Welcome to March, where the true “madness” is Jordan Montgomery’s ongoing free agency as it pertains to the Red Sox.

Here are some new questions (and a few repeats) to think about this week:

1. Which Red Sox player has the most on the line this season?

The funny thing about this question is that while every player has something on the line and must prove himself each year, it’s hard to say who truly has something on the line at this point. At the beginning of the offseason, I probably would’ve said Alex Verdugo, who’s entering free agency next fall, or Chris Sale, due to his lengthy injury history. Now, perhaps it’s Trevor Story who has the most to prove, especially if Marcelo Mayer has a strong season in Double-A and earns a promotion to Triple-A.

However, I’m more inclined to say that the Red Sox as a franchise, ownership, and front office, have the most on the line this season because they’ve officially backed themselves into a tight corner. They fired Chaim Bloom in mid-September, claiming they wanted to go in a different direction, but spent the offseason being fairly unaggressive in the pursuit of the upgrades leadership publicly stated the roster needed. Since spring training officially began on Feb. 13, they’ve been called out for their lack of spending on said upgrades by everyone from anonymous executives around the league, to Dustin Pedroia, to Jonathan Papelbon, to Rafael Devers. Or as Harry McAfee bemoans in “Bye Bye Birdie,” “You can talk and talk ’til your face is blue – Kids! – but they still do just what they want to do.”

The Red Sox are projected to finish last in the American League East once again, which would make a three-peat and four times in five years. Fans who’ve tried to trust the process and believe in the vision of “consistent contention” and homegrown sustainability are fed up by empty words, and many will likely retaliate by leaving the seats empty at America’s oldest and most beloved ballpark until they see measurable change.

If the team exceeds expectations this year, they’ll reduce the volume of criticism being heaped upon the club. But if they don’t win, it won’t be entirely their fault. At least, it shouldn’t be. Winning fixes a lot of things, but it doesn’t excuse ownership’s decision to promise “full throttle” only to then set an unnecessary spending limit.

2. For which player(s) would a repeat of their ’23 performance be acceptable?

Rafael Devers wasn’t satisfied with his year, and there were certainly a few too many cold stretches, but 33 home runs, 34 doubles, and 100 RBI are pretty excellent by most hitters’ standards. If Triston Casas can replicate the numbers he put up between June and September, when he hit .299 with a .953 OPS, 85 hits (16 doubles, two triples, and 18 home runs), 45 walks, and 77 strikeouts over his last 85 games, it will be a more than solid follow-up to the Rookie of the Year finalist performance he put on last season.

There won’t be any complaints if Chris Martin repeats his ’23 numbers: he posted a 1.05 ERA across 55 relief outings, and only issued eight walks across 51 1/3 innings. Likewise for Jarren Duran, who was excellent almost from the get-go until his unfortunate season-ending toe injury.

3. Will the Yellow Sox uniforms still bring the magic in ’24?

Somehow, those yellow City Connect uniforms managed to brighten up some of the darkest stretches of Red Sox baseball over the last few seasons. At some point, the magic has to run out though, right?

4. If MLB hadn’t implemented the Universal DH, which Red Sox pitcher would be the best hitter in NL ballparks?

I’ll never forget Rick Porcello smiling on second base after ripping a bases-clearing double in a July ’18 game against the Washington Nationals. That the broadcast had been mocking his lack of extra-base hits seconds before only added to the moment.

The universal designated hitter makes a lot of sense, but it also meant the end of such unique and unexpected happenstances.

5. Will any Red Sox pitcher throw a complete game this season?

Forget nine innings, last year a Sox pitcher getting through six was about as good as it got. The ’22 rotation put together five complete games – Nathan Eovaldi pitched two, and Brayan Bello, Nick Pivetta, and Michael Wacha each had one – but there weren’t any in ’21, either.

The Sox need their starters to pitcher deeper into games this year, but they need to be consistently effective and healthy throughout a full season, too. That’s a difficult tightrope to walk. But since complete games have become all but obsolete, it’s always thrilling to see a pitcher dominate they way they did back in the day.

6. Is Heinz ketchup the best Red Sox offseason acquisition?

Red Sox fans were overjoyed to see that Heinz ketchup is returning to Fenway Park concession stands this year, and it’s funny, but it’s also no laughing matter that such news elicited more fanfare on social media than any of the team’s offseason moves.

In fairness, fans always know what they’re getting from Heinz ketchup; they can’t say the same from the team. As McAfee says, “You know where you stand with a pet.”

7. Will the Red Sox sign Jordan Montgomery?

Over the weekend, USA Today’s Bob Nightengale reported that MLB executives “widely believe” Jordan Montgomery “will wind up” with the Sox. The Sox have been in communication with the free-agent starter, but that’s not exactly new.

As I said in at least one previous edition of “7 Questions,” I’ll keep asking this until he signs somewhere.