The 2026 Oakland Roots End-of-Season Awards: Mad Men Style, Part I

Last year, I was lucky enough to become a father for the first time.

In the midst of changing diapers, feeding, burping and putting my baby boy to sleep, the sheer amount of time spent sitting in those first few weeks caught me completely off guard.

I sat feeding him. I sat while soothing him. I sat when we had skin-to-skin time. So much sitting.

I spent so many hours in our living room rocking chair with my son. Often, I was so exhausted I’d just sit there holding him while he slept. To stay awake, I’d turn on the TV. I needed something light that wouldn’t demand much brainpower, something familiar.

One day, I accidentally stumbled on a channel running a Mad Men marathon that looped for a month. I watched an episode and was hooked.

Mad Men is my favorite show. I started watching it in college, right before Season 5 premiered, as I caught up on all the shows from the Golden Era of Television.

I was 20. I was young. Naive. I took all the wrong lessons from the show. I thought Don Draper was a bad ass (and honestly, part of me still does).

That’s the great thing about books, shows, and movies though. You can revisit them at different points of your life and walk away with completely different lessons.

They don’t change, you do.

When the marathon ended, I started a complete rewatch in order. And then I got the idea for this article.

Another favorite of mine? Bill Simmons.

In high school, my family didn’t have a computer for the longest time. I had a Computer Lab class in high school and the teacher would give us the first ten minutes of class to do silent sustained reading on the computers. That’s when I discovered Simmons.

Growing up, I read  the sports section of the newspaper religiously. My grandpa would grab the newspaper after our neighbor was done with it to check the results from Golden Gate Fields. When he finished, I would take it and read about the Raiders, the A’s, and the Warriors.

Simmons blew my mind. He wrote unlike anyone I’d read in the newspaper. The informality of the writing, the humor, the pop-culture references. He instantly became my favorite writer.

One of my favorite Simmons’ gimmicks? “The Movie Quotes / NBA Awards” article. Instead of handing out traditional awards, Simmons would choose a movie, pick quotes, and assign them to players, moments, or coaches from the NBA Season.

So in honor of my son and my favorite writer, here are the end-of-season Oakland Roots awards, Mad Men style.

The Let’s Take It Slow Award

Quote:

“ ‘A man like you, I’d follow into combat blindfolded. And I wouldn’t be the first, am I right buddy?’

‘Let’s take it a little slower, I don’t want to wake up pregnant’” – Pete Campbell and Don Draper

Winner: The Blog After Tucker Lepley’s Debut

Expectations were high following the acquisition of Tucker Lepley on loan from the LA Galaxy in May. It was the first time the Roots brought a player on loan since Ottar Magnus Karlsson and Mikael Johnson in 2022. For the Roots to break tradition for Lepley, they clearly saw something they liked.

Lepley somehow exceeded those expectations in his debut, a 2-1 victory against El Paso in May. In 35 minutes, he took 32 touches, completed 25/26 passes, and, most importantly, curled a shot into the back of the net to give the Roots the lead in the 83rd minute.

The excitement was immediate. Our blog predicted that he should be “a menace at the USL level” and that he “provides the Roots with an X-Factor,” while Martin said Lepley would “feature heavily” because of his ability to play anywhere in the midfield. He also called Lepley the kind of player who was “hard to find in this league.”

It looked like the Roots had struck gold.

Then it kind of fizzled out.

Lepley struggled to gain a steady, significant role on the team. He started only four matches. In the final seven matches of the season, he only made five appearances for a total of 29 minutes.

Lepley never became the central figure many expected after his dazzling debut. That’s okay. Most loans don’t work out. Not every promising start turns into a breakthrough season. Roots fans are awfully familiar with that fact.

In hindsight, we may have gotten a little ahead of ourselves. After all, the award wasn’t awarded to Lepley. It was given to us.

The Selective Amnesia Award

Credit: Oakland Roots SC

Quote:

“Get out of here and move forward. This never happened. It will shock you how much it never happened” – Don Draper

Winner: Jesus de Vicente

Jesus de Vicente had the inverse experience of Lepley.  He made his Roots’ debut during the March draw against Phoenix due to a rash of injuries at the fullback position. It was a debut to forget.

In twelve minutes, the Spaniard was dispossessed, dribbled past twice, lost four of five ground duels, committed a foul, and provided the space to Charlie Dennis that allowed Dennis to deliver the assist on Phoenix’s equalizing goal.

After the match, I wrote that, “de Vicente’s performance puts Martin at a crossroads.” He could either bench de Vicente or play the long game and develop de Vicente, trusting that  the, “patience may pay off later in the season.”

Boy, did it.

After the Phoenix match, de Vicente took Don Draper’s advice. His six assists only trailed Wolfgang Prentice’s seven on the team. He actually bested Prentice in big chances created, 13-10. No one came closer to de Vicente’s 45 chances created. The second-place finisher Florian Valot (31) was as close to fifth place as he was to de Vicente. The fullback was the Roots’ best offseason signing and has a strong case as the team’s MVP.

His performance was not only impressive on the squad level, it was impressive on the league-wide level. On a per 90-basis, his assists ranked in the top seven percent at his position. His chances created, big chances created, and successful crosses all ranked in the top three percent at his position. His play earned him an Honorable Mention selection on John Morrissey’s USL Tactics Championship Best XI lineup.

It’s hard to imagine a bigger reversal this year. Twelve minutes into his Roots career, de Vicente looked like a player who would fight for minutes. At the end of the season, he looked indispensable.

The Let’s Lower the Bar Award

Credit: Oakland Roots SC

Quote:

“You do not cover for me – you manage people’s expectations” – Don Draper

Winner: Ryan Martin

After the home draw to Monterey Bay in August that severely damaged the Roots’ playoff chances, Ryan Martin stated, “Our next focus is San Antonio and not necessarily the playoffs. Obviously, we want to be in the playoffs, but it takes time… It takes time to build.”

While I understand the sentiment, the comment struck me as odd.

To be fair, Martin and the team never quit. They took it down to the wire at Sacramento. They gave the fans, especially those in Sacramento, some moments that they will never forget.

Still the comment lingered with me.

It’s true that building a culture takes time. Developing a system takes time. Competing for championships takes time.

But in the USL, where two-thirds of teams make the postseason, making the playoffs should not take time. It definitely shouldn’t take two seasons.

I don’t expect a team to promise a championship. I understand that building a competitive team takes time. I watched the Warriors toil for decades before breaking through. But there’s a difference between acknowledging that the process takes time and lowering the expectations for what that process should accomplish.

If making the playoffs was a goal, I wanted Martin to communicate that. I wanted to hear about competing, not patience. And if the playoffs weren’t a priority, that should have been communicated before the season started. Preferably before supporters like myself bought season tickets and bought into the most dangerous thing of all: hope. And certainly not in late August, after a terrible stretch, when the playoff hops were already on life support.

Check back next week for Part II!


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