Why hasn’t some team tried it yet?

I can think of a few reasons:

1. Until recently, nobody but the Yanks passed the CBT other than by a few million for a season or two. There was no incentive. Possibly now this would make sense for the Padres -- land of the Tatis and Bogaerts contracts.

2. At best you piss off the league and they institute a rule that stops it. At worst, you piss off the league and they void the contract and none of the other owners will talk to you at the winter meetings.

3. It might take a while but eventually it catches up to you because you've got your star players from 20, 15, 10 and 5 years ago all on the payroll at the same time as your star player now and your CBT hit will be substantially higher than it otherwise would have been.

Mary Poppin's carpetbag:
"Mary Poppins carried a carpetbag just like Aunt Ellie's but the nanny's bag became a magical carry-all that contained an apron, a packet of hairpins, a bottle of scent, a small folding armchair, a packet of throat lozenges, a large bottle of dark red medicine, seven flannel nightgowns, one pair of boots, a set of dominoes, two bathing caps, one postcard album, one folding camp bedstead, blankets and an eiderdown."
Imagine an ump going through that.

I feel like a team did try it, just this offseason. Did the Padres try to offer Bogaerts something like a 16-year contract, and the league stepped in and said, no, you can't do that, it's clear manipulation of the CBT? It was one of this year's free agents, but I can't find any reporting on it. Was it Judge? It's kind of driving me crazy.

I feel like a team did try it, just this offseason. Did the Padres try to offer Bogaerts something like a 16-year contract, and the league stepped in and said, no, you can't do that, it's clear manipulation of the CBT? It was one of this year's free agents, but I can't find any reporting on it. Was it Judge? It's kind of driving me crazy.

I don't think that happened, although there was a discussion here about teams doing something like that.

The closest thing was probably the Giants contract with Correa (13 years, $350), but that was cancelled due to medical concerns, not the league stepping in.

I feel like a team did try it, just this offseason. Did the Padres try to offer Bogaerts something like a 16-year contract, and the league stepped in and said, no, you can't do that, it's clear manipulation of the CBT? It was one of this year's free agents, but I can't find any reporting on it. Was it Judge? It's kind of driving me crazy.

You're thinking of the offer the Padres were reportedly going to offer Judge. From MLBTR:

Jon Heyman of the New York Post added some clarity on the matter last night, reporting the Padres were preparing an offer to Judge that’d have reached or exceeded $400MM over a whopping 14-year term. However, Heyman further hears Major League Baseball would have been prepared to veto such an arrangement if the sides had agreed upon it. Of course, it proved to be a moot point once Judge decided he wanted to return to the only organization he’s ever known.

MLB vetoing a record-breaking contract would’ve made for a fascinating story. The league’s justification for doing so would’ve been the contract length was an artificial means for the team of working around the competitive balance tax.

[...]

It’s understandable MLB would be wary of a blatant workaround to the luxury tax, which is designed to disincentivize spending among teams with already large payrolls. Yet it’s also somewhat curious to hear they’d have stepped in to veto that kind of proposal to Judge considering some large-market teams have already increasingly taken to a variation of this strategy: longer-term deals at comparatively lesser annual salaries to lower the CBT obligations.

[...]

Of course, the league isn’t in position to preemptively create fixed rules to govern how much tinkering with the AAV constitutes luxury tax manipulation. MLB is left to evaluate things on a case-by-case basis. A 13-year deal for Harper that runs through his age-38 season was acceptable, as was an 11-year pact that goes through Turner’s age-40 campaign. A 14-year contract to take Judge through his age-44 season would evidently not have passed muster.

The Judge situation at least raises the possibility of MLB intervening on future deals it considers to be circumventions of the tax. That’d have the potential to lead to a battle with the union.

It's obviously a difficult thing to legislate, at least if you want union agreement. The easy way to do it is either "no contracts longer than 10 playing years" (i.e. you can still defer salary you just can't manipulate the CBT hit) or "no multi-year contracts signed prior to age 40 that run past age 40" or similar. But why should the union agree to that? If the Angels want to rock up with a 18/$600 contract for Ohtani -- that's pretty clearly not extreme CBT games, we can't say for sure he won't still be playing at 45, etc.

It seems to me the CBT shenanigans work better if you've got a guy you'd sign for 7/$200 and instead sign him for 25/$300. This would be most obvious for somebody like Miguel Cabrera. Signing him to that extension wasn't a great idea (and the Tigers would soon not be the least bit worried about their CBT threshold) but it would usually benefit the team to make 8/$240 (or whatever it was) into 20/$300 (or whatever keeps the NPV similar). Don't "force" the team to choose between letting an icon go or gambling huge money on an aging player while also taking a CBT hit -- get the CBT hit out of it.

I suppose another way around this is an NBA style rule where teams can extend their own superstar but cap the CBT hit from that contract -- for example all such contracts are taxed at the minimal rate. (You need some math stuff to decide how much of the overage comes from each contract.)

Thank you, NaOH, I was all around it....I knew I wasn't crazy!

You know the writer is just showing off when they use "civic religion", "de rigeur" and "Full Kovalchuk" in the same article.

They do get around this with deferred money dropping the CBT hit. Not sure what signing someone through age 45 does differently?

Not sure what signing someone through age 45 does differently?

Spreads it out even more and more obviously. There is a very good chance that Bogaerts will still be on the field at 39, even without this contract (and a very, very good chance with this contract). But he's not gonna be out there at 45 or even 42 and "everyone" "knows" that so it's too obvious it's just a game to reduce CBT.

It's a bit like everybody knows the Cubs manipulated Bryant's service time but to actually rule in his favor requires showing it wasn't for legit baseball reasons. It makes perfect sense that Mookie was signed through 39, Trout through ... 39?, Pujuls through 42 and obviously the Tigers didn't sign Cabrera through 40 to defer the money. So how can MLB say the Padres aren't making a legit baseball decision to sign Xander through 39? But through 45? Different story.