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The 1990 season was not a banner year for the Yankees. The team lost 95 games, the most in their entire history (if you don’t count some moribund Highlanders squads around the turn of the previous century). Their manager, Bucky Dent, made it through only 49 games before getting the boot. Don Mattingly, struggling with back injuries, hit just five home runs. Tim Leary, the team’s best-performing pitcher, led all of baseball in losses (19) and wild pitches (23). Their brightest spot was a homegrown player coming into his own, playing elite center field defense while swiping 42 bags and appearing in all 162 games on a roster decimated by injury. By the time the Yankees returned to the mountaintop six years later, he’d be gone, but his ascent remained a critical piece of the team’s rebuild.

Roberto Conrado Kelly
Born: October 1, 1964 (Panama, Panama)
Yankees Tenure: 1987-92, 2000

Roberto Kelly grew up in Panama City, where he impressed from a young age with his athleticism. Fred Ferreira, the longtime scout who also signed Bernie Williams and Hall of Famer Vladimir Guerrero, signed the 17-year-old Kelly in 1982. He was an immediate force on the basepaths and in the field but, initially, struggled at the plate, hitting below the Mendoza line in Rookie ball. By 1987, though, he’d developed some plate discipline and pop, slashing .278/.324/.435 with 13 homers and 51 stolen bases in 118 games at Triple-A. He got the call that year, joining a contending team in a lineup that featured Mattingly, Winfield, Willie Randolph, and Rickey Henderson.

The opportunities were limited at first, with Kelly appearing in just 61 games at the big-league level in his first two seasons. When Claudell Washington departed after the ‘88 season, Kelly took his place in center field. He was expected to play good defense and add an element of speed on the bases. What no one expected was that he would hit better with the Yankees than he had in the minors. Kelly hit above .300 in his first full season, flirting with a batting title in the early going and finding himself in the center of a mini-controversy when manager Dallas Green insisted on keeping him in the nine-hole despite his success.

Kelly’s 1990 season ended up grading out as the best of his career by WAR, largely on the strength of his speed and defense as well as the volume accrued by appearing in every game.

“I rely on my speed and instincts to get to balls that other outfielders can’t reach,” Kelly said of his defensive philosophy. “I play shallow in center field because I want to take away hits from batters and, to me, that’s rewarding. I take as much pride in making a great defensive play to save a game as I do in getting two or three hits in a game.” At the age of 25, he’d established himself as a major-league starter. “I proved I can play at the major league level,” he said after the season. “I’m not going to say I’m the best center fielder, but I’m up there. I still have some work to do.”

That “work” likely referred to strikeouts, as Kelly was punched out 148 times, sixth in the league. Kelly cut his strikeouts nearly in half in 1991 while hitting a career-high 20 homers. In ‘92, after a hot start, he made his first All-Star appearance. “I could sit here and say a lot of people think I’m going to be a superstar,” he said matter-of-factly after his selection. “But I’ve got to drive in runs. I’ve got to put it in writing. That is the only way I will be put in a group with the big guys.” Later that year, though, the Yankees called up Williams to replace Kelly in center, bouncing him to left, in what was likely the beginning of the end of his Yankees tenure. “I’m not going to talk about it now,” Kelly said when asked about the move. “It makes no sense to talk abut something that might get me upset.”

After the season, Gene Michael made one of the most consequential moves of his tenure at GM, trading Kelly to the Reds for Paul O’Neill. Michael called the decision to move on from the talented Kelly “gambling,” chalking it up to a desire to get more left-handed. The trade looked like a win-win in year one, with Kelly making his second consecutive All-Star team while hitting .319. But his season ended in early July due to injury and he found himself back on the trade block the following year, this time heading to Atlanta.

Thus began the former phenom’s second life as a journeyman. Between 1994-2000, Kelly played for eight teams, bringing value as a versatile outfielder and capable big-league hitter. His best season during this period came in 1998, when he hit .323 with 16 home runs in 75 games with the Rangers. Kelly returned home in 2000, signing a minor-league deal with the Yankees before the season and appearing in 10 games before hanging up his cleats at the age of 35.

After his career, Kelly went into coaching, serving as a base coach on the Giants’ 2010, 2012, and 2014 championship squads. He’s currently the manager of the Toros de Tijuana of the Mexican League, a team that won the league’s 2026 championship with help from former big leaguers Justin Turner, Wilmer Flores, and Luis Guillorme.

While Roberto Kelly never experienced playoff glory with the Yankees, his rise signaled a new era of homegrown talent to come, paving the way for the likes of Bernie Williams. More importantly, his talent convinced the Reds to part with Paul O’Neill, whose importance to the ‘90s Yankees goes without saying. Please join us in wishing a happy 62nd birthday to Roberto Kelly.

See more of the “Yankees Birthday of the Day” series here.

The Jays signed Kazuma Okamoto to a four-year, $60 million contract. He had played 11 seasons in the Nippon Professional Baseball League. He hit .322/.411/.581 with 15 home runs in 77 game there in 2025 and .280/.362/.505 with 27 home runs in 143 games in 2024. He had 248 career home runs.

There were questions about his defense at third base, but most thought he would be able to hit. Steamer figured him to hit .251/.323/.446 with 22 home runs in 130 games. I guessed a .250 ish average with 25 home runs and a .340 ish OBP.

Earlier this week, we did a couple of World Series polls — specifically, who would advance to the World Series from the American League and from the National League.

After last night’s game, almost 25% of you are already wrong in regards to your American League picks, as Houston received 11.9% of the vote, and Boston got 11.3% of the vote. Both teams got swept in the Wild Card round.

The top two vote getters, Tampa and Cleveland, are still around, and are, not coincidentally, the two American League teams that received byes. Tampa got 40.4% of the vote, while Cleveland got 25.2% of the vote. The Yankees, who bounced the Red Sox, were the pick of 9.3% of voters, while the ChiSox got just 2% of the vote.

In the National League, the Brewers got a majority of the vote, with 59.8%. The Dodgers were the best of the rest, at 17.1%. The Phillies, who stayed alive with their late comeback last night, were the pick of 8.5% of voters, followed by the Cubs, Padres and Braves at 6.1%, 4.9% and 3.7%, respectively.

As this is written—just before nine o’clock on Wednesday night— it is not yet clear who will start for the Phillies in the deciding game of their Wild Card series. The information is being held, kept close to the vest, perhaps not actually decided. Maybe they’ll sleep on it. Still, one thing is certain: Aaron Nola is going to pitch. Perhaps as the starter, perhaps in relief. But he will pitch. (UPDATE: he will start)

Despite a very solid second half of the season for Nola (3.33 ERA), this fact may prompt some consternation among the fanbase. He is not long separated from a stretch in which he was utterly out of sorts. Even in this late-season surge, he’s been tremendously homer-prone. In the postseason, when a single moonshot can spell the end of everything, it is entirely reasonable to be nervous about his presence. That being said: Aaron Nola is the perfect man for this moment.

Not necessarily in terms of how he will perform. Not being psychic, and being skeptical of fortune telling, crystal balls, horoscopes, and the reading of tea leaves, I do not propose to predict how his performance will go. But symbolically, nobody is more suited to this moment. Bryce Harper is the team’s biggest star, the one most associated with the city the team represents. Zack Wheeler and Cristopher Sánchez are the aces. But nobody, I would argue, represents the Phillies, and these Phillies in particular, than Nola. Being the longest-tenured member of this team, his career overlapping, if only just, with the Phillies’ tenures of Utley and Howard and Hamels, he is a bridge between eras. He was present when this era began, whether you wish to date it back to the signing of Bryce Harper, the 2022 pennant, or the finalization of this current core with Trea Turner’s arrival. If this era should end, with the Phillies being sent ungently into a less-than-good-night, it is fitting that Nola should be present for the curtain’s fall as he was for the rise. If it should continue, with the Phillies raging against the light, and against the hated Braves, it is fitting that Nola should be there as the trail goes on.

But it is not merely his seniority that makes him the most fitting representative of these 2026 Phillies. This year’s Phillies team has been erratic, up and down, magnificent and maddening. Capable in a short period of time of looking unbeatable and looking utterly vincible. And so, too, is Nola. At his best he pitches like a star, dicing and darting with his dervish of a knuckle curve. And his worst, he looks utterly lost, bereft and baffled. The same is true of his team. If the Phillies hack Atlanta’s chophouse to bits with a parade of homers today, it will not surprise. If the bats fall silent, it will not be a surprise. If Nola should demolish the Braves hitters (with, yes, perhaps a solo shot scattered in there somewhere), it will not be a surprise, and if his pitches should be tossed and batted around like a cat’s favorite toy, it will not be a surprise.

Bryce Harper is the icon of the Phillies, the poster boy. He, too, is Philadelphia. But his lows, while attention-grabbing, are not low enough to truly capture the up and down nature of this team, the essence of erraticism that suffuses it, makes their down periods feel endless and the best stretches feel eternal. Yes, he is not always elite. But he has never truly had the variance that Nola does. In Nola’s stretches of brilliance, in his periods of maddening struggle, he is the truest avatar for this team. He is not the anointed hero, and he is not the everyman, he is both and he is in between and he is neither. He is the potential for brilliant leaps and terrible faceplants. He is the embodiment of these Phillies. And no matter what he does in game three, it will be fitting.

And just like that, the season comes to an end with barely a whimper. Over two days, the Cubs looked completely and totally over matched. If you’re a decades long Cubs fan, you’ve seen this before. There were exceptions along the way in the playoff era, but generally the Cubs have a really good season, then get trashed in the playoffs. Here’s the thing though. The Red Sox? Got trashed. The Astros? Showed some fight against the White Sox, but got trashed. By the White Sox of all teams. But then, the Astros were an 81-win team winning a division and reaching the playoffs. I only half jokingly feel like if you can’t win a majority of your games that they should replace your division with another Wild Card for the playoffs. Of course, interleague play was so lopsided this year that you’d only be sliding in another team that barely had a winning record.

So it happens. The playoffs can take a hypothetical two to five percent difference between two teams and make it look like one of the teams is scrimmaging against its Triple-A affiliate. I’ve no doubt that if the Cubs had ever found their footing in this series that it could have looked very different. But the moment can swallow you when it goes bad. The team finishes the season with 53 regular season games and two playoff games since they last won a game where they didn’t homer. That’s a mighty long stretch.

From where I sit, there are exactly three ways to break down methods of winning. First, you can hit a lot of home runs. Second, you can have a really good pitching staff. Keep the score low and you don’t need to score as many runs. This is aided by having a really good defense to make your pitching even better. Third, you can find other ways to manufacture runs. Taking walks, aggressive baserunning and situational hitting.

Hit a lot of homers. Check. This Cub team was built to do that. They spent nearly the entire year at or near the top of the home run leaders as a team. What do I think their long term prospects are there? That’s a tricky question. I felt some of their players underachieved here. Most obviously was Michael Busch. So I’d expect a few guys to post higher numbers next year. But can either Pete Crow-Armstrong or Alex Bregman do what they did again next year? Is Seiya Suzuki back? What do you do with your two corner outfield spots and your designated hitter position? All three of those spots are historically slugger spots in MLB. It doesn’t mean they have to be. The Cubs championship team didn’t actually end up getting great power numbers from the corner outfield and, of course, that was pre-NL designated hitter.

Have a really good pitching staff? Well, no. Two games is a very small sample size. And the day two pitchers were a fair bit more effective than the day one pitchers were. Poor Daniel Palencia. I didn’t see where the numbers ended up, but I know well into the season there had been just one homer on a Palencia pitch over 100 miles an hour. So he puts 101 right in the wheelhouse of Gavin Sheets and Sheets might never have squared a pitch better in his whole career. But for that one pitch, Game 2 might have been a really classic game. That cushion made everything easier for the Padres.

If one were to draw conclusions from those two games, they might decide pitching wins playoff games. That might feel like a sweeping generalization from just two games. But boy I’m sure I’m not the only one who’s ever heard a form of it. I always found an irony that from the moment Theo Epstein and crew came to Chicago they began drafting a slugger in the first round every year. And in those days, the picks were near the top of the round. It felt like they were putting together some slow pitch softball team designed to bludgeon their opponents to death. And in the end, that team was propelled by one of the best pitching staffs in the storied history of this organization. It was aided by an excellent defense.

This organization has got to get better on the pitching side of things. I have one theory on top of all of the obvious ones. The obvious ones being find more of those guys that can dial it up into the high 90s and more. Find more of those guys with the stuff that dances all over the place. Ryan Zeferjahn makes us all nervous because it feels like he doesn’t know where the ball is going when he releases it. I don’t know if he’ll ever fully harness his stuff. But I know that Ryan is exactly what the Cubs need more of. A lot more.

My theory? This team started fixating some years ago on strike throwers. It doesn’t like allowing walks. For all of the ire the pitching staff received, they only allowed the 12th most runs among MLB teams. That is actually pretty decent. Of course, they were significantly aided by the best defensive unit since the current defensive metrics were put in place. One reason for that: They were ninth in fewest walks allowed. Two guys who have been susceptible to allowing a ton of homers are Jameson Taillon and Shōta Imanaga. Both work a ton in the zone and neither has particularly elite stuff. I’d argue that in getting allergic to allowing walks, they’ve found guys who are susceptible to homers. Walks are almost always bad. I do like the idea of limiting them. But a bad pitch in the zone will get you killed.

That last point was a nod towards small ball. It’s a lost art. The Cubs do have a lot of team speed. They also had one of the more prolific base stealers in baseball. And yet, they were 10th in steals. They drew a lot of walks. And they probably led the league in singles that advanced all of the runners exactly one base. This team was so good at getting runners on base that they tended to wait around for one big hit. In the regular season, those hits often came. But there were still long stretches where the offense would vanish. This isn’t new, we’ve been saying it since 2017. I don’t watch other teams or deep dive them statistically. I suspect to some degree or another these things happen to all of the teams. So this is probably not something to overthink.

Still, when the margins decrease, being able to actually put down a bunt or hit the ball to the other side. Those are dying arts. I know that is widespread. Chalk that up to one of the negative side effects to numbers crunchers getting heavily involved with the sport. There is value to those soft skills. I will grant that so many pitchers throwing 98 plus really makes that complicated. It was definitely easier when you were seeing a lot of pitches in the 80’s back in the day when starters were throwing every three or four days and throwing regularly into the seventh and eighth innings.

The game evolves. That’s part of what keeps the game interesting. I definitely liked the old game where the starters were of paramount importance and guys who knew how to have productive at bats with runners on were more valuable. But it’s hard not to appreciate teams like the Padres and their next opponent, the Brewers, with all of their pitchers with really elite stuff. The game is changing. Some of the old stuff works. A three-run homer has been effective for all of baseball history and will likely never go out of fashion. But there are other ways for sure.

Happy Wait Til Next Year Day to all who celebrate.

Three Postives:

• David Peterson faced five hitters and recorded five outs. He did allow a hit, but also picked off a runner. I would have probably had him start one of the games. I don’t expect it would have changed much.
• Nico Hoerner had two more hits, one a double. Might want one or two more of these guys who handle velocity well.
• Tyrone Taylor had a hit in his only at bat of the series. I’m not sure he’d have been in the lineup even if Alex Bregman had been able to play the field. It would have been nice to see Taylor and Conforto rather than Pedro Ramirez and Matt Shaw (particularly against right-handed pitching).

Game Two, September 30: Padres 4, Cubs 1 (0-2)

Reminder: Heroes and Goats are determined by WPA scores and are in no way subjective.

THREE HEROES:

• Superhero: Nico Hoerner (.109). 2-4, 2B, RBI
• Hero: Carson Kelly (.068). 1-3, HBP
• Sidekick: David Peterson (.027). 1.2 IP, 5 BF, H, K

THREE GOATS:

• Billy Goat: Dansby Swanson (-.171). 0-3
• Goat: Daniel Palencia (-.113). 1.2 IP, 7 BF, H, R, 2 K
• Kid: Pete Crow-Armstrong (-.104). 0-4

WPA Play of the Game: Gavin Sheets hit a two-run homer in the fourth, effectively ending the series. (.176)

Cubs Play of the Game: Nico Hoerner batted with runners on first and second in the top of the fourth and one out. He singled and a run scored. (.114)

Cubs Player of the Game:

Game 1 Winner: Nico Hoerner received 38 of 67 votes.

Up Next: Nobody really knows. The offseason looms after the rest of the playoffs unfold. I’ll be rooting for the Rays the rest of the way. I’m always going to throw my support behind the teams that excel in scouting and player development. After the playoffs? A work stoppage. The sides seem intent on this being a long one. Everyone is making a ton of money and baseball feels like it has made something of a resurgence in popularity. Definitely time for a work stoppage.

I’ve never been put into the position of a mediator, though I do mediate very regularly. Were I asked to mediate, I would give both sides an opening statement that would say that both of you do put forth some good arguments about why the other side frustrates you and is difficult to deal with. I get why the friction is there. I get where there are goals that are very much in contradiction to one another.

I’d tell them that you should have come to me with a very clear list of things you wanted. Then I’d tell you that you aren’t getting all of them. That’s the way mediation works. Neither side is going to get everything it wants. Ordinarily, you’d say that each side figure out their number one priority and try to satisfy that. I’m afraid that it would generally look like one side wants a much more formalized salary structure and the other wants no part of it. I guess I’d try to come up with some loosely formalized salary structure and a significant increase in the amount of revenue going to the players. You take this thing that you don’t want, but you get what you really want. At the end of the day, the players want an increasingly large amount of money. Shouldn’t we all?

That has to look like teams at the bottom spending (way) more. The players get a larger chunk of the revenues. The players share is absolutely indexed to inflation or a standard increase or whatever, so they don’t have to collectively bargain increases. And the owners get some very basic structure that is a bit more harsh than what exists now. I suspect this is the outcome. Or close to it.

How long will that take? Who knows. Until then, extra time to rest and recharge and remember all of the other things we do for fun. I’ll try to pop in from time to time in the offseason. Until then, thanks for your clicks, your comments and a kind word from time to time. They keep me going when the days seem to stretch without end. I wish all of you well in whatever comes your way.

Maybe next year will be the year, right?

Go Cubs.