The Windup Newsletter ⚾ | This is The Athletic’s MLB newsletter. Sign up here to receive The Windup directly in your inbox.How far are you looking ahead? To today’s nine-game slate, the postseason or even the offseason?In this week’s mailbag, today staging a Windup takeover, I let my mind wander into the latter. I focused on answering questions regarding contracts, targets, extensions and what it will take to get that one player your team really wants.Below are a few highlights. (Submissions were edited for clarity and brevity.)And as a reminder: Levi is out for the next two weeks, playing sandlot baseball at the Field of Dreams, among other spots.MLB Mailbag: Let’s answer your contract questionsJazz Chisholm Jr. free agency: Is he back in the Bronx on a 1-year prove-it deal? — Nick B.It sure doesn’t feel like it right now, but Chisholm is still on pace for a three-win season, which is not bad to consider while enduring the worst slump of your career. Trevor Story signed for six years and $140 million off that kind of season.The question for Chisholm will be how teams balance the one-year sample versus the larger one. If he finishes this year around 3.0 WAR, he’ll have 11.5 WAR over the last three years — more than Cody Bellinger had when he signed his $162 million deal with the Yankees last winter and close to the number Corey Seager had when he signed his $325 million contract with the Rangers.However, I’ve generally found that teams heavily weigh the season entering free agency. Bellinger was close to a five-win season; Seager was at 3.6 but had been hurt.I would expect teams would be interested in multi-year deals for Chisholm, but probably in the four-year range (and maybe between $20 million and $25 million per year). That means that, yes, a team with the Yankees’ resources should absolutely extend him the qualifying offer. (This entire paragraph, I should acknowledge, does require Chisholm to break out of this slump sometime between now and the end of the Yankees’ season.)If Chisholm wants to bet on himself to reel in a huge deal, well, there’s a blueprint. The last second baseman whose numbers resembled Chisholm’s did take a one-year, prove-it deal. Marcus Semien proved it in Toronto, setting a new record for home runs by a second baseman, and he signed for seven years and $175 million one winter later with Texas.How will both existing contracts and ones signed between now and Dec. 1 be affected by the new CBA? I understand that no one knows what the new deal will include for salary constraints, but GMs must be thinking about how past and future contracts will be impacted. — Rosemary P.Yep, nobody knows.If a salary cap and floor are instituted, they could be phased in over a few years and could include amnesty provisions that allow teams to get out of one onerous contract that would otherwise count against the cap, etc.