How To Win Ottoneu: An Interview with Josh Jessar

There’s somewhat of a tradition to interview the annual winner of the Ottoneu Champions league.  This year I have the honor of picking the brain of the first ever repeat winner, Josh Jessar, who also happens to be the first back to back champion of the league.  You can see a full breakdown of his winning roster here.

Q: How long have you been playing fantasy baseball? Ottoneu?

I’ve been playing fantasy sports since the late 80’s, starting with football teams based on Christian Okoye and Barry Word.  I became the only east coast Chiefs fan I knew. Baseball followed shortly after. My collection of friends have played on and off ever since across a variety of platforms.  I started playing Ottoneu in 2013. Longtime readers of your work may remember an interview with previous Champs winner Keith Smith…I recruited him to join the Ottoneu movement.  It was a natural extension of our after school sessions from back in the day.

Q: How did you stumble upon Ottoneu?

Another longtime friend from back in those early leagues brought me to it.  We’d actually kicked around the idea of starting our own fantasy site complete with termed-contract players in the early 2000s.  When he told me of this great site he’d discovered with a lot of the same concepts, we decided to try it out and were both hooked immediately.  He’s a great player who was in Champs B for a while, but after his fourth kid arrived he went into retirement. I’m hopeful he’ll one day make a triumphant return.

Q: You are the first repeat winner of the Champions League, and now have back to back titles.  What is your secret sauce?

I’m good at quickly understanding the current state of any given league and managing resources given that context.  Like a lot of Ottoneu players, I generally take a stats-heavy approach. That used to mean making my own player databases and models, but at this point I’ve internalized a lot of that and tend to use stat shortcuts that correlate well with results for player evaluation, such as max exit velocity for hitters and K-BB% for pitchers.  Now instead I spend more time studying positional strengths and weaknesses across the league as well as opponent strategy. Many of my moves reflect both what I think is best for my team and what will do the most to limit options for my top competitors.

Q: You won the 2019 season by less than 150 total points (essentially one good day’s worth of production).  What was it like competing in a photo finish up to the last day of the season?

It’s great, win or lose.  Fantasy points leagues are typically over much sooner which leads to a bit of a slog come mid-August, but I’ve been lucky enough to find myself in tight leagues a few times in Ottoneu.   It helps the summer fly by and while it can be a little stressful it also helps me improve my focus for even early decisions in following years.

Q: If you had to boil your season down to just one decision you did or did not make that made all the difference, what would it be?

It didn’t work out very well for me as the guys I got back uniformly stunk up the joint, but my decision to trade Luis Severino after his injury for Nathan Eovaldi, Jose Martinez, Alex Reyes, and Michael Kopech set the tone for what would be a season-long theme.  This season it greatly benefitted me to move on quickly from hindered pitchers and free up resources to chase new ones…Severino, Kluber, Carrasco, Folty, Montas, etc. Had I tried to weather the storm and keep those guys, I’d have been pushing relegation.

Q: You picked up some great players throughout the season (deGrom, Cruz, LeMahieu, Hoskins).  What is your general approach to trading, and your view of how your trade tactics should be adjusted during a very tight race?

My approach to trading changes quite a bit with timing and competitive positioning.  In the offseason, I’m usually trying to accomplish two goals…get the best top-end talent I can or cut salary by trading good but relatively expensive players for assets I expect to accumulate value in the near-term based on a new opportunity, return to health, or a skills improvement.  During the season, I’m usually trying to trade away players with increased perceived value to improve my near-term situation, but that can take a lot of forms. Early this year, I traded Mitch Keller and Austin Riley for a couple of expensive relievers solely so I could get a loan and cut them to build cap room, since the league funds had mostly been spent and I wanted to play the wire.  After a hot April for him but a cold one for my team, I traded Paul DeJong and Christin Stewart for a slow-starting Jacob deGrom, which was an absolute steal that restored any chance I had to compete. I think I was only able to pull that off because my team had been so bad to that point that the player selling deGrom didn’t think I could win.

Q: You built your team around some great players this season, but which under the radar player felt like such an integral part of your team that you couldn’t do without them?

Jorge Polanco was my biggest offseason pickup and steady for most of the year out of my MI spot.  You mentioned Rhys Hoskins as a trade acquisition, but he was horrible for me and I’d have been ashamed if he’d been the only return I got for Luis Robert.  However, I made sure to get JD Davis back in that deal and he was huge down the stretch. Last but not least, Brian Anderson put up over 7 PPG for me. Both he and JD were cheap guys I’d wanted for a while as their expected stats were clearly better than their actuals.

Q: What advice do you have for Ottoneu owners who find themselves in a tight race?

Don’t be afraid to burn a lot of future value.  In my experience it is far easier to pare down an expensive roster in the offseason than most people realize and there are always new prospects coming available.  Also don’t be afraid to cut expensive players at the end of the season if you need money for defensive bids. Odds are you’ll need to cut anyway in the offseason to get back under the cap limits in any event.

Q: The Ottoneu Champions league includes a relegation clause that automatically ejects the last two owners in the standings each season.  How has this form of relegation added or subtracted from your Ottoneu experience compared to other leagues you’ve played in?

It has extended the window before teams feel able to sell in earnest for the next season, which has in turn extended the competitive window and allowed for closer races at both ends of the standings.  This is a fantastic outcome that leads to an engrossing experience across the league. Relegation has also led to a little less prospect hoarding, which I think is good because it is just bad strategy for more than a couple players in A ball to be held anywhere throughout a league.

Q: What is your opinion of the current home run spike in baseball and the impact on fantasy baseball? You led the league in P/IP – what was your approach to pitching in this environment?

I hate the home run spike as a baseball purist.  As a fantasy player, I think it has done a couple distinct things.  The infield now has too many great players since so many former contact hitters are now smashing bombs, while the OF still has too few.  A team with a few elite OFs and some guys to platoon through the rest of the OF spots will be able to stumble upon good offensive infielders almost by accident.

As for pitching, while the rest of the league mostly shrank away from paying for pitching at all, I wanted to collect as many elite guys as I could.  I just didn’t trust anyone else and was willing to overpay for confidence. This introduces a lot of volatility due to injury risk (which I certainly experienced), but I think it can be managed given the democratization of offensive talent beyond OF.

Q: Name one hitter and one pitcher you have your eye on as breakout players in 2020?

Given playing time and the continuation of a juiced ball, I like Josh VanMeter’s plate approach and home park.  I think he’ll return nice mixed-league value as a utility guy.

Jesus Luzardo will stay healthy and be a beast.  He’s filthy.

Q: Who will win the World Series and WS MVP?

Houston just put up the second-best wRC+ offensive season in history, has the two best SPs in baseball, recent championship experience, and basically no weaknesses.  So I’ll say the Yankees to be contrary, with preseason afterthought DJ LeMahieu garnering MVP honors.