Lucas Giolito's 2023 season was truly a land of contrasts, and he officially turned the page on the sour last two months by signing a two-year, $38.5 million contract with the Boston Red Sox. It's a deal that's nowhere close to what he envisioned when he was garnering down-ballot Cy Young support in three consecutive seasons, but it's instructive in our continuing education regarding the changing landscapes of early-career extensions.
To refresh memories regarding Giolito's journey to the open market: Prior to the 2021 season, James Fegan said the White Sox offered Giolito a four-year, $50 million contract extension, with a club option for the 2025 season. I'm guessing the guaranteed money included a buyout because every team likes to defer salary when possible, so here's one stab at how the money might've been allocated:
- 2021: $4.15M
- 2022: $7.5M
- 2023: $13.35M
- FA1: $20M
- FA2: $22M club option ($5M buyout)
- Four-year total: $50M
- Five-year total: $67M
As I wrote then, it wasn't an unfair offer in terms of Giolito's earning potential over those years. Fegan noted that it would've been the highest four-year guarantee to a starting pitcher at that juncture of service time, and as it actually unfolded over Giolito's arbitration-eligible years, he would've made more money over the timeframe covered by the White Sox's extension than he made going year-to-year. The initial terms of his contract with the Red Sox don't change that.
- 2021: $4.15M
- 2022: $7.45M
- 2023: $10.4M
- FA1: $18M
- FA2: $19.5M player option ($1M buyout)
- Four-year total: $41.05M
- Five-year total: $59.5M
Yet that's not enough to say that Giolito made the wrong decision, because the player option for 2025 gives him a couple of avenues for that the White Sox's proposed extension wouldn't have afforded him. If he fully rebounds from his disastrous second half with an outstanding 2024, he can get a second crack at free agency before he could've taken his first bite at the apple under the proposed extension with the White Sox, and a fully realized four- or five-year deal would eliminate all second-guessing.
Conversely, the $19.5 player option for 2025 protects him against catastrophe in 2024, whether he underachieves or suffers a major injury, whereas the White Sox would've been within their rights to let him go like they did with Liam Hendriks.
The in-between outcomes are where Giolito could lose ground for good. If he's relegated to one- and two-year deals for the remainder of his career, then reaching free agency as early as possible didn't do anything for him financially.
In isolation, the White Sox can feel validated by drawing a hard line at four guaranteed years. It just doesn't do much for them going forward, either. They face a problem in the sense that a guy like Giolito would probably make that bet all over again. He's in good shape either way. He just bet on the opportunity to be in great shape, and while he couldn't cash in on his first attempt at a free agency windfall, he still might get there. What he lost in money he gained in time.
Whenever Tim Anderson finds his next MLB contract, he'll likely provide the counterpoint of delaying free agency. Had he not signed a six-year contract extension with two club options in 2017, he would've been a free agent as a 29-year-old coming off his second consecutive All-Star season, and his fourth year hitting .300. Instead, he's reached the open market after his third consecutive injury-altered season resulted in him being baseball's least valuable regular. He wouldn't have made Dansby Swanson money because he's not as durable or defensively sound, but now he won't even be making Jeimer Candelario money.
We'll return to this theme to tie up the loose ends when Anderson lands somewhere, so consider this Part 1 of a two-part study. As a standalone case, Giolito -- like Carlos Rodón before him -- shows why players who are good enough to bet on themselves feel increasingly comfortable doing so. If the White Sox aren't going to be comfortable paying for them earlier or later, then they have to get a whole lot better at developing those players and their replacements.
