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As the Fantasy Baseball season rolls on and players have arrived in their new destinations after the trade deadline, now is the best time to reflect on the season. More specifically, we'll look back today on our biggest regrets, victories, strategies we've applied that have worked and others we plan to roll with moving forward.

To kick off each week of the season, I'll be reaching out to Fantasy Baseball Today's Chris Towers, Scott White and Frank Stampfl to ask them a few big questions that can hopefully help lead to actionable advice. With Frank on vacation this week, it will just be Scott and Chris delivering the good. If you are reading this and have specific questions you'd love to see Chris, Scott and Frank answer, please DM me @DanSchneierNFL. And remember that if you don't like any of the answers, I'm just the messenger, and you know what they say about the messenger.

  1. What is your biggest regret from the 2021 season so far?

  • Scott: My biggest regret is not being selective enough with my starting pitcher picks. I wanted a big stable of potential high-end hurlers, mostly to account for the high failure rate at the position, so I broadened my definition to include guys like Kenta Maeda, Dylan Bundy and Zach Plesac whose reputation was mostly built on the bite-sized 2020 season. Maeda is finally coming around, but it's too little, too late. Questionable picks like those would have been better spent on hitters, who it turns out weren't as plentiful on the waiver wire this year as in the previous two.
  • Chris: It's probably how skeptical I was about Matt Olson. I have a tendency to write players off as finished productions, but the growth he has shown, especially in his contact rate, is a helpful reminder that players are constantly evolving. He went from one of many one-dimensional power hitters to performing like one of the best hitters in baseball. If he can close out the season with his strikeout rate under the 20% range, he might need to be a top-40 pick next season. 

2. What's your biggest accomplishment?

  • Scott: I think it's how I identified some of this year's biggest breakout players just by observing them in spring training. That's a dangerous game to play, and so it's easy to shy away from it. In the case of pitchers Carlos Rodon, Trevor Rogers and Freddy Peralta, though, the cost never became unreasonable, making the gamble easy to justify. Even Shohei Ohtani, with all the hype he was getting in March, continued to last beyond the top 130 picks, which seemed like easy money to me. Looks like Akil Baddoo and Logan Webb are finally coming around, too.
  • Chris: I had great success identifying sleeper pitchers who worked out for me. Scott and I had a lot of back-and-forths about the right way to value pitchers, and I generally valued them less. However, identifying the likes of Pablo Lopez, Trevor Rogers, Freddy Peralta, and more has helped keep me afloat while my early-round hitters have been inconsistent. 

3. What strategy have you added to your game that has worked?

  • Scott: The Head-to-Head categories format hasn't been my best in recent years, so I approached it differently this year. I loaded up on pitching early, like I'd do in a points league, figuring those categories would be the most difficult to repair off the waiver wire. But when the time came to draft hitters, instead of looking to balance the categories like I'd do in Roto, I went for power, power and more power. Any home run hitter can get hot enough to carry a team in four of the five hitter categories in a given week, and they don't all have to be hot at once. Anyway, it's worked, because I'm in first place.
  • Chris: Coming into the season, I looked back at historic ADP data to try to figure out what the best approach for acquiring pitching was, and the results were pretty clear: You want to invest in aces or you want to invest very little. That strategy has worked out really well this season, with the top-12 pitchers generally living up to expectations while the No. 2 and 3 range has been pretty terrible. 

4. What strategy have you debuted that has not worked and why?

  • Scott: Mainly, it's the Rotisserie leagues where going all in for starting pitching -- as in three of my first five picks and five of my first 10 -- has backfired, which I suspect is because of the volume of hitters that's required in that format. Typically, you're starting an extra corner infielder, an extra middle infielder and two extra outfielders as compared to a Head-to-Head league, which makes for too many lineup spots to patch up on the fly, particularly with the change in offensive environment this year.
  • Chris: It's hard to come up with a good answer for this, but my decision to bet on injury-prone players like Byron Buxton and Giancarlo Stanton has kind of blown up in my face, though I'm not sure there's necessarily a lesson here. Sure, Buxton has struggled to stay healthy again, but his most serious injury came when he got hit by a pitch. Stanton, meanwhile, has mostly stayed healthy finally, but hasn't been the same kind of hitter we expected. It's a risky strategy that hasn't really paid off for me, but I'll still be willing to buy discounts where they appear. 

5. What is the biggest change you project for the Fantasy landscape over the final months?

  • Scott: I've said it before, but I think teams will redouble their efforts to preserve pitchers' innings down the stretch. This goes for contenders and non-contenders alike. We're already seeing it from teams like the Brewers and Tigers. The curtailing will mostly take the form of shorter outings, maybe with two starting pitchers working in tandem, and it'll mostly afflict younger pitchers. It'll lead to some of us having to roll the dice on relative no-names, especially in deeper leagues. Who knows? Maybe my all-in-on-pitching strategy will get the last laugh after all.
  • Chris: It's hard to have any predictions in a season as unpredictable as this one, but I'll offer one: The mostly disappointing rookie class will start to make its presence felt. Rookies collectively have struggled, putting up the worst performance of the last 20 years, but Wander Franco is turning things around, Jarred Kelenic is showing signs of life, and Jo Adell has the kind of skill set that could help you win a championship over the final two months.