting just .206 against him which helped him to a 2.04 ERA. He’s wanting a contract with at least seven years and $300+ million attached, however, which is just too rich for my taste.

November 14, 2029: Yoshimatsu Ishida was named Rookie of the Year, with 26 first place votes out of a possible 30, finishing with more than double the points of his nearest rival. He had a 17-9 record through 33 starts, with a 2.73 ERA and 193 K’s against 50 walks. That ten year deal is looking better every day! To think, he’s just turned 24 ...

November 25, 2029: As expected, Luke Little rejected our QO and will be filing for free agency. Moises Ballesteros got an arb contract north of $21 million for this year, his final arbitration year, and Tom Ricketts is insistent that we get him resigned ... at 26 he’s one of the rare solid catchers who can both field and hit. Right now he’s asking for $31 million for a one year extension, or for $311 million over a seven year deal. I’m hopeful we can find numbers somewhere in the middle, but this is one I’ve got to make happen if I’m going to keep a good relationship with my owner (who has been willing to spend money so I want to keep him that way!)