The Red Sox season may be over, but the postseason and impending offseason will give us plenty to ponder. My first seven questions of October:

1. How much does one loss really matter in a 162-game MLB season?

If I had a dollar for every time someone replied to one of my early-season tweets with some variation of, ‘Relax, it’s only April’ over the years, I’d estimate I’d have about a million dollars.

The stakes may not feel as high in April as they do in September, but ultimately, every game counts. Many teams struggled in the second half this year, including several of the current postseason teams. The Phillies, for example, racked up a hefty 62-34 record before the All-Star break, so going 33-33 after the break didn’t stop them from winning the NL East for the first time since 2011 and making their third consecutive postseason appearance.

The Red Sox weren’t mathematically eliminated from the Wild Card race until Game 158. If the bullpen had converted five of their 31 blown saves, the outcome of this season is a playoff berth.

2. Was the Boston bullpen a disaster waiting to happen?

While watching the Mets’ and Phillies’ bullpens duke it out on Sunday, I dove into the Red Sox relievers’ first- and second-half splits, and they were even worse than I remembered: a 3.66 ERA against 1,527 batters before the break, an MLB-worst 5.45 ERA against 1,129 batters after. A solid 66.7% save conversion in the first half, compared to 43.8% in the second, when the Red Sox were tied for the most save opportunities in the American League!

Losing Justin Slaten and Chris Martin to injuries was brutal. Adding Lucas Sims and Luis Garcia at the deadline, only to have both pitchers struggle and go on the injured list – on the same day, no less – was frustrating.

However, even with everyone fully healthy, I don’t think this year’s bullpen measures up to the top relief cores in this postseason. Cleveland’s ‘pen is absolutely terrifying, and the Padres bulked up big-time by acquiring Tanner Scott and Jason Adam during the season.

3. Why weren’t the Red Sox allowed to replace Kenley Jansen on the roster for the Rockies series?

Speaking of bullpens, when the Red Sox opened the second half with a road trip to Los Angeles and Colorado, they played a man down in the latter series.

Kenley Jansen has atrial fibrillation, an irregular heartbeat condition, and pitching in the altitude at Coors Field had already caused him severe medical distress multiple times in the past. His doctors told him that returning to the Rockies’ ballpark would put him at high risk. The Red Sox didn’t want to put him on the 7-day injured list, but they weren’t allowed to bring up another pitcher to replace him in Colorado, either. It’s impossible to know how much an additional arm would’ve helped, but maybe it means the Red Sox don’t blow the series opener 9-8 on a Rockies 10th-inning walk-off.

Either way, it certainly seems unfair that the only options were to play a man down or sacrifice Jansen for a full seven days. If anything qualifies as an extenuating circumstance, it’s a life-threatening heart condition.

4. What if Chaim Bloom had managed to get Mark Vientos for the Red Sox?

After a breakout season, New York Mets infielder Mark Vientos is proving he’s got the clutch factor on the big stage, too. Through his first five career postseason games, he’s 8-for-20 (.400) with five runs and seven RBI. He has three multi-hit games, including a three-hit performance in Game 2 of the NLDS: a double, two home runs, and four driven in.

In other words, it’s not hard to see why former Red Sox chief baseball officer Chaim Bloom tried to acquire Vientos. Multiple times, in fact; he wanted Vientos when the Mets were interested in JD Martinez before the ‘22 trade deadline, after the two clubs had come close to a Vientos-Christian Vázquez swap in a previous season.

Vientos also happens to be close with Triston Casas, a fellow American Heritage High School alum. Talk about an electric pairing.

5. Imagine if the Red Sox had signed Zack Wheeler in 2020.

An even bigger ‘What if?’

Wheeler’s five-year, $118 million contract for 2020-24 may have looked like a big risk at the time, but the Phillies have been amply rewarded for taking a chance on the former Met. In 133 regular-season starts over the span of his original deal – he signed an extension through ‘27 last March – Wheeler posted a 2.94 ERA and 1.031 WHIP, with 899 strikeouts across 829 ⅓ innings. He’s made 32 starts in three of the last four years, been an All-Star twice, and received NL Cy Young votes three times. He also owns a 2.18 ERA over 12 career postseason games, and has gone at least five innings in all 11 October starts. In Game 1 of the NLDS on Saturday, he gave the Phils seven scoreless innings and held the Mets to one hit.

Imagine all of that headlining the Red Sox rotation.

6. Would you rather: home-run derby or pitchers’ duel?

In an era full of moonshots, NLDS Game 2 between the Tigers and Guardians was a good old-fashioned pitchers’ duel. After Cleveland shut out Detroit 7-0 in Game 1, Presumptive AL Cy Young Tarik Skubal blanked the Guards for eight innings without issuing a walk. Kerry Carpenter won the game with a stunning three-run homer in the top of the ninth, the first bomb by a lefty against Cleveland closer Emmanuel Clase all year.

An instant classic.

7. Do you actually enjoy postseason baseball when it’s your favorite team?

There’s a big difference between wanting your favorite team to make it into the postseason and actually watching them attempt to go all the way to the finish line. Growing up in Boston, I hung on every single pitch of a Red Sox game, and my devotion amplified tenfold in October; the emotion-meter went from ‘Blessed’ to ‘Stressed’ very quickly. (Not that I’m complaining about four championships in 15 years.)

That’s why I’ve always enjoyed watching other teams’ games, too. They’re something of a palate cleanser: I’m able to appreciate great performances, such as the Tigers-Royals NLDS Game 2 pitching duel on Monday – without the risk of heartbreak.

Of course, the outcome won’t mean as much, either.