Ten seasons. Ten playoff appearances. Not nine. Not eight. A perfect 10-for-10. This is a streak nobody else in this league can match this decade. Not Robby. Not Bobby. Nobody.
And yet… he’s not ranked No. 1 in my decade rankings.
We’ll get to that. But first, let’s revisit one of the most consistently dominant ten-year runs this league has ever seen.
It all started with winning. Lots of winning.
Rich’s first five seasons of the decade were nothing short of spectacular. In 2016, he went 9-4, earned the No. 2 seed, and captured the scoring title. He opened the playoffs by knocking off seven-seeded Eric before defeating five-seeded Bob, then capped it all off with a dominant 1,846-1,180 championship win over top-seeded Jeff to claim his second career title.
The following season wasn’t quite as smooth. Despite finishing just seventh in scoring, Rich still won eight games and secured the No. 3 seed. His season came to a heartbreaking end in the quarterfinals, falling to six-seeded Eric by only 29 points, 1,433-1,404.
Then came 2018—a season that looked dead in the water. Sitting at 4-7 with two weeks remaining, Rich needed to win out and get some help just to have a chance. He did that and got the help, sneaking into the playoffs at 6-7 as the No. 5 seed. Once there, he caught fire, crushing fourth-seeded Masterson 1,757-1,073 before edging sixth-seeded Don 1,682-1,606. The Cinderella run finally ended in the championship game, where he fell to Neatock, 1,631-1,578.
The 2019 and 2020 seasons marked the best back-to-back regular seasons of Rich’s career.
In 2019, he ripped off nine straight wins to open the season, the longest season-opening winning streak in league history, and became just the third manager ever to finish the regular season at 12-1. Like the other two members of that exclusive club (Bob and Robio), he reached the championship game, only to run into what the numbers say was the greatest team in league history: my 2019 juggernaut.
He followed it up with another double-digit win season in 2020, finishing 10-3. Once again, he claimed the No. 1 seed and finished second in scoring. After eliminating eighth-seeded Colby in the quarterfinals, his title hopes were ended by me… again… in a 1,762-1,268 semifinal loss.
Take a second and appreciate what those first five years looked like.
Over that stretch, Rich went 53-24, a remarkable .688 winning percentage. He finished in the top three of both the standings and points in four of those five seasons. He avoided a weekly low score in four of those five years, went 4-1 in the quarterfinals, 3-1 in the semifinals, reached three championship games, and came away with one title.
That’s about as dominant a five-year stretch as we’ve ever seen.
The second half of the decade wasn’t quite as overwhelming, but every single season still ended with a playoff berth.
He finished 7-7 in both 2021 and 2022, followed by an 8-6 campaign in 2023. He entered those postseasons as the No. 5, No. 6, and No. 5 seeds, respectively, but all three runs ended immediately in the quarterfinals.
Then came 2024, when Rich looked like vintage Rich again. He closed the regular season on a six-game winning streak, finished 12-2, earned the No. 1 seed, and once again ranked second in scoring.
Unfortunately, the playoffs had other ideas.
For the fourth consecutive season, his postseason ended after just one game, this time in a 1,635-1,458 upset loss to eighth-seeded Colby.
In 2025, it looked like the playoff streak might finally die. Rich stumbled to a 1-5 start and seemed destined to miss the playoffs for the first time this decade. Instead, he did what Rich always seems to do. He won five of his next six games, clawed his way into the postseason at 6-8, and quietly finished fifth in scoring. As the eighth seed, he was a legitimate threat, but he ran into another buzzsaw. Despite posting an impressive 1,716 points, he lost to top-seeded Robio, who exploded for 1,980.
Looking at the decade as a whole, the résumé is incredible.
Rich’s 94-59 record (.614) is the best of the decade. He averaged 1,437 points per game; just one point behind me for the highest average. His average finish in the standings (3.70) and points (4.20) are both the best in the league. He topped 1,500 points in 61 of his 153 games (39.9%), second-best overall. He posted 18 weekly high scores (second most) while suffering only seven weekly low scores (third fewest), giving him a league-best +11 differential.
So how does someone with numbers like that not finish No. 1?
First, despite making the playoffs all ten years, Rich is just 9-9 in postseason games, ranking sixth in playoff winning percentage. After a third title game appearance in 2019, he’s just 2-6 in the playoffs and he hasn’t won a single playoff game over the last four seasons. As the top-seed three times, he’s just 3-3 in the postseason.
Still, context matters.
In the nine playoff games that ended Rich’s seasons, his opponents averaged an astonishing 1,692 points. Seven scored over 1,600, and three topped 1,900, proving that sometimes you don’t get beat; you just happen to be standing in front of someone having the best week of their life.
In the end, though, the deciding factor came down to one matchup. The battle for the top spot came down to Calderon and me, but in head-to-head meetings, it hasn’t been much of a battle.
Over the last decade, Rich is just 4-10 against me, including 0-3 in the postseason.
When you’re trying to separate two all-time great résumés, those head-to-head battles become impossible to ignore.
So Rich finishes No. 2.
It feels strange to say that about someone with the decade’s best record, ten straight playoff appearances, and a trophy case with a few deep postseason runs and one championship. But that’s how absurdly close the race was.
If there’s one sentence that sums up Rich’s decade, it’s this: nobody was more consistently excellent… he just kept running into someone else’s career week or, unfortunately for him, into me.
Ten straight playoff appearances is an incredible legacy. No amount of defeats will take that away from him.