Seven games into the 1989 campaign, tight end Chris Dressel was with his fourth team in seven seasons, and knew how things worked in the NFL. Not on game days when thousands of fans are watching from the stands or on TV, but behind the scenes.
"I was playing with Kansas City and Marty Schottenheimer was our coach, and he was all up in arms about our special teams. He was putting starters on the kickoff team, and there was one guy coming off of I.R., and I was like, 'I wonder who the odd man out is? With somebody coming off, somebody's got to go,'" Dressel said.
"And so we practiced through the week and I didn't really think anything of it. And then on Friday, we were doing field goals, and the special teams coach said, 'Hey, Smith, get in there for Dressel.' And I was like, 'I'm the odd man out.'
"Practice is over and I'd played for Marty in Cleveland for a couple years, so Marty and I had a really good relationship. He saw me waiting for him, and before he could say anything, I started swearing at him. 'Put me on the kickoff team. Why am I losing my job?'"
Dressel continued. "He said, 'We'll waive you and bring you back on Sunday.' So we go to Pittsburgh to play the game and on the plane he sat next to me and said, 'Yeah, my plan didn't work out so well. You're the starting tight end for the New York Jets. Their tight end got hurt and they don't have anybody on their roster.'
"And so I went from not being wanted on Wednesday to being a starter on another team. Losing my job in K.C., I was not pleased, but didn't realize that it would turn out as well as it did."
Joining the Jets in midseason, they finished with a 4-12 record and watched head coach Joe Walton be replaced by Cincinnati's offensive coordinator Bruce Coslet, who, as a tight end himself, had played eight seasons for the Bengals.
"My early indicators were that they wanted me back. I kind of landed in a good spot," Dressel said. "I was happy to be in New York. I'd bounced around and having a team that wanted me was great at that point in my career.
"It was a really classy organization. All of the people that worked there, and I'm not just saying the coaches. I'm thinking administration, ownership, just the way they treated the players was absolutely notable for me just based on the fact that I had plenty to compare it to."
While feeling wanted may have been great, being in New York offered another benefit for Dressel off the field, as well. A benefit best experienced wearing a tie dye T-shirt.
"The greatest thing for me when I was in New York was being comfortable with where I was, what I was doing. And it's not football related, but I'm a Grateful Dead fan," Dressel said. "And one of the highlights was that the Grateful Dead would come to Madison Square Garden in October and play nine shows. It would be three shows, a day off, and then three shows, a day off, and then three shows. And I would typically get to seven out of those nine shows. The two that I didn't get to were the two that were the night before the game or if we were traveling."
Even before he was drafted by Houston out of Stanford University in 1983 and spent nine seasons in the NFL with five different teams: the then-Oilers, 49ers, Browns, Chiefs, and Jets – Dressel had launched into a post-playing career.
"I was super fortunate. My uncle, Russ Flynn, who was living and working in San Francisco, followed my career at Stanford," Dressel said. "My senior year, I hadn't been drafted yet, but knew I was going to get drafted and get a bonus. So Russ actually co-signed on a $50,000 loan, and I invested in a building in San Francisco. And then when I did get drafted and signed my contract, I paid off that loan."
Dressel would join his uncle in Flint Investments, a company which operates residential and rental properties in San Francisco proper.
"Through the years I was playing, I was investing pretty much as a silent partner. But I was following his tutelage and it was super important because it's a tough haul for guys (after playing) in the NFL to make it work," Dressel said. "It's kind of a broken record. Guys only play three or four years, and if you spend like you're going to make that kind of money for the rest of your life, you're not going to have any left at the end. I was pretty fortunate to have somebody show me the way.
"Unfortunately, Russ passed away right before COVID started. But he and I were partners for almost 39 years. And now my cousin, Sara, and I have been working side-by-side. My work has a ton of variety. I work with brokers. I work with bankers. I work with realtors. I work with vendors. I work with managers. I work with a ton of different groups of people."
Dressel, who lives in the Bay area and has four daughters: Julia, Morgan, Dea, and Flynn, continued. "We have a lot of ground floors, mom and pop leasing. I don't do any of the day-to-day stuff. I've got a handyman who deals with the leaky toilets and all that stuff. I can't do that anymore. But I do all the other stuff."