For the second consecutive year, Matt Chapman stands as one of the top impending free agent hitters. Unless he suffers a significant injury in the next few weeks, he is all but assured to opt-out of the final two years and $36MM on his deal with the Giants.

Jon Heyman of the New York Post reported a couple weeks ago that San Francisco was hopeful of retaining the star third baseman on a new multi-year deal. Agent Scott Boras confirmed as much to Susan Slusser of the San Francisco Chronicle, telling her that the sides have had some discussions. President of baseball operations Farhan Zaidi framed things similarly, telling Slusser the parties have “had conversations” and “active dialogue” on a long-term arrangement.

That’s rather vague terminology that certainly doesn’t suggest anything is imminent. It’s nevertheless confirmation there’s some amount of mutual interest in keeping Chapman in San Francisco. He’s a California native who has a longstanding relationship with skipper Bob Melvin dating back to their time in Oakland.

Chapman hasn’t had any problem acclimating to Oracle Park. He takes a .245/.335/.442 batting line and his customarily strong defensive grades into tonight’s game in Seattle. He’s at 20+ homers for the fifth time in his career with a strong 11% walk percentage. Chapman’s 24.3% strikeout rate is a bit higher than the league mark but would be his lowest rate since 2019. It’s very good all-around production despite a slow start. Chapman limped to a .266 on-base percentage through the end of April. He has been one of the most productive infielders in the majors since then, posting a .253/.355/.461 line with 16 homers dating back to May 1.

It’s the inverse pattern to Chapman’s 2023 campaign. He was arguably the best player in the majors through the season’s first month last year. His offensive numbers plummeted after that and he hit the market with something of a down-arrow trajectory. Chapman had an easy call to decline a qualifying offer from the Blue Jays, but he and his camp at the Boras Corporation did not find the money they were seeking.  It wasn’t until the beginning of March that he inked a $54MM guarantee with multiple opt-outs.

Between a signing bonus, his salary, and a buyout (assuming he opts out), Chapman is making $20MM this year. That’s about what he’d have made if he’d taken the QO from Toronto — although the extra two years present more long-term security than the qualifying offer would have provided.

Chapman will presumably try again to land a deal that pushes into nine figures. He’ll play almost all of next season at age 32. It’s difficult but not impossible to pull a $100MM+ deal at that age. As shown on MLBTR’s Contract Tracker, there have been four nine-figure deals within the last decade for hitters who were 32 or older. Freddie Freeman’s six-year, $162MM pact led the way among free agent contracts. Jose Altuve, Paul Goldschmidt and Manny Machado signed extensions ranging between $125MM and $170MM in new money on five-year terms.

Those players were all better hitters than Chapman has been. As a plus defender at third base, he provides more value on that side of the ball than all of them, aside from maybe Machado. Teams could be wary about paying for defense into a player’s mid-30s.

A five-year term for Chapman would run through his age-36 season. That’s the point through which Kris Bryant and Anthony Rendon were paid on seven-year contracts (both of which have been disasters for the team). Chapman certainly isn’t going to approach Rendon’s $35MM annual salary. Bryant’s $26MM AAV is a more realistic target, albeit on a what’d likely be a four- or five-year term instead of seven.

Josh Donaldson and DJ LeMahieu each signed through age-37 as free agent third basemen. Both guarantees checked in just south of $100MM. Those contracts are a few years old and were both signed after the player declined a qualifying offer, thereby attaching draft compensation. The Giants cannot make Chapman a QO — the CBA prevents a player from receiving more than one in his career — so he’d hit the market entirely unencumbered. Barring some kind of hometown discount, Chapman presumably wouldn’t be interested in forgoing a free agent trip for less than the Donaldson and LeMahieu guarantees.

Alex Bregman leads the impending free agent class at third base. Chapman is the clear #2 option and the class drops off dramatically from there. Last winter’s group was even shallower. Assuming one considers Cody Bellinger primarily an outfielder rather than a first baseman, Chapman’s $54MM guarantee led all infielders.

As Slusser observes, a Chapman extension may need to be San Francisco’s biggest investment under this front office. The Giants have only signed one nine-figure deal since they hired Farhan Zaidi as president of baseball operations during the 2018-19 offseason: last winter’s six-year, $113MM pact for 25-year-old center fielder Jung Hoo Lee. They’ve taken plenty of bigger swings and were a failed physical away from signing Carlos Correa for $350MM, but they’ve yet to actually land a domestic free agent on a long-term deal. They’ve been much more amenable to shorter-term pickups with opt-outs for players whose markets didn’t develop as they’d hoped (e.g. Carlos Rodón, Michael Conforto, Blake Snell, Chapman).

The Giants have around $132MM in guaranteed money for next season. Expected opt-outs for Snell and Chapman would knock that down to roughly $85MM. Lee, Logan Webb, Robbie Ray (assuming he doesn’t opt out this year) and Jordan Hicks are the only players signed beyond next year. That doesn’t include arbitration projections for Mike Yastrzemski, Thairo Estrada, Tyler Rogers, LaMonte Wade Jr. and Camilo Doval. Estrada and Yastrzemski are potential trade or non-tender candidates. The Giants should have a good amount of payroll flexibility even if they retain everyone from their arbitration group.