This risky short-term contract design could land Jack Flaherty with the Angels

A popular model has been established to land top-end pitchers on short term deals, but it is not without risk.
World Series - New York Yankees v Los Angeles Dodgers - Game 1
World Series - New York Yankees v Los Angeles Dodgers - Game 1 | Harry How/GettyImages

The hot stove has started to heat back up after a period of frigidity following the close of the Winter Meetings. We saw the Roki Sasaki sweepstakes come to its inevitable conclusion. We have seen the top two remaining outfield bats – Anthony Santander and Jurickson Profar find new homes. But we've yet to see the Angels make a significant move since early November.

The Halos still have needs, with perhaps the biggest being in the starting rotation where unproven youth and questionable veterans hold down the fort. The pitching market has mostly dried up, as what's left are older veterans and a hurler in Nick Pivetta whose results don't match his peripherals (plus is bogged down by the qualifying offer).

Then there's Jack Flaherty. A front-end starter who has youth, top-end upside, and a World Series ring on his side, as well as being unencumbered by the qualifying offer. On the surface, he should have been snatched up on a lucrative, long-term deal months ago, but there's more than meets the eye.

Flaherty has struggled with injuries, and his first healthy season, 2023, was not good as he pitched to a 4.99 ERA. Last year, he seemingly erased those performance concerns as he posted a 3.17 ERA, and helped the Dodgers march to a World Series title after a midseason trade.

Still, there are some underlying concerns with his fastball velocity and break on his slider that raise questions about whether he can repeat last year's performance in 2025. This all has led Flaherty to consider short-term, high AAV contract offers.

Players in similar situations have shown a preference for a "one-plus-one" type of contract – essentially a one-year deal at a high AAV with a player option for a second year at a similarly high rate. This gives the player the best of both worlds, the ability to rebuild value and immediately test the market to following year while also providing a sense of financial security should things go awry.

The Angels likely could land Flaherty if they made an aggressive offer in that vein. In many ways, it would be a wise move, but not one without some risk.

This contract model is great when it works, but could present a risk to the Angels

As this type of contract has become envogue, it's important to look at how it has worked out with starting pitchers in particular. Two particular examples stand out.

Carlos Rodon began his career with the Chicago White Sox as a promising young starter who then struggled with injuries and inconsistency before putting together a sterling 2021 campaign where he posted a 5.0 fWAR ahead of free agency.

The past injuries and erratic performance scared teams off from giving him a long-term deal, and he ultimately settled for a two-year $44 million contract with the San Francisco Giants in March of 2022. That second year though was really a player option for $22.5 million.

Rodon put up the best season of his career in 2022, pitching to a 2.88 ERA and posting 6.2 fWAR. He promptly declined his option at the end of the season and inked an eight-year $162 million contract with the New York Yankees where injuries and inconsistency have reared their head again.

Still, the San Francisco Giants will certainly tell you that they got their money's worth, and the Yankees are now left holding the bag that everyone hoped to avoid the previous year.

The next case study is that of Jordan Montgomery. Unlike Flaherty and Rodon, Montgomery came up with the New York Yankees and established himself as a consistent mid-rotation starter. After being traded a couple of times, he found himself seemingly unlocking a new level in 2023 when he pitched to a 3.20 ERA and posted a 4.3 fWAR while, like Flaherty, was traded midseason and played an integral role for the ultimate World Series champion Texas Rangers.

Teams didn't necessarily buy into his sudden emergence as a top-of-the-rotation arm, and he settled for a one-year $25 million dollar contract with a player option for another year at $22.5 million last March with the Arizona Diamondbacks.

Unlike Rodon, Montgomery was an unmitigated disaster in the desert and finished the 2024 season with a sky-high 6.23 ERA. He promptly picked up his option this offseason, securing his $22.5 million, significantly more than he'd make on the open market, much to the ire of the Diamondbacks who are now desperate to trade him.

Flaherty seems to have come to the realization that this is his market much sooner than the other two did, so it may not take up until the eve of the regular season for him to sign. However, if he were to accept a deal like Montgomery and Rodon, it would not come without risk.

The Angels have a severe need and Flaherty is objectively the best option, but their extreme risk avoidance may put them out of the running. If the team does pursue and land Flaherty, it could work out swimmingly, or it could go down as yet another poor free-agent signing. But at least it won't hamstring the team for the better part of a decade like some of their other big whiffs.

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