When the Boston Red Sox locked up outfielder Roman Anthony to a massive contract extension this week, it sent a ripple across front offices and clubhouses around the league. But in Cincinnati, the message might hit even closer to home, particularly for Reds second baseman Matt McLain.
Anthony’s eight-year, $130 million deal with a club option that could extend it through 2034, and escalators pushing the value as high as $230 million, is just the latest in a growing list of young stars opting for financial security early. It’s also a reminder of what’s at stake when a player turns down a long-term offer in hopes of a bigger payday down the road. That’s the bet McLain made.
Prior to the start of the 2025 season, McLain reportedly turned down a contract extension from the Reds, a deal modeled in part after the long-term pact handed out to teammate Hunter Greene. The idea? Lock in a core of young talent while buying out arbitration years and a few free-agent seasons. But McLain passed. Whether it was a bet on himself or a belief that more money was coming, the gamble hasn’t aged well so far.
Reds 2B Matt McLain may be regretting turning down extension as Red Sox OF Roman Anthony cashes in
After missing all of 2024 due to left shoulder surgery, McLain entered the 2025 season needing to reestablish himself. But nearly four months in, the numbers have been underwhelming: a .650 OPS, 11 home runs, 38 RBI, and very little of the dynamic, power-speed impact he showed as a rookie.
And with each week that passes, it becomes harder to envision the Reds revisiting those extension talks anytime soon — at least not at the number McLain likely had in mind.
Meanwhile, Anthony’s deal reflects a growing industry trend: teams are willing to take risks on upside if the price is right, while players increasingly understand that early financial security can be life-changing, even if it means sacrificing a few dollars in free agency later.
For McLain, now 25, the window for “early extension” status is closing fast. Another underwhelming season or another injury could leave him heading into arbitration as a question mark, rather than a franchise building block.
There’s still time to turn things around. McLain’s pedigree, work ethic, and flashes of brilliance in 2023 suggest he can. But with every new long-term deal like Anthony’s, the risk McLain took by saying no becomes a little clearer.
Betting on yourself can be admirable. But sometimes, the house wins.
