Since the Last Time the Yankees Made it to the World Series…(2024)

Originally published

A lot of my friends would describe me as a die hard Yankee fan. I try to watch every single pitch of the 162 game season, and I live for the playoffs.

Growing up in the 1990s, I got spoiled. They won the World Series 4 times during my most formative years.

It’s been 15 years since the Yankees made it the World Series — and a lot has happened. I:

  • Started a left the 2 jobs I had where I wasn’t self-employed
  • Met, started dating, and married Erin (Erin was floored that the Yankees have never made it to the WS since we met each other)
  • Moved 5 times
  • Bought our first house
  • Had 3 kids
  • Started all of my podcasts
  • Stopped doing web development and coach people now
  • Watched the Giants win their most recent Super Bowl
  • Ran* 2 half marathons and a 10K
  • Wrote 5 books
  • Started smoking cigars

…and my parents sold our childhood home. Before the World Series start, my brothers and I are helping them move out, and into their new house in upstate NY.

I try to be honest with myself in these posts — and if I’m being honest, it’s been a tough couple of months.

One of the reasons I love baseball is that it’s an escape. And while I don’t think anyone who’s seen my watch baseball would say it relaxes me, it’s something I can really get into for 3-4 hours.

I’m so excited to see this team in the World Series. Whether it’s against the Mets, in Subway Series 2.0**, or the Dodgers, whom they’ve seen 11 times in the World Series but not since 1981*** — I can’t wait for some incredible, late October baseball.

*Ran is generous. I participated in and completed 2 half marathons and a 10K
**The Yankees won the last time, in 2000.
***They lost that one, and it started the last 15 year WS drought