Shohei Ohtani

Shohei Ohtani is a generational talent with major FA bust potential

Could Shohei Ohtani join a growing list of superstars who haven't lived up to their price tag?

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News that the Angels might, possibly, but probably not, maybe trade Shohei Ohtani before the August 1 deadline sent only tiny ripples across the game for multiple reasons.

For one, how do you trade -- and this is not hyperbole -- the greatest all-around player the game has ever produced? Much of baseball remains skeptical the reeling Angels will pull the trigger when they're only a game under .500. For another, who can actually afford the prohibitive player and prospect cost for what's almost certainly going to be a two-month rental? And finally, the number of teams with the will to offer Ohtani the $600 million it's going to take to secure his services long term is very, very small. We're talking Dodgers vs. Mets and everyone else insisting they tried their best.

If this is where you expect me to blast the Red Sox for thinking small in the face of a generational talent, not so fast. Time and time and time again, baseball's biggest contracts end up being its worst investments, with the dollars and years escalating to absurd levels.

It was one thing to write off a couple of dead seasons at the end of an eight-year contract like the ones Manny Ramirez and Mark Teixeira signed a generation ago. It's quite another to do so for 12 or 13 years, which is becoming the norm.

Cautionary tales abound. Albert Pujols. Miguel Cabrera. David Price. Stephen Strasburg. Anthony Rendon.

All billed as saviors, all wildly overpaid. Only Price went on to win a World Series, and you'll have to decide if the $217 million was worth it to tolerate everything else that came with that little ray of sunshine.

So forgive me for being skeptical of Ohtani's long-term value. The first question any team should ask before it commits massive free-agent dollars is if the target of their affections is built to last. There's no way to answer that question for Ohtani with any certainty, because no one in the modern era has pitched every fifth day and hit the other four.

Ohtani has already had Tommy John surgery, and it's fair to ask how long the 29-year-old can last while throwing the ball 100 mph and hitting it 118. In short order, Ohtani could become a $50 million DH, and maybe he's worth it, but man, what a risk.

As a thought exercise, ask the teams with the 10 highest-paid players ever if they'd do the deals again.

No. 1 is Ohtani's teammate, Mike Trout, at $426.5 million through 2030. He just broke his hamate and will miss at least a month, continuing a string of injury woes that dates back four years. Since winning his third MVP in 2019 -- a season, incidentally, that ended early because of foot surgery – Trout has missed more than 175 games. He's great when he plays, but what's he going to look like in three years, let alone seven?

No. 2 is Mookie Betts (12 years, $365 million), and the Dodgers have absolutely no complaints there. He's in the midst of his best season since his 2018 MVP, and he shows no signs of slowing down. He has already smashed 26 homers while playing all over the field.

No. 3 is Aaron Judge (9 years, $360 million), who just tore a toe ligament crashing through a fence in Los Angeles. That's a bad omen for such a giant human being who's already 31 years old.

No. 4 is Francisco Lindor (10 years, $341 million) and he's been OK with the Mets, but certainly not the perennial Gold Glover and All-Star he was in Cleveland.

No. 5 is Fernando Tatis Jr. (14 years, $340 million), a supremely talented youngster who has already (A) had to leave shortstop for right field because of a shoulder injury, (B) misled the Padres about an offseason motorcycle accident that required surgery, and (C) been popped 80 games for steroids. He's insanely talented, but mercurial, to say the least.

No. 6 is Bryce Harper (13 years, $330 million), who has already won an MVP and reached a World Series with the Phillies, but is currently limited to DHing after undergoing Tommy John.

Nos. 7-8 is a tie between Giancarlo Stanton (13 years, $325 million) and Corey Seager (10 years, $325 million). The former is a one-dimensional slugger, while the latter is having a monster year in Texas after a mediocre debut.

No. 9 is Gerrit Cole (9 years, $324 million), who has single-handedly kept the Yankees rotation afloat. He has been worth the money thus far.

That leaves a tie at No. 10 between San Diego's Manny Machado and Philadelphia's Trea Turner, who each recently signed $300 million deals. The former has already delivered a pair of top-three MVP finishes in San Diego, while the latter is off to a rough start in Philly. (Machado signed a new 11-year extension worth $350 million in February.)

The only guys on that list you'd definitely still pay are Betts, Cole, and Machado. Maybe Seager. And we're not even including Xander Bogaerts, who already needs cortisone shots four months into an 11-year deal with the Padres, or Alex Rodriguez, whose $275 million contract ended in disgrace.

So forgive me for thinking the Red Sox would be crazy to surrender some combination of Marcelo Mayer, Jarren Duran, and/or Brayan Bello to acquire the greatness that is Ohtani for the stretch run, let alone make him the highest-paid player in history.

He'd be incredible to watch in the short term, but if you allow yourself to think beyond tomorrow, suddenly he doesn't feel like the best long-term investment.

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