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MLB Playoffs: A Free Agent Feeding Frenzy

Last Updated: October 5, 2023
The Boardroom Hardball Roundtable convenes on the first day of the postseason to discuss everything from the MLB Playoff format to the free agents with the most to gain.

Well, beat the drum and hold the phone, the sun came out today. It’s October, and there’s postseason branding on the field.

That’s right, the MLB Playoffs are here, and thanks to baseball’s new postseason format, we dive right into it with back-to-back quadruple-headers on Tuesday and Wednesday this week as eight teams battle for the right to play in the division series.

This year, the playoff bracket might look a little different, with big-market October mainstays New York (both teams) and Boston completely absent from this year’s proceedings. But make no mistake: there are storylines abound. And so, as is only right, we gathered Boardroom’s Baseball Luminaries at the proverbial Hardball Roundtable to talk through some of them, from free agent implications to bigger-picture MLB playoff format proposals.

Here’s what we tackle:

  1. Which upcoming free agent(s) have the most to gain or lose during the playoffs?
  2. How would you improve the format of the MLB Playoffs?
  3. Which team(s) would benefit most from the postseason format?
  4. Fearless prediction! Who is your World Series champion?
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Which upcoming free agent(s) have the most to gain or lose during the playoffs?

Griffin Adams: I’m not sure if this is a personal thing, but I’ve always felt pitchers heading for free agency carry way more pressure than their counterparts. Therefore, I will go with Phillies ace Aaron Nola on this one.

Philadelphia has seen the good and the bad with Nola. It started with his strong showings through the Wild Card and Divisional rounds last postseason, earnings victories by going six-plus innings in both. Then, he followed that up with three winless starts in the NLCS and World Series. The Phillies reportedly offered him upwards of $100 million and Nola declined, so it seems he’s ready to test the market. How he performs this postseason will affect how negotiations go down this offseason.

Sam Dunn: I was tempted to say Padres ace Blake Snell, but then I remembered that San Diego blew it and missed the postseason entirely. How on earth did they (and their payroll) manage that, exactly? Well, my next thought was Cody Bellinger, but my actual pick is Matt Chapman.

Toronto’s man at the hot corner experienced a down year offensively, but he’s hitting the market for the first time at the age of 30, and his defense remains elite-tier. He could easily earn a deal in the Alex Bregman/Jose Ramirez zone between $100 million and $150 million in total value. If he goes on a tear, he could make that sort of money in three to five years rather than Ramirez’s seven.

Shlomo Sprung: Texas starter Jordan Montgomery has been excellent since the Rangers acquired him at the trade deadline, with a 2.79 ERA in 11 starts in a ballpark that leans toward hitters. While Philadelphia’s Aaron Nola is going to get paid regardless of how he fares in the postseason, a truly dominant playoffs could earn Montgomery tens of millions on the open market this winter.

Russell Steinberg: My esteemed colleagues have come up with the right answers, so I’ll just throw another name out there: Aaron Hicks. Hicksy was miserable early in the season with the Yankees — so much so that the Bronx Bombers released him in the middle of a seven-year, $70M deal. He caught on with the O’s and was actually productive, hitting .275 with an .806 OPS. So which Hicks will teams decide is the real one when he hits the open market in the offseason? October could hold the key.

How would you improve the MLB Playoff format?

GA: For me, it’s still just the fact that one of the better teams over the course of a 162-game regular season can see its season go to shambles with just two losses early on in the format. I get it — if teams just perform under pressure, then there’s nothing for us to be talking about. But it sucks that a team like the Tampa Bay Rays, who have the American League’s second-best record but just happen to be in the same division as the AL East-winning Baltimore Orioles, can have all their success over the course of months all erased in such a short series.

All that said, it is exciting stuff. If this format produces runs like Philly’s in 2022, then maybe it’s not all that bad.

SD: Build a schedule that gives the best regular-season teams more of an advantage. What happens if the Braves and Dodgers miss out on the NLCS for a second consecutive year? Sure, we want excitement, but a slate of 162 games takes a heck of a long time, and it means even more than it used to, thanks to the league’s move toward balanced scheduling. The league ended up outsmarting itself here by introducing too much entropy into the system.

Also: Create an alternate broadcast on MLB Network pairing Chris “Mad Dog” Russo with Joey Votto. You’re looking at Ricky Steamboat vs. Ric Flair levels of heat, folks.

SS: The current MLB playoff format has too many teams right now. I’d chop off a team from each league and make the regular season that much more meaningful, though one team getting a bye in each league is definitely appealing. I’d also lengthen the division series from best-of-5 to best-of-7.

RS: I’ve never liked the idea of teams making the postseason but not having a home game. The current MLB playoff format is more fair than the single-elimination Wild Card game of old, but this doesn’t quite cut it for me, either. So, I’m going to propose the opposite of what Shlomo suggested above. Major League Baseball will likely expand to 32 teams in the next few years. When that happens, just go to 16 playoff teams. No byes, 5-7-7-7 format. It’ll keep the regular season more exciting down to the final days and maybe — just maybe — finally force MLB to go back down to 154 games. Someone smarter than I will need to figure out how to convince the owners to allow that.

Which team(s) would benefit most from the MLB Playoff format?

GA: This postseason? I’d probably say the Houston Astros. Typically, this team is well ahead of the rest of the AL West, cruising to a playoff advantage by bypassing the Wild Card round. This season, however, they were in a lockstep battle with the Texas Rangers for the division crown that came down to the very last day of the regular season. In fact, both teams finished with 90-72 records, but because Houston took the season series, it’ll be sitting comfortably at home over Wild Card Weekend. I’m not sure they benefit that much, but they should consider themselves lucky they aren’t the ones having to win a best-of-three series against the Rays, who could ultimately win the World Series.

SD: Under the current format, it’s the same answer as a year ago: The Philadelphia Phillies. Because of the Division Series schedule’s generous approach to days off, the 1-2 punch of Zach Wheeler and Aaron Nola would be ready for the NLDS by Game 2. Given the extent to which their bats can erupt in a moment’s notice, they’re once again unusually well-suited for a deep run.

SS: No team won more home games in the American League this season than Tampa Bay’s 53. Even if the fans don’t show up, the Rays are at a distinct advantage with all three Wild Card series games at home against Texas.

On the NL side, Arizona stole 166 bases this season — second in baseball and the most among playoff teams. They were only caught 26 times all year. It’s not only playing a Milwaukee team that’s allowed 120 steals this season, the 17th most in the game during the regular season, but the Diamondbacks allowed the third-fewest steals led by catcher Gabriel Moreno, who threw out 16 of 33 attempted base stealers this season to lead baseball in caught stealing percentage. In the postseason, especially in a short series, every single tiny advantage matters.

RS: What if it’s the Toronto Blue Jays? Stick with me here. A team that won 89 games in the brutal AL East has to win two out of three on the road against a team from the woeful AL Central that won 87. Oh, and that AL Central team is on an 18-game postseason losing streak. If they win, yes, they have to deal with the Astros. But these Jays can hit and pitch well enough to beat a Houston team that actually has a losing record at home this year [insert comment about garbage cans].

Fearless prediction! Who is your World Series champion?

GA: If I’m picking with my heart, just as a fan watching this postseason, I’d love to see the Orioles and Phillies square off in the Fall Classic. First off, can we talk about how easy the travel would be? The cities are less than a two-hour drive from one another. Sure, it’ll be cold throughout — no West Coast warmup — but bouncing back and forth between Camden Yards and Citizen’s Bank Ballpark would be efficient and awesome.

But if I had to put money on it: Rays vs. Braves, with Atlanta taking it home for the second time in three years. The offense is too good. You can’t even field a unit that potent in MLB The Show. And while there are real concerns for the pitching staff heading into the playoffs, a Spencer Strider-led unit should be good enough with the power that lineup has.

SD: After depositing the Houston Astros into a trash can, the Baltimore Orioles become America’s Team (TM) and ride a wave in which they can do no wrong, defeating the Los Angeles Dodgers in six games.

SS: It’s chalky, but I’m picking a repeat of the 2021 World Series with the same result: the Atlanta Braves defeating the Houston Astros.

RS: There is no world in which I can pick the Astros to make the World Series, so instead, the Baltimore Orioles will play in the Fall Classic for the first time since 1983. Their magical run will capture the hearts of a nation until the Atlanta Braves rudely trample them en route to another championship, this one coming in five games.

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